362:
313:
328:
377:
347:
294:
280:. Sultams are prepared analogously to other sulfonamides, allowing for the fact that sulfonic acids are deprotonated by amines. They are often prepared by one-pot oxidation of disulfides or thiols linked to amines. An alternative synthesis of sultams involves initial preparation of a linear sulfonamide, followed by intramolecular C-C bond formation (i.e. cyclization), a strategy that was used in the synthesis of a sultam-based deep-blue emitter for
49:
361:
312:
250:
Sulfonamides undergo a variety of acid-base reactions. The N-H bond can be deprotonated. The alkylsulfonamides can be deprotonated at carbon. Arylsulfonamides undergo
517:
293:
550:
376:
239:
is typically added to absorb the HCl that is generated. Illustrative is the synthesis of sulfonylmethylamide. The reaction of primary and secondary amines with
876:
116:; for this reason, the formation of a sulfonamide is a classic method to convert an amine into a crystalline derivative which can be identified by its
1795:
650:
Rassadin, V.; Grosheva, D.; Tomashevskii, A. Sokolov, V. "Methods of Sultam
Synthesis" Chemistry of Heterocyclic Compounds 2013, Vol. 49, p39-65. 27.
1800:
756:
James, Thomas; van
Gemmeren, Manuel; List, Benjamin (2015). "Development and Applications of Disulfonimides in Enantioselective Organocatalysis".
327:
346:
635:
431:
534:
575:
869:
1699:
618:
Tanaka, Kazuhiko (1991). "Sulfonic Acids, Esters, Amides and
Halides as Synthons". In Saul Patai, Zvi Rappoport (ed.).
668:
Virk, Tarunpreet Singh; Ilawe, Niranjan V.; Zhang, Guoxian; Yu, Craig P.; Wong, Bryan M.; Chan, Julian M. W. (2016).
1823:
1272:
862:
544:
473:
with two sulfonyl groups flanking an amine. As with sulfinamides, this class of compounds is used as catalysts in
670:"Sultam-Based Hetero[5]helicene: Synthesis, Structure, and Crystallization-Induced Emission Enhancement"
1309:
240:
791:
Treskow, M.; Neudörfl, J.; Giernoth, R. (2009). "BINBAM – A New Motif for Strong and Chiral Brønsted Acids".
1782:
1682:
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416:
201:
Sulfonamides can be prepared in the laboratory in many ways. The classic approach entails the reaction of
190:
35:
1828:
1789:
1677:
303:
193:, a derivative or variation of sulfanilamide. The first sulfonamide was discovered in Germany in 1932.
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76:
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The antibiotic paradox : how the misuse of antibiotics destroys their curative powers
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910:
147:, where each R is some organic group; for example, "methanesulfonamide" (where R =
72:
1706:
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1548:
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1421:
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1404:
969:
964:
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273:
113:
818:
García-García, P.; Lay, F.; García-García, P.; Rabalakos, C.; List, B. (2009).
741:
729:
717:
112:. Because of the rigidity of the functional group, sulfonamides are typically
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1339:
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1138:
1086:
655:
337:
109:
685:
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526:
419:, p-toluenesulfinamide and 2,4,6-trimethylbenzenesulfinamide are relevant to
1629:
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1508:
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1324:
1299:
1108:
627:
496:
299:
277:
42:
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819:
804:
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703:
515:
Actor, P.; Chow, A. W.; Dutko, F. J.; McKinlay, M. A. "Chemotherapeutics".
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236:
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are cyclic sulfonamides. Bioactive sultams include the antiinflammatory
48:
1599:
1523:
1374:
1369:
1334:
1319:
1314:
1284:
1267:
1091:
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de Boer, Th. J.; Backer, H. J. (1954). "p-Toluenesulfonylnitrosamide".
435:
148:
1687:
1619:
1463:
1172:
1165:
1059:
1040:
1029:
1013:
959:
716:
Organic
Syntheses, Coll. Vol. 10, p.47 (2004); Vol. 77, p.50 (2000).
412:
263:
854:
370:
is a drug that features both acyclic and cyclic sulfonamide groups.
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1538:
1471:
1329:
1294:
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1210:
1177:
1081:
905:
570:(2 ed.). Cambridge, Massachusetts: Perseus Publ. p. 51.
206:
98:
996:
858:
820:"A Powerful Chiral Counteranion Motif for Asymmetric Catalysis"
321:, a compound that foreshadowed the development of sulfa drugs
622:. PATAI'S Chemistry of Functional Groups. pp. 401–452.
189:, the term "sulfonamide" is sometimes used as a synonym for
34:
For the medical use of chemicals within this group, see
247:, a method for detecting primary and secondary amines.
120:. Many important drugs contain the sulfonamide group.
170:. Any sulfonamide can be considered as derived from a
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1253:
1230:
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1027:
892:
302:, a cyclic sulfonamide that was one of the first
262:"Sultam" redirects here. Not to be confused with
131:that contains this group. The general formula is
518:Ullmann's Encyclopedia of Industrial Chemistry
870:
355:is a sultam used as an antiinflammatory drug.
8:
549:: CS1 maint: multiple names: authors list (
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85:
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27:Organosulfur compounds containing –S(=O)
507:
286:
542:
52:The structure of the sulfonamide group
108:). Relatively speaking this group is
7:
432:Bis(trifluoromethanesulfonyl)aniline
25:
375:
360:
345:
326:
311:
292:
740:Org. Synth. 2006, 83, 131-140
728:Org. Synth. 2007, 84, 129-138
1:
770:10.1021/acs.chemrev.5b00128
288:Sulfonamide-based compounds
1845:
403:(R(S=O)NHR) are amides of
261:
40:
33:
1772:
656:10.1007/s10593-013-1231-3
686:10.1021/acsomega.6b00335
605:10.15227/orgsyn.034.0096
564:Levy, Stuart B. (2002).
527:10.1002/14356007.a06_173
241:benzenesulfonyl chloride
41:Not to be confused with
1783:chemical classification
628:10.1002/0470034394.ch11
521:. Weinheim: Wiley-VCH.
276:and the anticonvulsant
197:Synthesis and reactions
182:) with an amine group.
31:–N< functional group
18:Sulfonamide (chemistry)
837:10.1002/anie.200901768
805:10.1002/ejoc.200900548
487:Sulfonamide (medicine)
417:tert-butanesulfinamide
389:in organic synthesis.
385:is a sultam used as a
53:
36:Sulfonamide (medicine)
1790:chemical nomenclature
415:sulfinamides such as
304:artificial sweeteners
51:
824:Angew. Chem. Int. Ed
421:asymmetric synthesis
243:is the basis of the
1246:not C, H or O)
434:is a source of the
368:Hydrochlorothiazide
282:organic electronics
89:. It consists of a
1688:Hypervalent iodine
203:sulfonyl chlorides
97:) connected to an
54:
1824:Functional groups
1811:
1810:
1749:Sulfenyl chloride
1727:
1726:
1226:
1225:
1045:(only C, H and O)
886:Functional groups
830:(24): 4363–4366.
799:(22): 3693–3697.
793:Eur. J. Org. Chem
764:(17): 9388–9409.
637:978-0-470-03439-2
545:cite encyclopedia
336:is a widely used
245:Hinsberg reaction
129:chemical compound
58:organic chemistry
16:(Redirected from
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680:(6): 1336–1342.
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475:enantioselective
472:
461:are of the type
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451:
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407:(R(S=O)OH) (see
387:chiral auxiliary
379:
364:
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334:Sulfamethoxazole
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252:ortho-lithiation
231:
181:
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127:(compound) is a
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65:functional group
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1678:Trichloromethyl
1673:Trifluoromethyl
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1458:
1427:Phosphine oxide
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1767:
1766:
1764:Sulfinylamines
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1756:
1751:
1746:
1744:Phosphoramides
1741:
1739:Isothiocyanate
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1615:Selenenic acid
1612:
1610:Seleninic acid
1607:
1605:Selenonic acid
1602:
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1398:Phosphodiester
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1244:(one element,
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1121:Methylenedioxy
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898:(only C and H)
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536:978-3527306732
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459:disulfonimides
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427:Disulfonimides
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405:sulfinic acids
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67:(also spelled
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1529:Sulfonic acid
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1519:Sulfinic acid
1517:
1515:
1514:Thiosulfonate
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1510:
1507:
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1504:Thiosulfinate
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1499:Sulfenic acid
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1454:Phosphaallene
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1449:Phosphaalkyne
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1444:Phosphaalkene
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1128:
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1119:
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1116:Ethylenedioxy
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577:9780738204406
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492:Sulfamic acid
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319:Sulfanilamide
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309:
305:
301:
295:
290:
287:
285:
283:
279:
275:
271:
265:
257:
255:
253:
248:
246:
242:
238:
212:
211:
210:
208:
204:
196:
194:
192:
188:
183:
177:
173:
172:sulfonic acid
154:
150:
130:
126:
121:
119:
118:melting point
115:
111:
100:
92:
78:
74:
70:
66:
63:
59:
50:
44:
37:
19:
1829:Sulfonamides
1788:
1781:
1753:
1695:Vinyl halide
1652:
1582:Borinic acid
1577:Boronic acid
1554:Thioxanthate
894:Hydrocarbons
827:
823:
813:
796:
792:
786:
761:
757:
736:
724:
712:
677:
673:
663:
646:
619:
613:
596:
592:
586:
566:
559:
516:
510:
458:
456:
430:
401:sulfinamides
399:The related
398:
395:Sulfinamides
269:
268:
249:
234:
200:
184:
151:, R' = R" =
124:
122:
73:organosulfur
69:sulphonamide
68:
61:
55:
1759:Thiocyanate
1754:Sulfonamide
1719:Perchlorate
1707:Acyl halide
1668:Fluoroethyl
1549:Thionoester
1437:Phosphonium
1422:Phosphinate
1417:Phosphonous
1405:Phosphonate
1104:Hydroperoxy
926:Cyclopropyl
477:synthesis.
467:−N(H)−S(=O)
353:Ampiroxicam
274:ampiroxicam
125:sulfonamide
114:crystalline
62:sulfonamide
1818:Categories
1663:Haloalkane
1534:Thioketone
1489:Persulfide
1385:Phosphorus
1350:Isocyanate
1340:Isonitrile
1241:or oxygen
1239:hydrogen,
1235:not being
1216:Orthoester
1109:Dioxiranes
1087:Enol ether
975:1-Propenyl
593:Org. Synth
503:References
338:antibiotic
306:discovered
222:NH → RSO
191:sulfa drug
110:unreactive
1796:inorganic
1630:Tellurium
1544:Thioester
1509:Sulfoxide
1494:Disulfide
1482:Sulfonium
1432:Phosphine
1410:Phosphite
1393:Phosphate
1325:Carbamate
1300:Hydrazone
1233:element,
1231:Only one
1204:Anhydride
943:Methylene
758:Chem. Rev
674:ACS Omega
497:Sulfamide
454:) group.
300:Saccharin
278:sulthiame
77:structure
43:Sulfamide
1777:See also
1712:Chloride
1638:Tellurol
1592:Selenium
1559:Xanthate
1273:Ammonium
1255:Nitrogen
1237:carbon,
1194:Carboxyl
1161:Aldehyde
1149:Acryloyl
1131:carbonyl
1035:hydrogen
990:Cumulene
846:19437518
778:26147232
704:31457199
481:See also
409:sulfinyl
237:pyridine
205:with an
187:medicine
176:hydroxyl
153:hydrogen
91:sulfonyl
71:) is an
1801:organic
1600:Selenol
1524:Sulfone
1477:Sulfide
1375:NONOate
1370:Nitroso
1360:Nitrite
1355:Nitrate
1345:Cyanate
1335:Nitrile
1320:Amidine
1315:Imidate
1285:Nitrene
1280:Hydrazo
1268:Enamine
1199:Acetoxy
1187:carboxy
1154:Benzoyl
1092:Epoxide
1075:Methoxy
1065:Alcohol
1019:Carbene
953:Methine
695:6640820
463:R−S(=O)
436:triflyl
270:Sultams
258:Sultams
218:Cl + R'
178:group (
149:methane
141:R−S(=O)
101:group (
93:group (
80:R−S(=O)
1700:Iodide
1620:Selone
1464:Sulfur
1173:Ketone
1166:Ketene
1144:Acetyl
1099:Peroxy
1070:Alkoxy
1060:Acetal
1041:oxygen
1030:carbon
1014:Alkyne
1007:Benzyl
1002:Phenyl
985:Allene
980:Crotyl
960:Alkene
948:Bridge
936:Pentyl
921:Propyl
911:Methyl
844:
776:
702:
692:
634:
599:: 96.
574:
533:
413:Chiral
264:Sultan
145:−NR'R"
60:, the
1732:Other
1569:Boron
1539:Thial
1472:Thiol
1365:Nitro
1330:Imide
1310:Amide
1295:Oxime
1290:Imine
1263:Amine
1211:Ester
1178:Ynone
1082:Ether
1053:R-O-R
1028:Only
970:Allyl
965:Vinyl
931:Butyl
916:Ethyl
906:Alkyl
230:+ HCl
207:amine
155:) is
137:NR'R"
99:amine
95:O=S=O
1654:Halo
1139:Acyl
1039:and
997:Aryl
842:PMID
797:2009
774:PMID
742:Link
730:Link
718:Link
700:PMID
632:ISBN
572:ISBN
551:link
531:ISBN
457:The
209:.
133:R−SO
1305:Azo
832:doi
801:doi
766:doi
762:115
690:PMC
682:doi
652:doi
624:doi
601:doi
523:doi
471:−R’
411:).
226:NR'
214:RSO
185:In
180:−OH
139:or
103:−NH
84:−NR
56:In
1820::
1037:,
1032:,
840:.
828:48
826:.
822:.
795:.
772:.
760:.
748:^
698:.
688:.
676:.
672:.
630:.
597:34
595:.
547:}}
543:{{
529:.
444:SO
440:CF
423:.
284:.
254:.
165:NH
161:SO
157:CH
123:A
878:e
871:t
864:v
848:.
834::
807:.
803::
780:.
768::
706:.
684::
678:1
658:.
654::
640:.
626::
607:.
603::
580:.
553:)
539:.
525::
469:2
465:2
450:2
447:+
442:3
438:(
340:.
266:.
228:2
224:2
220:2
216:2
167:2
163:2
159:3
143:2
135:2
105:2
86:2
82:2
45:.
38:.
29:2
20:)
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