67:
223:
II/IV enzyme (the target in most Gram-positive bacteria) or DNA gyrase (the target in Gram-negative bacteria), preventing the bacteria from unwinding their DNA and undergoing either DNA replication or transcription. The majority of drugs in clinical use are actually quinoline derivatives that belong to the subset fluoroquinolones, which have a fluorine atom attached to the central ring system, often at the C-6 or C-7 position.
222:
The synthesis of 4-hydroxyquinolines and 4-quinolones is of great importance to a variety of fields, but most notably to the medical sciences due to their use as chemotherapeutic bactericidal drugs through their ability to kill bacteria. This mechanism involved disabling the bacterial topoisomerase
121:
of the molecule via an electrocyclic ring closing. For this step, the Schiff base must be heated to ~250 °C for the ring closure to occur. Furthermore, the type of solvent used is very important to ensuring high yields of the 4-hydroxyquinoline product. In the early work, the cyclization was
203:β-keto acid anilide product (albeit in less than ideal yields). Continuation of this reaction using the Conrad-Limpach mechanism led to the synthesis of 2-hydroxyquinoline. The initial synthesis of 2-hydroxyquinoline from a β-ketoanilide was reported in 1886 as the
122:
accomplished by heating the Schiff base without a solvent and the yields were very moderate (below 30%). Limpach reported many years later that the yields in the cyclization were raised to 95% in many cases when an inert solvent, such as
212:
3797:
436:
Baba, A.; et al. (1996). "Studies on disease-modifying antirheumatic drugs: Synthesis of novel quinoline and quinazoline derivatives and their anti-inflammatory effect".
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399:"Cytotoxicity of quinolones toward eukaryotic cells. Identification of topoisomerase II as the primary cellular target for the quinolone CP-115,953 in yeast"
129:
The Conrad-Limpach reaction mechanism also involves multiple keto-enol tautomerizations, all of which are catalyzed through the use of a strong acid, often
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observed that under higher temperatures (approximately 140 °C) the aniline would actually attack the ester group of the β-ketoester, leading to the
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1911:
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group. When Conrad and
Limpach first observed this reaction in 1887, it was run at room temperature, and gave high yields of β-aminoacrylate: the
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showed that many quinoline derivatives show promise in their anti-inflammatory effects for the treatment of arthritis, Schmidt
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is the final product of the Conrad–Limpach synthesis. Although the reaction product is often shown as a hydroxyquinoline (
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delved into the progress behind treating drug-resistant malaria using 4-hydroxyquinoline derivatives, and Lui-Zai Gang
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63:(1848–1920) and Leonhard Limpach (1852–1933) in 1887 while they were studying the synthesis of quinoline derivatives.
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502:
LUO Zai-gang; ZENG Cheng-chu; WANG Fang; HE Hong-qiu; WANG Cun-xin; DU Hong-guang; HU Li-ming (2009).
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167:) predominates. For the purposes of this page and based on the reaction mechanism as it is shown in
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Perhaps the most important step (and the rate-determining step) in the reaction mechanism is the
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382:
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179:
In the reaction of aniline with a β-ketoester, there are two possible sites of attack for the
99:. The mechanism concludes with the removal of an alcohol, a series of proton transfers, and a
52:
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3722:
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617:
504:"Synthesis and Biological Activities of Quinoline Derivatives as HIV-1 Integrase Inhibitors"
478:
445:
410:
352:
344:
295:
264:
207:. Therefore, the overall reaction is sometimes called the “Conrad-Limpach-Knorr reaction”.
3817:
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998:
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111:
788:
758:
255:
Conrad M.; Limpach L. (1887). "synthesen von
Chinolinderivaten mittelst Acetessigester".
195:. The reaction then continued to give the final product of 4-hydroxyquinoline. However,
482:
3822:
3732:
3671:
2763:
2673:
2643:
2418:
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2010:
1787:
1657:
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357:
332:
315:
Li, Ji Jack (2009). Name
Reactions, 4th ed. Berlin: Springer-Verlag. pp. 133–134.
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226:
There are also many non-antibacterial medical uses for 4-hydroxyquinoline. Baba
123:
88:
44:
3656:
3183:
2533:
622:
591:
575:
348:
299:
268:
169:
Name
Reactions: A Collection of Detailed Mechanisms and Synthetic Applications
148:
118:
333:"Survey of Solvents for the Conrad–Limpach Synthesis of 4-Hydroxyquinolones"
160:
104:
36:
366:
490:
457:
424:
1063:
733:
164:
156:
238:
studied the use of quinoline derivatives as HIV-1 integrase inhibitors.
723:
180:
80:
24:
449:
469:
Schmidt, L.H. (1969). "Chemotherapy of the Drug-Resistant
Malarias".
184:
283:
188:
134:
566:, Coll. Vol. 3, p. 593 (1955); Vol. 29, p. 70 (1949). (
1107:
626:
130:
87:. The newly formed oxide is then twice protonated to form the
153:
a substituted 4-hydroxyquinoline or a substituted 4-quinolone
65:
331:
Brouet, J.C.; Gu, S.; Peet, N.P.; Williams, J.D. (2009).
51:). The overall reaction type is a combination of both an
107:, the final product of the Conrad–Limpach synthesis.
3798:
Erlenmeyer–Plöchl azlactone and amino-acid synthesis
3705:
3532:
3167:
2682:
2177:
2094:
1974:
1854:
1806:
1116:
171:by Ji Jack Li, the product is a hydroxyquinoline.
2859:Divinylcyclopropane-cycloheptadiene rearrangement
175:Regioselectivity of β-ketoester: Knorr variation
147:With much of the literature on the synthesis of
83:on the keto group of the β-ketoester to form a
3119:Thermal rearrangement of aromatic hydrocarbons
1753:Thermal rearrangement of aromatic hydrocarbons
397:Elsea, SH.; Osheroff, N.; Nitiss, JL. (1992).
381:. Royal Society of Chemistry. pp. 48–49.
284:"Ueber das γ‐Oxychinaldin und dessen Derivate"
3848:Lectka enantioselective beta-lactam synthesis
638:
8:
3627:Inverse electron-demand Diels–Alder reaction
1448:Heterogeneous metal catalyzed cross-coupling
2969:Lobry de Bruyn–Van Ekenstein transformation
3529:
1803:
1104:
645:
631:
623:
3459:Petrenko-Kritschenko piperidone synthesis
2914:Fritsch–Buttenberg–Wiechell rearrangement
414:
356:
3622:Intramolecular Diels–Alder cycloaddition
247:
151:, there is some discrepancy on whether
79:The mechanism begins with an attack of
3642:Metal-centered cycloaddition reactions
3294:Debus–Radziszewski imidazole synthesis
1238:Bodroux–Chichibabin aldehyde synthesis
3788:Diazoalkane 1,3-dipolar cycloaddition
3692:Vinylcyclopropane (5+2) cycloaddition
3597:Diazoalkane 1,3-dipolar cycloaddition
3369:Hurd–Mori 1,2,3-thiadiazole synthesis
2864:Dowd–Beckwith ring-expansion reaction
2031:Hurd–Mori 1,2,3-thiadiazole synthesis
944:LFER solvent coefficients (data page)
7:
2599:Sharpless asymmetric dihydroxylation
1836:Methoxymethylenetriphenylphosphorane
2724:Allen–Millar–Trippett rearrangement
483:10.1146/annurev.mi.23.100169.002235
3863:Nitrone-olefin (3+2) cycloaddition
3858:Niementowski quinazoline synthesis
3647:Nitrone-olefin (3+2) cycloaddition
3572:Azide-alkyne Huisgen cycloaddition
3434:Niementowski quinazoline synthesis
3189:Azide-alkyne Huisgen cycloaddition
2494:Meerwein–Ponndorf–Verley reduction
2046:Leimgruber–Batcho indole synthesis
59:. This reaction was discovered by
14:
3687:Trimethylenemethane cycloaddition
3389:Johnson–Corey–Chaykovsky reaction
3254:Cadogan–Sundberg indole synthesis
3234:Bohlmann–Rahtz pyridine synthesis
3194:Baeyer–Emmerling indole synthesis
2001:Cadogan–Sundberg indole synthesis
1493:Johnson–Corey–Chaykovsky reaction
183:nitrogen atom: the very reactive
3783:Cook–Heilbron thiazole synthesis
3612:Hexadehydro Diels–Alder reaction
3439:Niementowski quinoline synthesis
3269:Cook–Heilbron thiazole synthesis
3214:Bischler–Möhlau indole synthesis
3124:Tiffeneau–Demjanov rearrangement
2754:Baker–Venkataraman rearrangement
1912:Horner–Wadsworth–Emmons reaction
1583:Mizoroki-Heck vs. Reductive Heck
1468:Horner–Wadsworth–Emmons reaction
979:Neighbouring group participation
210:
110:
3319:Fiesselmann thiophene synthesis
3149:Westphalen–Lettré rearrangement
3129:Vinylcyclopropane rearrangement
2959:Kornblum–DeLaMare rearrangement
2604:Epoxidation of allylic alcohols
2514:Noyori asymmetric hydrogenation
2449:Kornblum–DeLaMare rearrangement
2124:Gallagher–Hollander degradation
560:Reynolds, G. A.; Hauser, C. R.
511:Chem. Res. Chinese Universities
3778:Chichibabin pyridine synthesis
3264:Chichibabin pyridine synthesis
3224:Blum–Ittah aziridine synthesis
3059:Ring expansion and contraction
1328:Cross dehydrogenative coupling
282:Conrad M.; Limpach L. (1887).
1:
3748:Bischler–Napieralski reaction
3706:Heterocycle forming reactions
3359:Hemetsberger indole synthesis
3219:Bischler–Napieralski reaction
3134:Wagner–Meerwein rearrangement
3104:Sommelet–Hauser rearrangement
3084:Seyferth–Gilbert homologation
2949:Ireland–Claisen rearrangement
2944:Hofmann–Martius rearrangement
2704:2,3-sigmatropic rearrangement
2319:Corey–Winter olefin synthesis
2244:Barton–McCombie deoxygenation
1887:Corey–Winter olefin synthesis
1841:Seyferth–Gilbert homologation
1708:Seyferth–Gilbert homologation
416:10.1016/S0021-9258(18)42185-0
126:, was used for the reaction.
3853:Lehmstedt–Tanasescu reaction
3813:Gabriel–Colman rearrangement
3768:Bucherer carbazole synthesis
3763:Borsche–Drechsel cyclization
3743:Bernthsen acridine synthesis
3728:Bamberger triazine synthesis
3713:Algar–Flynn–Oyamada reaction
3424:Nazarov cyclization reaction
3289:De Kimpe aziridine synthesis
3244:Bucherer carbazole synthesis
3239:Borsche–Drechsel cyclization
3009:Nazarov cyclization reaction
2989:Meyer–Schuster rearrangement
2919:Gabriel–Colman rearrangement
2669:Wolffenstein–Böters reaction
2554:Reduction of nitro compounds
2404:Grundmann aldehyde synthesis
2209:Algar–Flynn–Oyamada reaction
1618:Olefin conversion technology
1613:Nozaki–Hiyama–Kishi reaction
1408:Gabriel–Colman rearrangement
1298:Claisen-Schmidt condensation
1243:Bouveault aldehyde synthesis
187:group, or the less reactive
70:The Conrad-Limpach synthesis
3947:Quinoline forming reactions
3828:Hantzsch pyridine synthesis
3607:Enone–alkene cycloadditions
3429:Nenitzescu indole synthesis
3349:Hantzsch pyridine synthesis
3314:Ferrario–Ackermann reaction
2964:Kowalski ester homologation
2929:Halogen dance rearrangement
2774:Benzilic acid rearrangement
2199:Akabori amino-acid reaction
2159:Von Braun amide degradation
2104:Barbier–Wieland degradation
2056:Nenitzescu indole synthesis
2036:Kharasch–Sosnovsky reaction
1927:Julia–Kocienski olefination
1831:Kowalski ester homologation
1528:Kowalski ester homologation
1503:Julia–Kocienski olefination
1258:Cadiot–Chodkiewicz coupling
1183:Aza-Baylis–Hillman reaction
1128:Acetoacetic ester synthesis
839:Dynamic binding (chemistry)
829:Conrotatory and disrotatory
804:Charge remote fragmentation
377:Sainsbury, Malcolm (2001).
201:thermodynamically preferred
159:), it is believed that the
3968:
3893:Robinson–Gabriel synthesis
3843:Kröhnke pyridine synthesis
3677:Retro-Diels–Alder reaction
3617:Imine Diels–Alder reaction
3404:Kröhnke pyridine synthesis
3019:Newman–Kwart rearrangement
2994:Mislow–Evans rearrangement
2904:Fischer–Hepp rearrangement
2849:Di-π-methane rearrangement
2629:Stephen aldehyde synthesis
2364:Eschweiler–Clarke reaction
2081:Williamson ether synthesis
1398:Fujiwara–Moritani reaction
1303:Combes quinoline synthesis
1268:Carbonyl olefin metathesis
969:More O'Ferrall–Jencks plot
894:Grunwald–Winstein equation
864:Electron-withdrawing group
799:Catalytic resonance theory
613:Combes quinoline synthesis
97:electrocyclic ring closing
3903:Urech hydantoin synthesis
3883:Pomeranz–Fritsch reaction
3808:Fischer oxazole synthesis
3542:1,3-Dipolar cycloaddition
3514:Urech hydantoin synthesis
3484:Reissert indole synthesis
3469:Pomeranz–Fritsch reaction
3399:Knorr quinoline synthesis
3329:Fischer oxazole synthesis
3259:Camps quinoline synthesis
3179:1,3-Dipolar cycloaddition
3079:Semipinacol rearrangement
3054:Ramberg–Bäcklund reaction
3039:Piancatelli rearrangement
2979:McFadyen–Stevens reaction
2734:Alpha-ketol rearrangement
2489:McFadyen–Stevens reaction
2434:Kiliani–Fischer synthesis
2354:Elbs persulfate oxidation
2279:Bouveault–Blanc reduction
2239:Baeyer–Villiger oxidation
2071:Schotten–Baumann reaction
1947:Ramberg–Bäcklund reaction
1826:Kiliani–Fischer synthesis
1668:Ramberg–Bäcklund reaction
1653:Pinacol coupling reaction
1648:Piancatelli rearrangement
1543:Liebeskind–Srogl coupling
1393:Fujimoto–Belleau reaction
1110:List of organic reactions
974:Negative hyperconjugation
719:
661:
349:10.1080/00397910802542044
300:10.1002/cber.188702001216
269:10.1002/cber.188702001215
205:Knorr quinoline synthesis
101:keto/enol tautomerization
93:keto-enol tautomerization
3878:Pictet–Spengler reaction
3793:Einhorn–Brunner reaction
3758:Boger pyridine synthesis
3652:Oxo-Diels–Alder reaction
3567:Aza-Diels–Alder reaction
3464:Pictet–Spengler reaction
3364:Hofmann–Löffler reaction
3354:Hegedus indole synthesis
3324:Fischer indole synthesis
3199:Bartoli indole synthesis
3154:Willgerodt rearrangement
2984:McLafferty rearrangement
2894:Ferrier carbocyclization
2709:2,3-Wittig rearrangement
2699:1,2-Wittig rearrangement
2539:Parikh–Doering oxidation
2529:Oxygen rebound mechanism
2194:Adkins–Peterson reaction
2086:Yamaguchi esterification
2026:Hegedus indole synthesis
1991:Bartoli indole synthesis
1862:Bamford–Stevens reaction
1778:Weinreb ketone synthesis
1738:Stork enamine alkylation
1513:Knoevenagel condensation
1383:Ferrier carbocyclization
1273:Castro–Stephens coupling
899:Hammett acidity function
889:Free-energy relationship
834:Curtin–Hammett principle
819:Conformational isomerism
544:Conrad, M.; Limpach, L.
528:Conrad, M.; Limpach, L.
85:tetrahedral intermediate
21:Conrad–Limpach synthesis
3838:Knorr pyrrole synthesis
3773:Bucherer–Bergs reaction
3718:Allan–Robinson reaction
3697:Wagner-Jauregg reaction
3489:Ring-closing metathesis
3414:Larock indole synthesis
3394:Knorr pyrrole synthesis
3249:Bucherer–Bergs reaction
3114:Stieglitz rearrangement
3094:Skattebøl rearrangement
3064:Ring-closing metathesis
2924:Group transfer reaction
2889:Favorskii rearrangement
2829:Cornforth rearrangement
2759:Bamberger rearrangement
2664:Wolff–Kishner reduction
2484:Markó–Lam deoxygenation
2379:Fleming–Tamao oxidation
2374:Fischer–Tropsch process
2061:Oxymercuration reaction
2041:Knorr pyrrole synthesis
1867:Barton–Kellogg reaction
1773:Wagner-Jauregg reaction
1693:Ring-closing metathesis
1683:Reimer–Tiemann reaction
1673:Rauhut–Currier reaction
1588:Nef isocyanide reaction
1548:Malonic ester synthesis
1518:Knorr pyrrole synthesis
1453:High dilution principle
1388:Friedel–Crafts reaction
1323:Cross-coupling reaction
1248:Bucherer–Bergs reaction
1233:Blanc chloromethylation
1223:Blaise ketone synthesis
1198:Baylis–Hillman reaction
1193:Barton–Kellogg reaction
1168:Allan–Robinson reaction
1074:Woodward–Hoffmann rules
809:Charge-transfer complex
91:, which then undergoes
23:is the condensation of
3942:Condensation reactions
3803:Feist–Benary synthesis
3577:Bradsher cycloaddition
3547:4+4 Photocycloaddition
3504:Simmons–Smith reaction
3449:Paternò–Büchi reaction
3309:Feist–Benary synthesis
3299:Dieckmann condensation
3049:Pummerer rearrangement
3029:Oxy-Cope rearrangement
3004:Myers allene synthesis
2954:Jacobsen rearrangement
2869:Electrocyclic reaction
2844:Demjanov rearrangement
2799:Buchner ring expansion
2769:Beckmann rearrangement
2749:Aza-Cope rearrangement
2744:Arndt–Eistert reaction
2719:Alkyne zipper reaction
2639:Transfer hydrogenation
2614:Sharpless oxyamination
2589:Selenoxide elimination
2474:Lombardo methylenation
2399:Griesbaum coozonolysis
2309:Corey–Itsuno reduction
2284:Boyland–Sims oxidation
2224:Angeli–Rimini reaction
1872:Boord olefin synthesis
1816:Arndt–Eistert reaction
1808:Homologation reactions
1608:Nitro-Mannich reaction
1523:Kolbe–Schmitt reaction
1333:Cross-coupling partner
1253:Buchner ring expansion
1173:Arndt–Eistert reaction
939:Kinetic isotope effect
686:Rearrangement reaction
379:Heterocyclic Chemistry
71:
57:rearrangement reaction
3662:Pauson–Khand reaction
3499:Sharpless epoxidation
3454:Pechmann condensation
3334:Friedländer synthesis
3284:Davis–Beirut reaction
3139:Wallach rearrangement
3109:Stevens rearrangement
3044:Pinacol rearrangement
3024:Overman rearrangement
2939:Hofmann rearrangement
2934:Hayashi rearrangement
2899:Ferrier rearrangement
2854:Dimroth rearrangement
2839:Curtius rearrangement
2834:Criegee rearrangement
2814:Claisen rearrangement
2804:Carroll rearrangement
2739:Amadori rearrangement
2729:Allylic rearrangement
2609:Sharpless epoxidation
2344:Dess–Martin oxidation
2269:Bohn–Schmidt reaction
2129:Hofmann rearrangement
1932:Kauffmann olefination
1855:Olefination reactions
1793:Wurtz–Fittig reaction
1628:Palladium–NHC complex
1508:Kauffmann olefination
1463:Homologation reaction
1313:Corey–House synthesis
1293:Claisen rearrangement
1089:Yukawa–Tsuno equation
1049:Swain–Lupton equation
1029:Spherical aromaticity
964:Möbius–Hückel concept
749:Aromatic ring current
711:Substitution reaction
288:Ber. Dtsch. Chem. Ges
257:Ber. Dtsch. Chem. Ges
69:
31:) with β-ketoesters (
3868:Paal–Knorr synthesis
3738:Barton–Zard reaction
3682:Staudinger synthesis
3632:Ketene cycloaddition
3602:Diels–Alder reaction
3582:Cheletropic reaction
3562:Alkyne trimerisation
3444:Paal–Knorr synthesis
3409:Kulinkovich reaction
3384:Jacobsen epoxidation
3304:Diels–Alder reaction
3099:Smiles rearrangement
3089:Sigmatropic reaction
2974:Lossen rearrangement
2824:Corey–Fuchs reaction
2789:Boekelheide reaction
2784:Bergmann degradation
2714:Achmatowicz reaction
2499:Methionine sulfoxide
2299:Clemmensen reduction
2259:Bergmann degradation
2189:Acyloin condensation
2154:Strecker degradation
2109:Bergmann degradation
2076:Ullmann condensation
1942:Peterson olefination
1917:Hydrazone iodination
1897:Elimination reaction
1798:Zincke–Suhl reaction
1718:Sonogashira coupling
1678:Reformatsky reaction
1638:Peterson olefination
1603:Nierenstein reaction
1533:Kulinkovich reaction
1348:Diels–Alder reaction
1308:Corey–Fuchs reaction
1288:Claisen condensation
1158:Alkyne trimerisation
1133:Acyloin condensation
1099:Σ-bishomoaromaticity
1059:Thorpe–Ingold effect
671:Elimination reaction
471:Annu. Rev. Microbiol
3888:Prilezhaev reaction
3873:Pellizzari reaction
3552:(4+3) cycloaddition
3519:Van Leusen reaction
3494:Robinson annulation
3479:Pschorr cyclization
3474:Prilezhaev reaction
3204:Bergman cyclization
3159:Wolff rearrangement
3144:Weerman degradation
3034:Pericyclic reaction
3014:Neber rearrangement
2909:Fries rearrangement
2794:Brook rearrangement
2779:Bergman cyclization
2624:Staudinger reaction
2569:Rosenmund reduction
2559:Reductive amination
2524:Oppenauer oxidation
2314:Corey–Kim oxidation
2289:Cannizzaro reaction
2164:Weerman degradation
2139:Isosaccharinic acid
2051:Mukaiyama hydration
1907:Hofmann elimination
1892:Dehydrohalogenation
1877:Chugaev elimination
1698:Robinson annulation
1643:Pfitzinger reaction
1413:Gattermann reaction
1358:Wulff–Dötz reaction
1338:Dakin–West reaction
1263:Carbonyl allylation
1208:Bergman cyclization
994:Kennedy J. P. Orton
914:Hammond's postulate
884:Flippin–Lodge angle
854:Electromeric effect
779:Beta-silicon effect
764:Baker–Nathan effect
35:) to form 4-hydroxy
3637:McCormack reaction
3587:Conia-ene reaction
3419:Madelung synthesis
3209:Biginelli reaction
2999:Mumm rearrangement
2884:Favorskii reaction
2819:Cope rearrangement
2809:Chan rearrangement
2574:Rubottom oxidation
2504:Miyaura borylation
2469:Lipid peroxidation
2464:Lindgren oxidation
2444:Kornblum oxidation
2439:Kolbe electrolysis
2384:Fukuyama reduction
2294:Carbonyl reduction
2144:Marker degradation
2006:Diazonium compound
1996:Boudouard reaction
1975:Carbon-heteroatom
1902:Grieco elimination
1688:Rieche formylation
1633:Passerini reaction
1563:Meerwein arylation
1483:Hydroxymethylation
1378:Favorskii reaction
1278:Chan rearrangement
1213:Biginelli reaction
1138:Aldol condensation
984:2-Norbornyl cation
959:Möbius aromaticity
954:Markovnikov's rule
849:Effective molarity
794:Bürgi–Dunitz angle
784:Bicycloaromaticity
105:4-hydroxyquinoline
75:Reaction mechanism
72:
3929:
3928:
3925:
3924:
3921:
3920:
3913:Wohl–Aue reaction
3557:6+4 Cycloaddition
3374:Iodolactonization
2694:1,2-rearrangement
2659:Wohl–Aue reaction
2579:Sabatier reaction
2544:Pinnick oxidation
2509:Mozingo reduction
2454:Leuckart reaction
2409:Haloform reaction
2324:Criegee oxidation
2304:Collins oxidation
2254:Benkeser reaction
2249:Bechamp reduction
2219:Andrussow process
2204:Alcohol oxidation
2114:Edman degradation
2021:Haloform reaction
1970:
1969:
1957:Takai olefination
1922:Julia olefination
1748:Takai olefination
1623:Olefin metathesis
1498:Julia olefination
1423:Grignard reaction
1403:Fukuyama coupling
1318:Coupling reaction
1283:Chan–Lam coupling
1153:Alkyne metathesis
1148:Alkane metathesis
1004:Phosphaethynolate
909:George S. Hammond
869:Electronic effect
824:Conjugated system
706:Stereospecificity
701:Stereoselectivity
666:Addition reaction
655:organic reactions
450:10.1021/jm9509408
444:(26): 5176–5182.
53:addition reaction
16:Chemical reaction
3959:
3908:Wenker synthesis
3898:Stollé synthesis
3753:Bobbitt reaction
3723:Auwers synthesis
3667:Povarov reaction
3592:Cyclopropanation
3530:
3524:Wenker synthesis
3279:Darzens reaction
3229:Bobbitt reaction
3074:Schmidt reaction
2879:Enyne metathesis
2654:Whiting reaction
2649:Wharton reaction
2594:Shapiro reaction
2584:Sarett oxidation
2549:Prévost reaction
2359:Emde degradation
2169:Wohl degradation
2149:Ruff degradation
2119:Emde degradation
2016:Grignard reagent
1952:Shapiro reaction
1937:McMurry reaction
1804:
1768:Ullmann reaction
1733:Stollé synthesis
1723:Stetter reaction
1713:Shapiro reaction
1703:Sakurai reaction
1598:Negishi coupling
1578:Minisci reaction
1573:Michael reaction
1558:McMurry reaction
1553:Mannich reaction
1433:Hammick reaction
1428:Grignard reagent
1368:Enyne metathesis
1353:Doebner reaction
1343:Darzens reaction
1188:Barbier reaction
1178:Auwers synthesis
1105:
1079:Woodward's rules
1044:Superaromaticity
1034:Spiroaromaticity
934:Inductive effect
929:Hyperconjugation
904:Hammett equation
844:Edwards equation
696:Regioselectivity
647:
640:
633:
624:
618:Doebner reaction
589:Reitsema, R. H.
518:
508:
500:
494:
467:
461:
434:
428:
418:
395:
376:
370:
360:
343:(9): 1563–1569.
329:
314:
304:
303:
279:
273:
272:
252:
214:
114:
3967:
3966:
3962:
3961:
3960:
3958:
3957:
3956:
3932:
3931:
3930:
3917:
3818:Gewald reaction
3701:
3528:
3509:Skraup reaction
3344:Graham reaction
3339:Gewald reaction
3170:
3163:
2685:
2678:
2634:Swern oxidation
2619:Stahl oxidation
2564:Riley oxidation
2519:Omega oxidation
2479:Luche reduction
2429:Jones oxidation
2394:Glycol cleavage
2389:Ganem oxidation
2334:Davis oxidation
2329:Dakin oxidation
2264:Birch reduction
2214:Amide reduction
2180:
2173:
2134:Hooker reaction
2096:
2090:
1978:
1976:
1966:
1962:Wittig reaction
1850:
1846:Wittig reaction
1821:Hooker reaction
1802:
1783:Wittig reaction
1758:Thorpe reaction
1743:Suzuki reaction
1728:Stille reaction
1663:Quelet reaction
1538:Kumada coupling
1488:Ivanov reaction
1478:Hydrovinylation
1458:Hiyama coupling
1418:Glaser coupling
1228:Blaise reaction
1218:Bingel reaction
1203:Benary reaction
1120:
1118:
1112:
1103:
999:Passive binding
919:Homoaromaticity
769:Baldwin's rules
744:Antiaromaticity
739:Anomeric effect
715:
657:
651:
609:
586:, 113. (Review)
525:
523:Further reading
506:
501:
497:
468:
464:
435:
431:
409:(19): 13150–3.
396:
392:
373:
330:
326:
311:
308:
307:
281:
280:
276:
254:
253:
249:
244:
220:
193:kinetic product
177:
142:
138:
77:
17:
12:
11:
5:
3965:
3963:
3955:
3954:
3952:Name reactions
3949:
3944:
3934:
3933:
3927:
3926:
3923:
3922:
3919:
3918:
3916:
3915:
3910:
3905:
3900:
3895:
3890:
3885:
3880:
3875:
3870:
3865:
3860:
3855:
3850:
3845:
3840:
3835:
3830:
3825:
3823:Hantzsch ester
3820:
3815:
3810:
3805:
3800:
3795:
3790:
3785:
3780:
3775:
3770:
3765:
3760:
3755:
3750:
3745:
3740:
3735:
3733:Banert cascade
3730:
3725:
3720:
3715:
3709:
3707:
3703:
3702:
3700:
3699:
3694:
3689:
3684:
3679:
3674:
3672:Prato reaction
3669:
3664:
3659:
3654:
3649:
3644:
3639:
3634:
3629:
3624:
3619:
3614:
3609:
3604:
3599:
3594:
3589:
3584:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3538:
3536:
3527:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3471:
3466:
3461:
3456:
3451:
3446:
3441:
3436:
3431:
3426:
3421:
3416:
3411:
3406:
3401:
3396:
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3346:
3341:
3336:
3331:
3326:
3321:
3316:
3311:
3306:
3301:
3296:
3291:
3286:
3281:
3276:
3271:
3266:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3216:
3211:
3206:
3201:
3196:
3191:
3186:
3181:
3175:
3173:
3165:
3164:
3162:
3161:
3156:
3151:
3146:
3141:
3136:
3131:
3126:
3121:
3116:
3111:
3106:
3101:
3096:
3091:
3086:
3081:
3076:
3071:
3066:
3061:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2971:
2966:
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2926:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2786:
2781:
2776:
2771:
2766:
2764:Banert cascade
2761:
2756:
2751:
2746:
2741:
2736:
2731:
2726:
2721:
2716:
2711:
2706:
2701:
2696:
2690:
2688:
2684:Rearrangement
2680:
2679:
2677:
2676:
2674:Zinin reaction
2671:
2666:
2661:
2656:
2651:
2646:
2644:Wacker process
2641:
2636:
2631:
2626:
2621:
2616:
2611:
2606:
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2551:
2546:
2541:
2536:
2531:
2526:
2521:
2516:
2511:
2506:
2501:
2496:
2491:
2486:
2481:
2476:
2471:
2466:
2461:
2456:
2451:
2446:
2441:
2436:
2431:
2426:
2421:
2419:Hydrogenolysis
2416:
2411:
2406:
2401:
2396:
2391:
2386:
2381:
2376:
2371:
2369:Étard reaction
2366:
2361:
2356:
2351:
2346:
2341:
2336:
2331:
2326:
2321:
2316:
2311:
2306:
2301:
2296:
2291:
2286:
2281:
2276:
2274:Bosch reaction
2271:
2266:
2261:
2256:
2251:
2246:
2241:
2236:
2231:
2226:
2221:
2216:
2211:
2206:
2201:
2196:
2191:
2185:
2183:
2179:Organic redox
2175:
2174:
2172:
2171:
2166:
2161:
2156:
2151:
2146:
2141:
2136:
2131:
2126:
2121:
2116:
2111:
2106:
2100:
2098:
2092:
2091:
2089:
2088:
2083:
2078:
2073:
2068:
2063:
2058:
2053:
2048:
2043:
2038:
2033:
2028:
2023:
2018:
2013:
2011:Esterification
2008:
2003:
1998:
1993:
1988:
1982:
1980:
1972:
1971:
1968:
1967:
1965:
1964:
1959:
1954:
1949:
1944:
1939:
1934:
1929:
1924:
1919:
1914:
1909:
1904:
1899:
1894:
1889:
1884:
1879:
1874:
1869:
1864:
1858:
1856:
1852:
1851:
1849:
1848:
1843:
1838:
1833:
1828:
1823:
1818:
1812:
1810:
1801:
1800:
1795:
1790:
1788:Wurtz reaction
1785:
1780:
1775:
1770:
1765:
1760:
1755:
1750:
1745:
1740:
1735:
1730:
1725:
1720:
1715:
1710:
1705:
1700:
1695:
1690:
1685:
1680:
1675:
1670:
1665:
1660:
1658:Prins reaction
1655:
1650:
1645:
1640:
1635:
1630:
1625:
1620:
1615:
1610:
1605:
1600:
1595:
1590:
1585:
1580:
1575:
1570:
1565:
1560:
1555:
1550:
1545:
1540:
1535:
1530:
1525:
1520:
1515:
1510:
1505:
1500:
1495:
1490:
1485:
1480:
1475:
1473:Hydrocyanation
1470:
1465:
1460:
1455:
1450:
1445:
1443:Henry reaction
1440:
1435:
1430:
1425:
1420:
1415:
1410:
1405:
1400:
1395:
1390:
1385:
1380:
1375:
1370:
1365:
1360:
1355:
1350:
1345:
1340:
1335:
1330:
1325:
1320:
1315:
1310:
1305:
1300:
1295:
1290:
1285:
1280:
1275:
1270:
1265:
1260:
1255:
1250:
1245:
1240:
1235:
1230:
1225:
1220:
1215:
1210:
1205:
1200:
1195:
1190:
1185:
1180:
1175:
1170:
1165:
1160:
1155:
1150:
1145:
1143:Aldol reaction
1140:
1135:
1130:
1124:
1122:
1117:Carbon-carbon
1114:
1113:
1108:
1102:
1101:
1096:
1094:Zaitsev's rule
1091:
1086:
1081:
1076:
1071:
1066:
1061:
1056:
1051:
1046:
1041:
1039:Steric effects
1036:
1031:
1026:
1021:
1016:
1011:
1006:
1001:
996:
991:
986:
981:
976:
971:
966:
961:
956:
951:
946:
941:
936:
931:
926:
921:
916:
911:
906:
901:
896:
891:
886:
881:
876:
871:
866:
861:
856:
851:
846:
841:
836:
831:
826:
821:
816:
811:
806:
801:
796:
791:
786:
781:
776:
771:
766:
761:
756:
751:
746:
741:
736:
731:
726:
720:
717:
716:
714:
713:
708:
703:
698:
693:
691:Redox reaction
688:
683:
678:
676:Polymerization
673:
668:
662:
659:
658:
652:
650:
649:
642:
635:
627:
621:
620:
615:
608:
605:
604:
603:
602:, 43. (Review)
587:
573:Manske, R. H.
571:
558:
542:
524:
521:
520:
519:
495:
462:
429:
390:
371:
324:
306:
305:
294:(1): 948–959.
274:
263:(1): 944–948.
246:
245:
243:
240:
219:
216:
176:
173:
140:
136:
76:
73:
15:
13:
10:
9:
6:
4:
3:
2:
3964:
3953:
3950:
3948:
3945:
3943:
3940:
3939:
3937:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3896:
3894:
3891:
3889:
3886:
3884:
3881:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3833:Herz reaction
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3814:
3811:
3809:
3806:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3779:
3776:
3774:
3771:
3769:
3766:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3710:
3708:
3704:
3698:
3695:
3693:
3690:
3688:
3685:
3683:
3680:
3678:
3675:
3673:
3670:
3668:
3665:
3663:
3660:
3658:
3655:
3653:
3650:
3648:
3645:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3623:
3620:
3618:
3615:
3613:
3610:
3608:
3605:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3545:
3543:
3540:
3539:
3537:
3535:
3534:Cycloaddition
3531:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3462:
3460:
3457:
3455:
3452:
3450:
3447:
3445:
3442:
3440:
3437:
3435:
3432:
3430:
3427:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3379:Isay reaction
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3320:
3317:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3274:Cycloaddition
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3217:
3215:
3212:
3210:
3207:
3205:
3202:
3200:
3197:
3195:
3192:
3190:
3187:
3185:
3182:
3180:
3177:
3176:
3174:
3172:
3169:Ring forming
3166:
3160:
3157:
3155:
3152:
3150:
3147:
3145:
3142:
3140:
3137:
3135:
3132:
3130:
3127:
3125:
3122:
3120:
3117:
3115:
3112:
3110:
3107:
3105:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3069:Rupe reaction
3067:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2767:
2765:
2762:
2760:
2757:
2755:
2752:
2750:
2747:
2745:
2742:
2740:
2737:
2735:
2732:
2730:
2727:
2725:
2722:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2691:
2689:
2687:
2681:
2675:
2672:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2622:
2620:
2617:
2615:
2612:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2530:
2527:
2525:
2522:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2500:
2497:
2495:
2492:
2490:
2487:
2485:
2482:
2480:
2477:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2459:Ley oxidation
2457:
2455:
2452:
2450:
2447:
2445:
2442:
2440:
2437:
2435:
2432:
2430:
2427:
2425:
2424:Hydroxylation
2422:
2420:
2417:
2415:
2414:Hydrogenation
2412:
2410:
2407:
2405:
2402:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2380:
2377:
2375:
2372:
2370:
2367:
2365:
2362:
2360:
2357:
2355:
2352:
2350:
2349:DNA oxidation
2347:
2345:
2342:
2340:
2339:Deoxygenation
2337:
2335:
2332:
2330:
2327:
2325:
2322:
2320:
2317:
2315:
2312:
2310:
2307:
2305:
2302:
2300:
2297:
2295:
2292:
2290:
2287:
2285:
2282:
2280:
2277:
2275:
2272:
2270:
2267:
2265:
2262:
2260:
2257:
2255:
2252:
2250:
2247:
2245:
2242:
2240:
2237:
2235:
2232:
2230:
2229:Aromatization
2227:
2225:
2222:
2220:
2217:
2215:
2212:
2210:
2207:
2205:
2202:
2200:
2197:
2195:
2192:
2190:
2187:
2186:
2184:
2182:
2176:
2170:
2167:
2165:
2162:
2160:
2157:
2155:
2152:
2150:
2147:
2145:
2142:
2140:
2137:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2101:
2099:
2093:
2087:
2084:
2082:
2079:
2077:
2074:
2072:
2069:
2067:
2066:Reed reaction
2064:
2062:
2059:
2057:
2054:
2052:
2049:
2047:
2044:
2042:
2039:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2019:
2017:
2014:
2012:
2009:
2007:
2004:
2002:
1999:
1997:
1994:
1992:
1989:
1987:
1984:
1983:
1981:
1977:bond forming
1973:
1963:
1960:
1958:
1955:
1953:
1950:
1948:
1945:
1943:
1940:
1938:
1935:
1933:
1930:
1928:
1925:
1923:
1920:
1918:
1915:
1913:
1910:
1908:
1905:
1903:
1900:
1898:
1895:
1893:
1890:
1888:
1885:
1883:
1882:Cope reaction
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1860:
1859:
1857:
1853:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1813:
1811:
1809:
1805:
1799:
1796:
1794:
1791:
1789:
1786:
1784:
1781:
1779:
1776:
1774:
1771:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1736:
1734:
1731:
1729:
1726:
1724:
1721:
1719:
1716:
1714:
1711:
1709:
1706:
1704:
1701:
1699:
1696:
1694:
1691:
1689:
1686:
1684:
1681:
1679:
1676:
1674:
1671:
1669:
1666:
1664:
1661:
1659:
1656:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1593:Nef synthesis
1591:
1589:
1586:
1584:
1581:
1579:
1576:
1574:
1571:
1569:
1568:Methylenation
1566:
1564:
1561:
1559:
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1471:
1469:
1466:
1464:
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1444:
1441:
1439:
1438:Heck reaction
1436:
1434:
1431:
1429:
1426:
1424:
1421:
1419:
1416:
1414:
1411:
1409:
1406:
1404:
1401:
1399:
1396:
1394:
1391:
1389:
1386:
1384:
1381:
1379:
1376:
1374:
1371:
1369:
1366:
1364:
1361:
1359:
1356:
1354:
1351:
1349:
1346:
1344:
1341:
1339:
1336:
1334:
1331:
1329:
1326:
1324:
1321:
1319:
1316:
1314:
1311:
1309:
1306:
1304:
1301:
1299:
1296:
1294:
1291:
1289:
1286:
1284:
1281:
1279:
1276:
1274:
1271:
1269:
1266:
1264:
1261:
1259:
1256:
1254:
1251:
1249:
1246:
1244:
1241:
1239:
1236:
1234:
1231:
1229:
1226:
1224:
1221:
1219:
1216:
1214:
1211:
1209:
1206:
1204:
1201:
1199:
1196:
1194:
1191:
1189:
1186:
1184:
1181:
1179:
1176:
1174:
1171:
1169:
1166:
1164:
1161:
1159:
1156:
1154:
1151:
1149:
1146:
1144:
1141:
1139:
1136:
1134:
1131:
1129:
1126:
1125:
1123:
1119:bond forming
1115:
1111:
1106:
1100:
1097:
1095:
1092:
1090:
1087:
1085:
1084:Y-aromaticity
1082:
1080:
1077:
1075:
1072:
1070:
1069:Walsh diagram
1067:
1065:
1062:
1060:
1057:
1055:
1054:Taft equation
1052:
1050:
1047:
1045:
1042:
1040:
1037:
1035:
1032:
1030:
1027:
1025:
1024:Σ-aromaticity
1022:
1020:
1017:
1015:
1012:
1010:
1007:
1005:
1002:
1000:
997:
995:
992:
990:
987:
985:
982:
980:
977:
975:
972:
970:
967:
965:
962:
960:
957:
955:
952:
950:
949:Marcus theory
947:
945:
942:
940:
937:
935:
932:
930:
927:
925:
924:Hückel's rule
922:
920:
917:
915:
912:
910:
907:
905:
902:
900:
897:
895:
892:
890:
887:
885:
882:
880:
879:Evelyn effect
877:
875:
872:
870:
867:
865:
862:
860:
859:Electron-rich
857:
855:
852:
850:
847:
845:
842:
840:
837:
835:
832:
830:
827:
825:
822:
820:
817:
815:
812:
810:
807:
805:
802:
800:
797:
795:
792:
790:
787:
785:
782:
780:
777:
775:
774:Bema Hapothle
772:
770:
767:
765:
762:
760:
757:
755:
752:
750:
747:
745:
742:
740:
737:
735:
732:
730:
727:
725:
722:
721:
718:
712:
709:
707:
704:
702:
699:
697:
694:
692:
689:
687:
684:
682:
679:
677:
674:
672:
669:
667:
664:
663:
660:
656:
648:
643:
641:
636:
634:
629:
628:
625:
619:
616:
614:
611:
610:
606:
601:
597:
594:
593:
588:
585:
581:
578:
577:
572:
569:
565:
564:
559:
556:
552:
549:
548:
543:
540:
536:
533:
532:
527:
526:
522:
517:(6): 841–845.
516:
512:
505:
499:
496:
492:
488:
484:
480:
476:
472:
466:
463:
459:
455:
451:
447:
443:
439:
433:
430:
426:
422:
417:
412:
408:
404:
400:
394:
391:
388:
384:
380:
375:
372:
368:
364:
359:
354:
350:
346:
342:
338:
337:Synth. Commun
334:
328:
325:
322:
318:
313:
310:
309:
301:
297:
293:
289:
285:
278:
275:
270:
266:
262:
258:
251:
248:
241:
239:
237:
233:
229:
224:
217:
215:
213:
208:
206:
202:
198:
194:
190:
186:
182:
174:
172:
170:
166:
162:
158:
157:the enol form
154:
150:
145:
143:
132:
127:
125:
120:
115:
113:
108:
106:
102:
98:
94:
90:
86:
82:
74:
68:
64:
62:
58:
55:as well as a
54:
50:
46:
42:
38:
34:
30:
26:
22:
2874:Ene reaction
2234:Autoxidation
2095:Degradation
1986:Azo coupling
1763:Ugi reaction
1363:Ene reaction
1163:Alkynylation
1014:Polyfluorene
1009:Polar effect
874:Electrophile
789:Bredt's rule
759:Baird's rule
729:Alpha effect
599:
595:
590:
583:
579:
574:
561:
554:
550:
545:
538:
534:
529:
514:
510:
498:
474:
470:
465:
441:
438:J. Med. Chem
437:
432:
406:
402:
393:
378:
374:
340:
336:
327:
312:
291:
287:
277:
260:
256:
250:
235:
231:
227:
225:
221:
218:Applications
209:
197:Ludwig Knorr
178:
168:
146:
128:
116:
109:
78:
48:
40:
32:
28:
20:
18:
1373:Ethenolysis
1019:Ring strain
989:Nucleophile
814:Clar's rule
754:Aromaticity
563:Org. Synth.
477:: 427–454.
403:J Biol Chem
124:mineral oil
89:Schiff base
45:Schiff base
3936:Categories
3657:Ozonolysis
3184:Annulation
2534:Ozonolysis
653:Topics in
592:Chem. Rev.
576:Chem. Rev.
387:0854046526
321:3642010520
242:References
149:quinolines
119:annulation
103:to form a
95:before an
61:Max Conrad
37:quinolines
3171:reactions
2686:reactions
2181:reactions
2097:reactions
1979:reactions
1121:reactions
165:keto form
161:quinolone
1064:Vinylogy
734:Annulene
681:Reagents
607:See also
367:20046955
43:) via a
25:anilines
724:A value
568:Article
557:, 2990.
491:4901983
458:8978845
425:1320012
358:2744084
181:aniline
81:aniline
541:, 944.
489:
456:
423:
385:
365:
355:
319:
236:et al.
232:et al.
228:et al.
507:(pdf)
189:ester
596:1948
580:1942
551:1891
547:Ber.
535:1887
531:Ber.
487:PMID
454:PMID
421:PMID
383:ISBN
363:PMID
317:ISBN
185:keto
19:The
479:doi
446:doi
411:doi
407:267
353:PMC
345:doi
296:doi
265:doi
133:or
131:HCl
3938::
600:43
598:,
584:30
582:,
555:24
553:,
539:20
537:,
515:25
513:.
509:.
485:.
475:23
473:.
452:.
442:39
440:.
419:.
405:.
401:.
361:.
351:.
341:39
339:.
335:.
292:20
290:.
286:.
261:20
259:.
144:.
139:SO
646:e
639:t
632:v
570:)
493:.
481::
460:.
448::
427:.
413::
389:.
369:.
347::
323:.
302:.
298::
271:.
267::
163:(
141:4
137:2
135:H
49:3
47:(
41:4
39:(
33:2
29:1
27:(
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
