2327:
2421:
2334:
2240:
2514:
2341:
2449:
40:
2261:
2168:
2414:
2362:
2161:
2442:
2507:
2435:
2521:
2493:
2348:
2196:
2175:
2428:
2268:
2607:
2528:
2600:
2275:
2189:
2182:
2686:
2665:
2586:
2679:
2672:
2658:
2593:
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2254:
2651:
2355:
2500:
48:
2247:
117:
The study of organic heterocyclic chemistry focuses especially on organic unsaturated derivatives, and the preponderance of work and applications involves unstrained organic 5- and 6-membered rings. Included are
2917:
Edon Vitaku, David T. Smith, Jon T. Njardarson (2014). "Analysis of the
Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals".
154:, respectively. The fusion of two benzene rings gives rise to a third large family of organic compounds. Analogs of the previously mentioned heterocycles for this third family of compounds are
173:
Heterocyclic organic compounds can be usefully classified based on their electronic structure. The saturated organic heterocycles behave like the acyclic derivatives. Thus,
2965:
234:
2952:
3184:
1796:
In a 7-membered ring, the heteroatom must be able to provide an empty π-orbital (e.g. boron) for "normal" aromatic stabilization to be available; otherwise,
2703:
or heterocyclic, have a variety of common and systematic names. For example, with the benzo-fused unsaturated nitrogen heterocycles, pyrrole provides
233:. In comparison with organic heterocycles, which have numerous commercial applications, inorganic ring systems are mainly of theoretical interest.
3010:
3138:
2326:
3077:
3051:
2877:
3213:
31:
189:, with modified steric profiles. Therefore, the study of organic heterocyclic chemistry focuses on organic unsaturated rings.
1774:
101:
and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US
2825:
Heterocyclic compounds are pervasive in many areas of life sciences and technology. Many drugs are heterocyclic compounds.
3181:
262:
238:
2420:
2239:
2333:
1615:
2513:
2340:
222:
3193:
2723:
is the preferred name. Likewise, the compounds with two benzene rings fused to the central heterocycle are
2642:
2448:
2069:
3176:
3000:
2260:
2167:
2946:
210:
2413:
3112:
1013:
2872:
Thomas L. Gilchrist "Heterocyclic
Chemistry" 3rd ed. Addison Wesley: Essex, England, 1997. 414 pp.
2805:
2361:
2160:
1323:
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2527:
1462:
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1395:
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577:
2678:
2671:
2657:
2650:
2592:
2578:
2571:
2520:
2492:
2347:
2274:
1480:
812:
2801:
isolates chlorophyll derivatives from crude oil, explaining the biological origin of petroleum.
2499:
2441:
2427:
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2188:
2181:
1907:
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1128:
962:
530:
3146:
3006:
2934:
2873:
2752:
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2563:
2548:
2267:
2064:
1991:
1986:
1573:
1413:
1390:
1269:
1238:
79:
2622:
2617:
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2543:
2049:
2034:
1976:
1971:
597:
582:
3120:
2979:
2926:
2899:
2798:
2736:
159:
138:. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are
71:
3025:
2354:
3188:
2853:
2751:
The history of heterocyclic chemistry began in the 1800s, in step with the development of
2732:
1797:
1467:
957:
953:
775:
178:
67:
3103:
Campaigne, E. (1986). "Adrien Albert and the rationalization of heterocyclic chemistry".
3116:
2699:
Heterocyclic rings systems that are formally derived by fusion with other rings, either
3197:
1550:
1400:
347:
143:
2739:
are a tricyclic phosphorus-containing heterocyclic system derived from the carbocycle
39:
17:
3207:
2778:
1279:
985:
913:
90:
2975:
1785:
is a six-membered ring with three nitrogen heteroatoms and three boron heteroatoms.
2716:
1446:
1009:
919:
865:
167:
135:
3171:
267:
Some of the names refer to classes of compounds rather than individual compounds.
2996:
2970:
2834:
2720:
2286:
1725:
1378:
1373:
1116:
1027:
981:
931:
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439:
424:
372:
367:
284:
2813:
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2700:
2373:
2003:
1924:
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1588:
1533:
1329:
1308:
1140:
1104:
1049:
1022:
942:
790:
658:
607:
386:
174:
151:
2974:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
2983:
2903:
2764:
2740:
2724:
2712:
2708:
2404:
2317:
2206:
2127:
1912:
1759:
1710:
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1517:
1457:
1434:
1287:
1184:
1152:
1037:
999:
994:
926:
858:
850:
800:
635:
630:
heteroatoms, at least one of which is nitrogen, are collectively called the
592:
495:
452:
429:
328:
163:
139:
123:
98:
2938:
2770:
2728:
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1385:
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1317:
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1054:
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807:
746:
686:
612:
540:
392:
382:
315:
198:
155:
119:
106:
51:
2856:
2794:, allowing synthetic chemistry to displace a large agricultural industry
134:. Another large class of organic heterocycles refers to those fused to
2890:
Rees, Charles W. (1992). "Polysulfur-Nitrogen
Heterocyclic Chemistry".
2784:
2760:
2637:
2632:
2553:
2538:
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2474:
2464:
2459:
2303:
2292:
2211:
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2132:
2054:
2039:
1961:
1956:
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1855:
1845:
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990:
824:
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724:
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510:
357:
351:
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271:
127:
94:
3124:
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2704:
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2103:
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1418:
1257:
839:
832:
769:
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709:
643:
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251:
186:
182:
147:
47:
2397:
2379:
2310:
2226:
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1356:
1346:
1340:
1264:
782:
731:
515:
500:
258:
131:
46:
38:
3002:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
2808:
are described, highlighting the role of heterocyclic compounds (
3182:
List of known and probable carcinogens, American Cancer
Society
1475:
872:
102:
27:
Molecule with one or more rings composed of different elements
657:
or more heteroatoms also exists. One example is the class of
82:
dealing with the synthesis, properties, and applications of
661:, which contain two sulfur atoms and one nitrogen atom.
287:, 3-membered heterocyclic rings are well characterized.
3139:"IPEXL.com Multilingual Patent Search, Patent Ranking"
2711:
depending on the orientation. The pyridine analog is
89:
Examples of heterocyclic compounds include all of the
43:
Structures and names of common heterocyclic compounds
3194:
List of known carcinogens by the State of
California
197:Some heterocycles contain no carbon. Examples are
653:A large group of 5-membered ring compounds with
250:"Heteroatoms" are atoms in the ring other than
3005:(6th ed.), New York: Wiley-Interscience,
8:
2951:: CS1 maint: multiple names: authors list (
2868:
2866:
3177:Heterocyclic amines in cooked meat, US CDC
2787:("fiery oil") by dry distillation of bones
626:The 5-membered ring compounds containing
70:that has atoms of at least two different
2081:
2016:
1938:
1882:
1803:
1732:
1683:
1622:
1492:
1198:
1061:
904:Unsaturated (and partially unsaturated)
887:
664:
552:
470:
399:
290:
30:For other uses of "ring structure", see
2846:
2735:are the fusion of two thiophene rings.
1777:with six nitrogen heteroatoms would be
1769:Six-membered rings with six heteroatoms
2944:
7:
3172:Hantzsch-Widman nomenclature, IUPAC
2078:Images of rings with one heteroatom
241:for naming heterocyclic compounds.
2971:Compendium of Chemical Terminology
646:and a nitrogen atom in the ring.
25:
2892:Journal of Heterocyclic Chemistry
2755:. Some noteworthy developments:
2747:History of heterocyclic chemistry
257:Names in italics are retained by
2684:
2677:
2670:
2663:
2656:
2649:
2605:
2598:
2591:
2584:
2577:
2570:
2526:
2519:
2512:
2505:
2498:
2491:
2447:
2440:
2433:
2426:
2419:
2412:
2360:
2353:
2346:
2339:
2332:
2325:
2273:
2266:
2259:
2252:
2245:
2238:
2194:
2187:
2180:
2173:
2166:
2159:
270:Also no attempt is made to list
2790:1906: Friedlander synthesizes
1775:hypothetical chemical compound
1063:Five-membered rings; at least
93:, the majority of drugs, most
76:Heterocyclic organic chemistry
1:
3105:Journal of Chemical Education
2647:
2568:
2489:
1998:4 nitrogen, 4 boron
3084:. Royal Society of Chemistry
3058:. Royal Society of Chemistry
3032:. Royal Society of Chemistry
263:Hantzsch-Widman nomenclature
239:Hantzsch-Widman nomenclature
74:as members of its ring(s).
3230:
2769:1832: Dobereiner produces
2410:
2323:
2094:
1044:
1032:
1004:
976:
948:
907:
29:
2613:
2534:
2455:
2368:
2281:
2202:
2123:
2089:
2086:
2084:
1616:1,2-Dihydro-1,2-azaborine
54:, a heterocyclic compound
3187:13 December 2003 at the
2759:1818: Brugnatelli makes
1717:2 nitrogen, 2
223:tetrasulfur tetranitride
105:-approved drugs contain
2984:10.1351/goldbook.H02737
2904:10.1002/jhet.5570290306
756:("Azolidine" not used)
650:have two sulfur atoms.
3214:Heterocyclic compounds
2858:heterocyclic compounds
2816:) in the genetic code.
2773:(a furan) by treating
2731:, and dibenzoazepine.
1884:Seven-membered rings;
1805:Seven-membered rings;
401:Three-membered rings;
292:Three-membered rings;
261:and do not follow the
211:hexachlorophosphazenes
55:
44:
18:Heterocyclic chemistry
2695:Fused/condensed rings
889:Five-membered rings;
666:Five-membered rings;
554:Four-membered rings;
472:Four-membered rings;
60:heterocyclic compound
50:
42:
3200:(more comprehensive)
3149:on 24 September 2015
2976:Hantzsch–Widman name
2783:1834: Runge obtains
1734:Six-membered rings;
1685:Six-membered rings;
1624:Six-membered rings;
1514:Nitrogen / nitrogen
1494:Six-membered rings;
1200:Six-membered rings;
283:Although subject to
84:organic heterocycles
3117:1986JChEd..63..860C
2995:Smith, Michael B.;
2925:(24): 10257–10274.
1889:
1810:
1739:
1690:
1629:
1499:
1313:(Azinane not used)
1205:
1068:
894:
845:Tetrahydrothiophene
764:("Azole" not used)
671:
559:
477:
406:
297:
1883:
1804:
1800:may be possible.
1733:
1684:
1623:
1546:Sulfur / nitrogen
1529:Oxygen / nitrogen
1493:
1443:-Thiine not used)
1199:
1062:
1006:Nitrogen + sulfur
978:Nitrogen + Oxygen
888:
665:
553:
471:
456:(highly unstable)
436:Nitrogen + oxygen
400:
291:
170:, respectively.
56:
45:
3125:10.1021/ed063p860
3012:978-0-471-72091-1
2931:10.1021/jm501100b
2753:organic chemistry
2737:Phosphaphenalenes
2692:
2691:
2075:
2074:
2009:
2008:
1930:
1929:
1881:
1880:
1765:
1764:
1731:
1730:
1682:
1681:
1621:
1620:
1610:Boron / nitrogen
1491:
1490:
1190:
1189:
1060:
1059:
886:
885:
829:Silacyclopentane
618:
617:
551:
550:
462:
461:
398:
397:
181:are conventional
80:organic chemistry
78:is the branch of
16:(Redirected from
3221:
3159:
3158:
3156:
3154:
3145:. Archived from
3135:
3129:
3128:
3100:
3094:
3093:
3091:
3089:
3078:"Selenopyranium"
3074:
3068:
3067:
3065:
3063:
3048:
3042:
3041:
3039:
3037:
3022:
3016:
3015:
2992:
2986:
2963:
2957:
2956:
2950:
2942:
2914:
2908:
2907:
2887:
2881:
2870:
2861:
2851:
2806:Chargaff's rules
2719:. For azepine,
2688:
2681:
2674:
2667:
2660:
2653:
2609:
2602:
2595:
2588:
2581:
2574:
2530:
2523:
2516:
2509:
2502:
2495:
2451:
2444:
2437:
2430:
2423:
2416:
2364:
2357:
2350:
2343:
2336:
2329:
2277:
2270:
2263:
2256:
2249:
2242:
2198:
2191:
2184:
2177:
2170:
2163:
2082:
2017:
2013:9-membered rings
1939:
1934:8-membered rings
1919:Nitrogen/sulfur
1890:
1811:
1792:7-membered rings
1740:
1691:
1630:
1595:Sulfur / sulfur
1580:Oxygen / oxygen
1563:Oxygen / Sulfur
1500:
1206:
1194:6-membered rings
1069:
950:Oxygen + sulfur
895:
672:
622:5-membered rings
560:
478:
466:4-membered rings
407:
298:
279:3-membered rings
160:dibenzothiophene
21:
3229:
3228:
3224:
3223:
3222:
3220:
3219:
3218:
3204:
3203:
3189:Wayback Machine
3168:
3163:
3162:
3152:
3150:
3137:
3136:
3132:
3102:
3101:
3097:
3087:
3085:
3076:
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3071:
3061:
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3050:
3049:
3045:
3035:
3033:
3024:
3023:
3019:
3013:
2994:
2993:
2989:
2964:
2960:
2943:
2916:
2915:
2911:
2889:
2888:
2884:
2871:
2864:
2854:IUPAC Gold Book
2852:
2848:
2843:
2831:
2823:
2749:
2733:Thienothiophene
2697:
2080:
2015:
2010:
1936:
1931:
1798:homoaromaticity
1794:
1788:
1771:
1766:
1468:Telluropyrylium
1438:
1350:
1321:
1312:
1196:
1191:
1103:
1026:
1014:Isothiazolidine
1012:
998:
984:
970:
958:1,2-Oxathiolane
956:
954:1,3-Oxathiolane
935:
917:
776:Tetrahydrofuran
624:
619:
468:
463:
455:
281:
247:
237:recommends the
232:
228:
220:
216:
208:
204:
195:
193:Inorganic rings
179:tetrahydrofuran
115:
68:cyclic compound
35:
28:
23:
22:
15:
12:
11:
5:
3227:
3225:
3217:
3216:
3206:
3205:
3202:
3201:
3198:Proposition 65
3191:
3179:
3174:
3167:
3166:External links
3164:
3161:
3160:
3130:
3095:
3069:
3043:
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2909:
2898:(3): 639–651.
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1551:Thiomorpholine
1547:
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1526:
1525:
1520:
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1510:
1507:
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1451:
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1444:
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1416:
1411:
1405:
1404:
1401:Selenopyrylium
1398:
1393:
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1382:
1381:
1376:
1371:
1367:
1366:
1360:
1343:
1338:
1334:
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1300:
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1213:
1210:
1197:
1195:
1192:
1188:
1187:
1182:
1180:
1176:
1175:
1174:Thiatetrazole
1172:
1170:
1166:
1165:
1162:
1160:
1156:
1155:
1150:
1148:
1144:
1143:
1138:
1136:
1132:
1131:
1126:
1124:
1120:
1119:
1114:
1112:
1108:
1107:
1098:
1096:
1092:
1091:
1086:
1084:
1080:
1079:
1076:
1073:
1058:
1057:
1052:
1047:
1043:
1042:
1040:
1035:
1031:
1030:
1016:
1007:
1003:
1002:
988:
979:
975:
974:
960:
951:
947:
946:
923:
910:
906:
905:
902:
899:
884:
883:
878:
875:
869:
868:
863:
861:
855:
854:
847:
842:
836:
835:
830:
827:
821:
820:
815:
810:
804:
803:
798:
793:
787:
786:
779:
772:
766:
765:
757:
749:
743:
742:
737:
734:
728:
727:
722:
719:
713:
712:
707:
704:
698:
697:
692:
689:
683:
682:
679:
676:
663:
623:
620:
616:
615:
610:
605:
601:
600:
595:
590:
586:
585:
580:
575:
571:
570:
567:
564:
549:
548:
543:
538:
534:
533:
528:
523:
519:
518:
513:
508:
504:
503:
498:
493:
489:
488:
485:
482:
469:
467:
464:
460:
459:
457:
450:
446:
445:
442:
437:
433:
432:
427:
422:
418:
417:
414:
411:
396:
395:
390:
380:
376:
375:
370:
365:
361:
360:
355:
348:ethylene oxide
341:
337:
336:
331:
326:
322:
321:
318:
313:
309:
308:
305:
302:
289:
280:
277:
276:
275:
268:
265:
255:
246:
245:Notes on lists
243:
230:
226:
218:
214:
206:
202:
194:
191:
144:benzothiophene
114:
113:Classification
111:
109:heterocycles.
64:ring structure
32:Ring structure
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
3226:
3215:
3212:
3211:
3209:
3199:
3195:
3192:
3190:
3186:
3183:
3180:
3178:
3175:
3173:
3170:
3169:
3165:
3148:
3144:
3143:www.ipexl.com
3140:
3134:
3131:
3126:
3122:
3118:
3114:
3110:
3106:
3099:
3096:
3083:
3079:
3073:
3070:
3057:
3053:
3047:
3044:
3031:
3027:
3021:
3018:
3014:
3008:
3004:
3003:
2998:
2991:
2988:
2985:
2981:
2977:
2973:
2972:
2967:
2962:
2959:
2954:
2948:
2940:
2936:
2932:
2928:
2924:
2920:
2913:
2910:
2905:
2901:
2897:
2893:
2886:
2883:
2879:
2878:0-582-27843-0
2875:
2869:
2867:
2863:
2860:
2859:
2855:
2850:
2847:
2840:
2836:
2833:
2832:
2828:
2826:
2820:
2815:
2811:
2807:
2803:
2800:
2796:
2793:
2789:
2786:
2782:
2780:
2779:sulfuric acid
2776:
2772:
2768:
2766:
2762:
2758:
2757:
2756:
2754:
2746:
2744:
2742:
2738:
2734:
2730:
2726:
2722:
2718:
2714:
2710:
2706:
2702:
2694:
2687:
2683:
2680:
2676:
2673:
2669:
2666:
2662:
2659:
2655:
2652:
2648:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2612:
2608:
2604:
2601:
2597:
2594:
2590:
2587:
2583:
2580:
2576:
2573:
2569:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2533:
2529:
2525:
2522:
2518:
2515:
2511:
2508:
2504:
2501:
2497:
2494:
2490:
2486:
2483:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2461:
2458:
2454:
2450:
2446:
2443:
2439:
2436:
2432:
2429:
2425:
2422:
2418:
2415:
2411:
2407:
2406:
2402:
2400:
2399:
2395:
2393:
2392:
2388:
2386:
2383:
2381:
2378:
2376:
2375:
2371:
2367:
2363:
2359:
2356:
2352:
2349:
2345:
2342:
2338:
2335:
2331:
2328:
2324:
2320:
2319:
2315:
2313:
2312:
2308:
2306:
2305:
2301:
2299:
2296:
2294:
2291:
2289:
2288:
2284:
2280:
2276:
2272:
2269:
2265:
2262:
2258:
2255:
2251:
2248:
2244:
2241:
2237:
2236:
2233:
2230:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2208:
2205:
2201:
2197:
2193:
2190:
2186:
2183:
2179:
2176:
2172:
2169:
2165:
2162:
2158:
2157:
2154:
2151:
2149:
2146:
2144:
2141:
2139:
2136:
2134:
2131:
2129:
2126:
2122:
2118:
2115:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2093:
2083:
2077:
2071:
2068:
2066:
2063:
2060:
2059:
2056:
2053:
2051:
2048:
2045:
2044:
2041:
2038:
2036:
2033:
2030:
2029:
2025:
2022:
2019:
2018:
2012:
2005:
2002:
2000:
1997:
1996:
1993:
1990:
1988:
1985:
1982:
1981:
1978:
1975:
1973:
1970:
1967:
1966:
1963:
1960:
1958:
1955:
1952:
1951:
1947:
1944:
1941:
1940:
1933:
1926:
1923:
1921:
1918:
1917:
1914:
1911:
1909:
1906:
1903:
1902:
1898:
1895:
1892:
1891:
1887:
1877:
1874:
1872:
1869:
1866:
1865:
1862:
1859:
1857:
1854:
1851:
1850:
1847:
1844:
1842:
1839:
1836:
1835:
1832:
1829:
1827:
1824:
1823:
1819:
1816:
1813:
1812:
1808:
1801:
1799:
1791:
1789:
1786:
1784:
1780:
1776:
1768:
1761:
1758:
1756:
1753:
1752:
1748:
1745:
1742:
1741:
1737:
1727:
1724:
1722:
1720:
1716:
1715:
1712:
1709:
1707:
1704:
1703:
1699:
1696:
1693:
1692:
1688:
1678:
1676:
1673:
1670:
1669:
1666:
1664:
1661:
1658:
1657:
1654:
1651:
1649:
1646:
1643:
1642:
1638:
1635:
1632:
1631:
1627:
1617:
1614:
1612:
1609:
1608:
1605:
1602:
1600:
1597:
1594:
1593:
1590:
1587:
1585:
1582:
1579:
1578:
1575:
1572:
1570:
1569:
1565:
1562:
1561:
1558:
1555:
1553:
1552:
1548:
1545:
1544:
1541:
1538:
1536:
1535:
1531:
1528:
1527:
1524:
1521:
1519:
1516:
1513:
1512:
1508:
1505:
1502:
1501:
1497:
1487:
1484:
1482:
1479:
1477:
1474:
1473:
1469:
1466:
1464:
1461:
1459:
1456:
1453:
1452:
1448:
1445:
1442:
1437:
1436:
1432:
1430:
1427:
1424:
1423:
1420:
1417:
1415:
1412:
1410:
1407:
1406:
1402:
1399:
1397:
1394:
1392:
1389:
1387:
1384:
1383:
1380:
1377:
1375:
1372:
1369:
1368:
1364:
1361:
1358:
1354:
1349:
1348:
1344:
1342:
1339:
1336:
1335:
1331:
1328:
1325:
1320:
1319:
1315:
1311:
1310:
1306:
1303:
1302:
1299:
1296:
1294:
1291:
1289:
1286:
1285:
1281:
1280:Boratabenzene
1278:
1276:
1273:
1271:
1268:
1266:
1263:
1262:
1259:
1256:
1254:
1252:
1249:
1248:
1245:
1242:
1240:
1237:
1234:
1233:
1230:
1227:
1225:
1222:
1221:
1217:
1214:
1211:
1208:
1207:
1203:
1193:
1186:
1183:
1181:
1178:
1177:
1173:
1171:
1168:
1167:
1164:Oxatetrazole
1163:
1161:
1158:
1157:
1154:
1151:
1149:
1146:
1145:
1142:
1139:
1137:
1134:
1133:
1130:
1127:
1125:
1122:
1121:
1118:
1115:
1113:
1110:
1109:
1106:
1102:
1099:
1097:
1094:
1093:
1090:
1087:
1085:
1082:
1081:
1077:
1074:
1071:
1070:
1066:
1056:
1053:
1051:
1048:
1045:
1041:
1039:
1036:
1033:
1029:
1024:
1020:
1017:
1015:
1011:
1008:
1005:
1001:
996:
992:
989:
987:
986:Isoxazolidine
983:
980:
977:
973:
968:
964:
961:
959:
955:
952:
949:
944:
940:
939:
933:
929:
928:
924:
922:
921:
916:
915:
914:Imidazolidine
911:
908:
903:
900:
897:
896:
892:
882:
879:
876:
874:
871:
870:
867:
864:
862:
860:
857:
856:
853:
852:
848:
846:
843:
841:
838:
837:
834:
831:
828:
826:
823:
822:
819:
816:
814:
811:
809:
806:
805:
802:
799:
797:
794:
792:
789:
788:
785:
784:
780:
778:
777:
773:
771:
768:
767:
763:
762:
758:
755:
754:
750:
748:
745:
744:
741:
738:
735:
733:
730:
729:
726:
723:
720:
718:
715:
714:
711:
708:
705:
703:
700:
699:
696:
693:
690:
688:
685:
684:
680:
677:
674:
673:
669:
662:
660:
656:
651:
649:
645:
641:
637:
633:
629:
621:
614:
611:
609:
606:
603:
602:
599:
596:
594:
591:
588:
587:
584:
581:
579:
576:
573:
572:
568:
565:
562:
561:
557:
547:
544:
542:
539:
536:
535:
532:
529:
527:
524:
521:
520:
517:
514:
512:
509:
506:
505:
502:
499:
497:
494:
491:
490:
486:
483:
480:
479:
475:
465:
458:
454:
451:
448:
447:
443:
441:
438:
435:
434:
431:
428:
426:
423:
420:
419:
415:
412:
409:
408:
404:
394:
391:
388:
384:
381:
378:
377:
374:
371:
369:
366:
363:
362:
359:
356:
353:
349:
345:
342:
339:
338:
335:
332:
330:
327:
324:
323:
319:
317:
314:
311:
310:
306:
303:
300:
299:
295:
288:
286:
278:
273:
269:
266:
264:
260:
256:
253:
249:
248:
244:
242:
240:
236:
224:
212:
200:
192:
190:
188:
184:
180:
176:
171:
169:
165:
161:
157:
153:
149:
145:
141:
137:
136:benzene rings
133:
129:
125:
121:
112:
110:
108:
104:
100:
96:
92:
91:nucleic acids
87:
85:
81:
77:
73:
69:
65:
61:
53:
49:
41:
37:
33:
19:
3151:. Retrieved
3147:the original
3142:
3133:
3108:
3104:
3098:
3086:. Retrieved
3081:
3072:
3060:. Retrieved
3055:
3046:
3034:. Retrieved
3029:
3020:
3001:
2997:March, Jerry
2990:
2969:
2961:
2947:cite journal
2922:
2919:J. Med. Chem
2918:
2912:
2895:
2891:
2885:
2857:
2849:
2824:
2750:
2717:isoquinoline
2698:
2614:9-atom ring
2535:8-atom ring
2456:7-atom ring
2403:
2396:
2389:
2372:
2369:6-atom ring
2316:
2309:
2302:
2285:
2282:5-atom ring
2203:4-atom ring
2124:3-atom ring
2090:Unsaturated
2026:Unsaturated
1948:Unsaturated
1899:Unsaturated
1888:heteroatoms
1885:
1820:Unsaturated
1806:
1795:
1787:
1772:
1749:Unsaturated
1738:heteroatoms
1735:
1700:Unsaturated
1689:heteroatoms
1686:
1639:Unsaturated
1628:heteroatoms
1625:
1566:
1549:
1532:
1509:Unsaturated
1498:heteroatoms
1495:
1463:Telluropyran
1447:Thiopyrylium
1440:
1433:
1352:
1345:
1316:
1307:
1215:Unsaturated
1201:
1078:Unsaturated
1072:Heteroatoms
1067:heteroatoms
1064:
1010:Thiazolidine
936:
925:
920:Pyrazolidine
918:
912:
909:2× nitrogen
898:Heteroatoms
893:heteroatoms
890:
866:Tellurophene
849:
781:
774:
759:
751:
681:Unsaturated
667:
654:
652:
640:isothiazoles
627:
625:
574:2× Nitrogen
569:Unsaturated
563:Heteroatoms
558:heteroatoms
555:
487:Unsaturated
473:
421:2× Nitrogen
416:Unsaturated
410:Heteroatoms
405:heteroatoms
402:
307:Unsaturated
293:
282:
221:rings), and
196:
172:
168:dibenzofuran
116:
88:
83:
75:
63:
59:
57:
36:
3153:8 September
3111:(10): 860.
2835:Spiroketals
2814:pyrimidines
2721:benzazepine
2701:carbocyclic
2287:Pyrrolidine
2020:Heteroatom
1942:Heteroatom
1893:Heteroatom
1814:Heteroatom
1809:heteroatom
1743:Heteroatom
1726:Carborazine
1694:Heteroatom
1633:Heteroatom
1503:Heteroatom
1396:Selenopyran
1379:Phosphinine
1374:Phosphinane
1370:Phosphorus
1209:Heteroatom
1204:heteroatom
1117:Thiadiazole
1028:Isothiazole
982:Oxazolidine
972:Isoxathiole
967:Oxathioline
932:Imidazoline
877:Stannolane
818:Selenophene
796:Phospholane
753:Pyrrolidine
675:Heteroatom
670:heteroatom
659:dithiazoles
648:Dithiolanes
578:Diazetidine
526:Phosphetane
522:Phosphorus
481:Heteroatom
476:heteroatom
440:Oxaziridine
425:Diaziridine
387:episulfides
373:Phosphirene
368:Phosphirane
364:Phosphorus
301:Heteroatom
296:heteroatom
285:ring strain
3082:ChemSpider
3056:ChemSpider
3030:chemspider
3026:"Stibinin"
2841:References
2792:indigo dye
2374:Piperidine
2095:Heteroatom
2023:Saturated
2004:Borazocine
1945:Saturated
1925:Thiazepine
1896:Saturated
1817:Saturated
1746:Saturated
1697:Saturated
1648:Triazinane
1636:Saturated
1534:Morpholine
1506:Saturated
1481:Stanninane
1454:Tellurium
1359:not used)
1330:Pyridinium
1326:not used)
1309:Piperidine
1212:Saturated
1179:N N N N N
1169:N N N N S
1159:N N N N O
1141:Dithiazole
1105:Oxadiazole
1075:Saturated
1050:Dithiolane
1046:2× sulfur
1034:2× oxygen
1023:Thiazoline
943:Pyrazoline
901:Saturated
813:Selenolane
791:Phosphorus
721:Bismolane
691:Stibolane
678:Saturated
642:contain a
608:Dithietane
604:2× Sulfur
589:2× Oxygen
566:Saturated
484:Saturated
449:2× Oxygen
444:Oxazirine
413:Saturated
304:Saturated
175:piperidine
152:benzofuran
2765:uric acid
2741:phenalene
2725:carbazole
2713:quinoline
2709:isoindole
2405:Thiopyran
2318:Thiophene
2207:Azetidine
2128:Aziridine
2087:Saturated
2031:Nitrogen
1953:Nitrogen
1913:Diazepine
1908:Diazepane
1904:Nitrogen
1837:Nitrogen
1760:Pentazine
1754:Nitrogen
1711:Tetrazine
1705:Nitrogen
1675:Trithiane
1644:Nitrogen
1568:Oxathiane
1518:Diazinane
1458:Tellurane
1435:Thiopyran
1304:Nitrogen
1293:Germinane
1288:Germanium
1223:Antimony
1185:Pentazole
1153:Tetrazole
1129:Dioxazole
1089:Triazoles
1038:Dioxolane
1000:Isoxazole
995:Oxazoline
963:Oxathiole
927:Imidazole
859:Tellurium
851:Thiophene
801:Phosphole
736:Borolane
706:Arsolane
636:Thiazoles
593:Dioxetane
531:Phosphete
496:Azetidine
492:Nitrogen
453:Dioxirane
430:Diazirine
329:Aziridine
325:Nitrogen
320:Borirene
164:carbazole
140:quinoline
124:thiophene
99:cellulose
3208:Category
3185:Archived
3052:"Bismin"
2999:(2007),
2939:25255204
2829:See also
2771:furfural
2729:acridine
2643:Thionine
2628:Thionane
2564:Thiocine
2549:Thiocane
2485:Thiepine
2470:Thiepane
2391:Pyridine
2298:Thiolane
2217:Thietane
2153:Thiirene
2138:Thiirane
2113:Nitrogen
2099:Nitrogen
2070:Thionine
2065:Thionane
1992:Thiocine
1987:Thiocane
1876:Thiepine
1871:Thiepane
1783:Borazine
1779:hexazine
1663:Trioxane
1653:Triazine
1599:Dithiane
1574:Oxathiin
1557:Thiazine
1486:Stannine
1414:Silinane
1391:Selenane
1386:Selenium
1363:Pyrylium
1318:Pyridine
1275:Borinine
1270:Borinane
1244:Arsinine
1239:Arsinane
1235:Arsenic
1229:Stibinin
1147:N N N N
1055:Dithiole
1019:Thiazole
938:Pyrazole
881:Stannole
808:Selenium
747:Nitrogen
687:Antimony
613:Dithiete
541:Thietane
393:Thiirene
383:Thiirane
352:epoxides
316:Borirane
199:borazine
156:acridine
120:pyridine
107:nitrogen
72:elements
52:Pyridine
3113:Bibcode
3088:11 June
3062:11 June
3036:11 June
2810:purines
2785:pyrrole
2761:alloxan
2638:Oxonine
2633:Azonine
2623:Oxonane
2618:Azonane
2559:Oxocine
2554:Azocine
2544:Oxocane
2539:Azocane
2480:Oxepine
2475:Azepine
2465:Oxepane
2460:Azepane
2304:Pyrrole
2293:Oxolane
2212:Oxetane
2148:Oxirene
2143:Azirine
2133:Oxirane
2119:Sulfur
2061:Sulfur
2055:Oxonine
2050:Oxonane
2046:Oxygen
2040:Azonine
2035:Azonane
1983:Sulfur
1977:Oxocine
1972:Oxocane
1968:Oxygen
1962:Azocine
1957:Azocane
1867:Sulfur
1861:Oxepine
1856:Oxepane
1852:Oxygen
1846:Azepine
1841:Azepane
1831:Borepin
1671:Sulfur
1659:Oxygen
1604:Dithiin
1589:Dioxine
1584:Dioxane
1540:Oxazine
1523:Diazine
1470:cation
1449:cation
1425:Sulfur
1409:Silicon
1403:cation
1365:cation
1337:Oxygen
1332:cation
1298:Germine
1251:Bismuth
1101:Furazan
991:Oxazole
825:Silicon
761:Pyrrole
725:Bismole
717:Bismuth
702:Arsenic
695:Stibole
598:Dioxete
583:Diazete
537:Sulfur
511:Oxetane
507:Oxygen
379:Sulfur
358:Oxirene
344:Oxirane
340:Oxygen
334:Azirine
272:isomers
209:ring),
128:pyrrole
95:biomass
3009:
2937:
2876:
2804:1951:
2799:Treibs
2797:1936:
2775:starch
2705:indole
2385:Thiane
2232:Thiete
2116:Oxygen
2109:Sulfur
2104:Oxygen
1825:Boron
1429:Thiane
1419:Siline
1282:anion
1258:Bismin
1135:N S S
1123:N O O
1111:N N S
1095:N N O
1083:N N N
840:Sulfur
833:Silole
770:Oxygen
740:Borole
710:Arsole
644:sulfur
632:azoles
546:Thiete
312:Boron
254:atoms.
252:carbon
187:ethers
183:amines
166:, and
150:, and
148:indole
130:, and
2966:IUPAC
2777:with
2763:from
2398:Pyran
2380:Oxane
2311:Furan
2227:Oxete
2222:Azete
1719:boron
1626:three
1357:Oxine
1347:Pyran
1341:Oxane
1324:Azine
1265:Boron
1218:Ions
1065:three
783:Furan
732:Boron
655:three
516:Oxete
501:Azete
259:IUPAC
235:IUPAC
132:furan
66:is a
3155:2010
3090:2018
3064:2018
3038:2018
3007:ISBN
2953:link
2935:PMID
2874:ISBN
2821:Uses
2812:and
1773:The
1736:five
1687:four
638:and
185:and
177:and
3121:doi
2980:doi
2978:".
2927:doi
2900:doi
2715:or
2707:or
1886:two
1807:one
1781:.
1496:two
1476:Tin
1202:one
891:two
873:Tin
668:one
634:.
628:two
556:two
474:one
403:two
294:one
103:FDA
62:or
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3196:,
3141:.
3119:.
3109:63
3107:.
3080:.
3054:.
3028:.
2968:,
2949:}}
2945:{{
2933:.
2923:57
2921:.
2896:29
2894:.
2865:^
2743:.
2727:,
1439:(2
1351:(2
945:)
389:)
354:)
350:,
213:(P
201:(B
162:,
158:,
146:,
142:,
126:,
122:,
86:.
58:A
3157:.
3127:.
3123::
3115::
3092:.
3066:.
3040:.
2982::
2955:)
2941:.
2929::
2906:.
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1441:H
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1353:H
1322:(
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1021:(
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993:(
969:)
965:(
941:(
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930:(
385:(
346:(
274:.
231:4
229:N
227:4
225:S
219:3
217:N
215:3
207:3
205:N
203:3
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