2316:
2410:
2323:
2229:
2503:
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29:
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2250:
2157:
2403:
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2150:
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2496:
2510:
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2424:
2417:
2337:
2185:
2164:
2257:
2596:
2517:
2589:
2264:
2675:
2654:
2178:
2171:
2668:
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2647:
2640:
2575:
2561:
2582:
2568:
2243:
2489:
2344:
37:
2236:
106:
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
2906:
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".
143:, 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
162:
Heterocyclic organic compounds can be usefully classified based on their electronic structure. The saturated organic heterocycles behave like the acyclic derivatives. Thus,
3173:
1785:
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,
2692:
or heterocyclic, have a variety of common and systematic names. For example, with the benzo-fused unsaturated nitrogen heterocycles, pyrrole provides
2954:
1002:
223:
2941:
222:. In comparison with organic heterocycles, which have numerous commercial applications, inorganic ring systems are mainly of theoretical interest.
1451:
628:
1384:
960:
955:
636:
566:
1469:
801:
3127:
1896:
1281:
1117:
951:
519:
2616:
2552:
2537:
2053:
1980:
1975:
1562:
1402:
1379:
1258:
1227:
3066:
2611:
2606:
2547:
2532:
2038:
2023:
1965:
1960:
586:
571:
3040:
178:, with modified steric profiles. Therefore, the study of organic heterocyclic chemistry focuses on organic unsaturated rings.
2999:
90:
and related materials), and many natural and synthetic dyes. More than half of known compounds are heterocycles. 59% of US
2814:
Heterocyclic compounds are pervasive in many areas of life sciences and technology. Many drugs are heterocyclic compounds.
3170:
2315:
2866:
3202:
20:
1763:
3182:
2712:
is the preferred name. Likewise, the compounds with two benzene rings fused to the central heterocycle are
251:
227:
3165:
2989:
2409:
2228:
1604:
2322:
2861:
Thomas L. Gilchrist "Heterocyclic
Chemistry" 3rd ed. Addison Wesley: Essex, England, 1997. 414 pp.
2502:
2329:
211:
2790:
isolates chlorophyll derivatives from crude oil, explaining the biological origin of petroleum.
2631:
2437:
2058:
3135:
2156:
2935:
2249:
199:
2402:
127:. For example, the fused benzene derivatives of pyridine, thiophene, pyrrole, and furan are
3101:
3014:
2740:
The history of heterocyclic chemistry began in the 1800s, in step with the development of
2350:
2149:
8:
3092:
Campaigne, E. (1986). "Adrien Albert and the rationalization of heterocyclic chemistry".
2794:
2595:
2516:
1312:
833:
3105:
2688:
Heterocyclic rings systems that are formally derived by fusion with other rings, either
2674:
2653:
2588:
2574:
2495:
2423:
2242:
2184:
2163:
2667:
2660:
2646:
2639:
2581:
2567:
2560:
2509:
2481:
2336:
2263:
2728:
are a tricyclic phosphorus-containing heterocyclic system derived from the carbocycle
2488:
2430:
2416:
2235:
2177:
2170:
2995:
2923:
2862:
2741:
2256:
68:
2964:
1774:
is a six-membered ring with three nitrogen heteroatoms and three boron heteroatoms.
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2915:
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2787:
2725:
2343:
148:
60:
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1456:
946:
942:
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256:
Some of the names refer to classes of compounds rather than individual compounds.
167:
56:
3186:
1539:
1389:
336:
132:
2905:
3196:
2963:, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "
2767:
1268:
974:
902:
79:
2972:
2892:
619:
heteroatoms, at least one of which is nitrogen, are collectively called the
2927:
2705:
1435:
998:
908:
854:
156:
124:
2985:
2823:
2709:
2275:
1714:
1367:
1362:
1105:
1016:
970:
920:
806:
784:
741:
514:
428:
413:
361:
356:
273:
2845:
2783:, allowing synthetic chemistry to displace a large agricultural industry
123:. Another large class of organic heterocycles refers to those fused to
28:
2879:
Rees, Charles W. (1992). "Polysulfur-Nitrogen
Heterocyclic Chemistry".
2802:
2780:
2689:
2362:
1992:
1913:
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1318:
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1129:
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163:
140:
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2729:
2713:
2701:
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1663:
1556:
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624:
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317:
152:
128:
112:
87:
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2473:
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187:
144:
108:
95:
40:
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2453:
2448:
2292:
2281:
2200:
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2043:
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1950:
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1844:
1834:
1829:
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813:
749:
713:
705:
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499:
346:
340:
332:
322:
260:
116:
83:
2991:
Advanced
Organic Chemistry: Reactions, Mechanisms, and Structure
2797:
are described, highlighting the role of heterocyclic compounds (
3171:
List of known and probable carcinogens, American Cancer
Society
2798:
2763:
2693:
2373:
2220:
2097:
2092:
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1407:
1246:
828:
821:
758:
728:
698:
632:
620:
534:
240:
175:
171:
136:
16:
Molecule with one or more rings composed of different elements
2983:
2386:
2368:
2299:
2215:
2210:
1707:
1345:
1335:
1329:
1253:
771:
720:
646:
or more heteroatoms also exists. One example is the class of
504:
489:
247:
120:
71:
dealing with the synthesis, properties, and applications of
36:
1757:
1464:
861:
91:
650:, which contain two sulfur atoms and one nitrogen atom.
276:, 3-membered heterocyclic rings are well characterized.
3128:"IPEXL.com Multilingual Patent Search, Patent Ranking"
2700:
depending on the orientation. The pyridine analog is
2066:
78:
Examples of heterocyclic compounds include all of the
32:
Structures and names of common heterocyclic compounds
3183:
List of known carcinogens by the State of
California
2735:
186:Some heterocycles contain no carbon. Examples are
3194:
642:A large group of 5-membered ring compounds with
239:"Heteroatoms" are atoms in the ring other than
2994:(6th ed.), New York: Wiley-Interscience,
2940:: CS1 maint: multiple names: authors list (
2857:
2855:
3166:Heterocyclic amines in cooked meat, US CDC
2776:("fiery oil") by dry distillation of bones
3091:
615:The 5-membered ring compounds containing
59:that has atoms of at least two different
2852:
2683:
893:Unsaturated (and partially unsaturated)
35:
27:
19:For other uses of "ring structure", see
2724:are the fusion of two thiophene rings.
1766:with six nitrogen heteroatoms would be
1758:Six-membered rings with six heteroatoms
3195:
3059:
3033:
3007:
2878:
3161:Hantzsch-Widman nomenclature, IUPAC
2872:
2067:Images of rings with one heteroatom
2001:
1922:
1780:
1182:
610:
454:
267:
230:for naming heterocyclic compounds.
13:
2960:Compendium of Chemical Terminology
635:and a nitrogen atom in the ring.
181:
14:
3214:
3154:
2881:Journal of Heterocyclic Chemistry
2744:. Some noteworthy developments:
2736:History of heterocyclic chemistry
246:Names in italics are retained by
233:
101:
2673:
2666:
2659:
2652:
2645:
2638:
2594:
2587:
2580:
2573:
2566:
2559:
2515:
2508:
2501:
2494:
2487:
2480:
2436:
2429:
2422:
2415:
2408:
2401:
2349:
2342:
2335:
2328:
2321:
2314:
2262:
2255:
2248:
2241:
2234:
2227:
2183:
2176:
2169:
2162:
2155:
2148:
259:Also no attempt is made to list
3120:
3085:
2977:
2948:
2899:
2836:
2779:1906: Friedlander synthesizes
1764:hypothetical chemical compound
1052:Five-membered rings; at least
82:, the majority of drugs, most
65:Heterocyclic organic chemistry
1:
3094:Journal of Chemical Education
2829:
2636:
2557:
2478:
1987:4 nitrogen, 4 boron
3073:. Royal Society of Chemistry
3047:. Royal Society of Chemistry
3021:. Royal Society of Chemistry
252:Hantzsch-Widman nomenclature
228:Hantzsch-Widman nomenclature
7:
2817:
63:as members of its ring(s).
10:
3219:
2758:1832: Dobereiner produces
2399:
2312:
2083:
1033:
1021:
993:
965:
937:
896:
18:
2602:
2523:
2444:
2357:
2270:
2191:
2112:
2078:
2075:
2073:
1605:1,2-Dihydro-1,2-azaborine
43:, a heterocyclic compound
3176:13 December 2003 at the
2748:1818: Brugnatelli makes
1706:2 nitrogen, 2
212:tetrasulfur tetranitride
94:-approved drugs contain
2973:10.1351/goldbook.H02737
2893:10.1002/jhet.5570290306
2809:
745:("Azolidine" not used)
639:have two sulfur atoms.
3203:Heterocyclic compounds
2847:heterocyclic compounds
2805:) in the genetic code.
2762:(a furan) by treating
2720:, and dibenzoazepine.
1873:Seven-membered rings;
1794:Seven-membered rings;
390:Three-membered rings;
281:Three-membered rings;
250:and do not follow the
200:hexachlorophosphazenes
44:
33:
2684:Fused/condensed rings
878:Five-membered rings;
655:Five-membered rings;
543:Four-membered rings;
461:Four-membered rings;
49:heterocyclic compound
39:
31:
3189:(more comprehensive)
3138:on 24 September 2015
2965:Hantzsch–Widman name
2772:1834: Runge obtains
1723:Six-membered rings;
1674:Six-membered rings;
1613:Six-membered rings;
1503:Nitrogen / nitrogen
1483:Six-membered rings;
1189:Six-membered rings;
272:Although subject to
73:organic heterocycles
3106:1986JChEd..63..860C
2984:Smith, Michael B.;
2914:(24): 10257–10274.
1878:
1799:
1728:
1679:
1618:
1488:
1302:(Azinane not used)
1194:
1057:
883:
834:Tetrahydrothiophene
753:("Azole" not used)
660:
548:
466:
395:
286:
1872:
1793:
1789:may be possible.
1722:
1673:
1612:
1535:Sulfur / nitrogen
1518:Oxygen / nitrogen
1482:
1432:-Thiine not used)
1188:
1051:
995:Nitrogen + sulfur
967:Nitrogen + Oxygen
877:
654:
542:
460:
445:(highly unstable)
425:Nitrogen + oxygen
389:
280:
159:, respectively.
45:
34:
3114:10.1021/ed063p860
3001:978-0-471-72091-1
2920:10.1021/jm501100b
2742:organic chemistry
2726:Phosphaphenalenes
2681:
2680:
2064:
2063:
1998:
1997:
1919:
1918:
1870:
1869:
1754:
1753:
1720:
1719:
1671:
1670:
1610:
1609:
1599:Boron / nitrogen
1480:
1479:
1179:
1178:
1049:
1048:
875:
874:
818:Silacyclopentane
607:
606:
540:
539:
451:
450:
387:
386:
170:are conventional
69:organic chemistry
67:is the branch of
3210:
3148:
3147:
3145:
3143:
3134:. Archived from
3124:
3118:
3117:
3089:
3083:
3082:
3080:
3078:
3067:"Selenopyranium"
3063:
3057:
3056:
3054:
3052:
3037:
3031:
3030:
3028:
3026:
3011:
3005:
3004:
2981:
2975:
2952:
2946:
2945:
2939:
2931:
2903:
2897:
2896:
2876:
2870:
2859:
2850:
2840:
2795:Chargaff's rules
2708:. For azepine,
2677:
2670:
2663:
2656:
2649:
2642:
2598:
2591:
2584:
2577:
2570:
2563:
2519:
2512:
2505:
2498:
2491:
2484:
2440:
2433:
2426:
2419:
2412:
2405:
2353:
2346:
2339:
2332:
2325:
2318:
2266:
2259:
2252:
2245:
2238:
2231:
2187:
2180:
2173:
2166:
2159:
2152:
2071:
2070:
2006:
2005:
2002:9-membered rings
1928:
1927:
1923:8-membered rings
1908:Nitrogen/sulfur
1879:
1871:
1800:
1792:
1781:7-membered rings
1729:
1721:
1680:
1672:
1619:
1611:
1584:Sulfur / sulfur
1569:Oxygen / oxygen
1552:Oxygen / Sulfur
1489:
1481:
1195:
1187:
1183:6-membered rings
1058:
1050:
939:Oxygen + sulfur
884:
876:
661:
653:
611:5-membered rings
549:
541:
467:
459:
455:4-membered rings
396:
388:
287:
279:
268:3-membered rings
149:dibenzothiophene
3218:
3217:
3213:
3212:
3211:
3209:
3208:
3207:
3193:
3192:
3178:Wayback Machine
3157:
3152:
3151:
3141:
3139:
3126:
3125:
3121:
3090:
3086:
3076:
3074:
3065:
3064:
3060:
3050:
3048:
3039:
3038:
3034:
3024:
3022:
3013:
3012:
3008:
3002:
2982:
2978:
2953:
2949:
2933:
2932:
2904:
2900:
2877:
2873:
2860:
2853:
2843:IUPAC Gold Book
2841:
2837:
2832:
2820:
2812:
2738:
2722:Thienothiophene
2686:
2069:
2004:
1999:
1925:
1920:
1787:homoaromaticity
1783:
1777:
1760:
1755:
1457:Telluropyrylium
1427:
1339:
1310:
1301:
1185:
1180:
1092:
1015:
1003:Isothiazolidine
1001:
987:
973:
959:
947:1,2-Oxathiolane
945:
943:1,3-Oxathiolane
924:
906:
765:Tetrahydrofuran
613:
608:
457:
452:
444:
270:
236:
226:recommends the
221:
217:
209:
205:
197:
193:
184:
182:Inorganic rings
168:tetrahydrofuran
104:
57:cyclic compound
24:
17:
12:
11:
5:
3216:
3206:
3205:
3191:
3190:
3187:Proposition 65
3180:
3168:
3163:
3156:
3155:External links
3153:
3150:
3149:
3119:
3084:
3058:
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2898:
2887:(3): 639–651.
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1540:Thiomorpholine
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1433:
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1394:
1393:
1390:Selenopyrylium
1387:
1382:
1377:
1371:
1370:
1365:
1360:
1356:
1355:
1349:
1332:
1327:
1323:
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1171:
1169:
1165:
1164:
1163:Thiatetrazole
1161:
1159:
1155:
1154:
1151:
1149:
1145:
1144:
1139:
1137:
1133:
1132:
1127:
1125:
1121:
1120:
1115:
1113:
1109:
1108:
1103:
1101:
1097:
1096:
1087:
1085:
1081:
1080:
1075:
1073:
1069:
1068:
1065:
1062:
1047:
1046:
1041:
1036:
1032:
1031:
1029:
1024:
1020:
1019:
1005:
996:
992:
991:
977:
968:
964:
963:
949:
940:
936:
935:
912:
899:
895:
894:
891:
888:
873:
872:
867:
864:
858:
857:
852:
850:
844:
843:
836:
831:
825:
824:
819:
816:
810:
809:
804:
799:
793:
792:
787:
782:
776:
775:
768:
761:
755:
754:
746:
738:
732:
731:
726:
723:
717:
716:
711:
708:
702:
701:
696:
693:
687:
686:
681:
678:
672:
671:
668:
665:
652:
612:
609:
605:
604:
599:
594:
590:
589:
584:
579:
575:
574:
569:
564:
560:
559:
556:
553:
538:
537:
532:
527:
523:
522:
517:
512:
508:
507:
502:
497:
493:
492:
487:
482:
478:
477:
474:
471:
458:
456:
453:
449:
448:
446:
439:
435:
434:
431:
426:
422:
421:
416:
411:
407:
406:
403:
400:
385:
384:
379:
369:
365:
364:
359:
354:
350:
349:
344:
337:ethylene oxide
330:
326:
325:
320:
315:
311:
310:
307:
302:
298:
297:
294:
291:
278:
269:
266:
265:
264:
257:
254:
244:
235:
234:Notes on lists
232:
219:
215:
207:
203:
195:
191:
183:
180:
133:benzothiophene
103:
102:Classification
100:
98:heterocycles.
53:ring structure
21:Ring structure
15:
9:
6:
4:
3:
2:
3215:
3204:
3201:
3200:
3198:
3188:
3184:
3181:
3179:
3175:
3172:
3169:
3167:
3164:
3162:
3159:
3158:
3137:
3133:
3132:www.ipexl.com
3129:
3123:
3115:
3111:
3107:
3103:
3099:
3095:
3088:
3072:
3068:
3062:
3046:
3042:
3036:
3020:
3016:
3010:
3003:
2997:
2993:
2992:
2987:
2980:
2974:
2970:
2966:
2962:
2961:
2956:
2951:
2943:
2937:
2929:
2925:
2921:
2917:
2913:
2909:
2902:
2894:
2890:
2886:
2882:
2875:
2868:
2867:0-582-27843-0
2864:
2858:
2856:
2849:
2848:
2844:
2839:
2835:
2825:
2822:
2821:
2815:
2804:
2800:
2796:
2792:
2789:
2785:
2782:
2778:
2775:
2771:
2769:
2768:sulfuric acid
2765:
2761:
2757:
2755:
2751:
2747:
2746:
2745:
2743:
2733:
2731:
2727:
2723:
2719:
2715:
2711:
2707:
2703:
2699:
2695:
2691:
2676:
2672:
2669:
2665:
2662:
2658:
2655:
2651:
2648:
2644:
2641:
2637:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2601:
2597:
2593:
2590:
2586:
2583:
2579:
2576:
2572:
2569:
2565:
2562:
2558:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2522:
2518:
2514:
2511:
2507:
2504:
2500:
2497:
2493:
2490:
2486:
2483:
2479:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2452:
2450:
2447:
2443:
2439:
2435:
2432:
2428:
2425:
2421:
2418:
2414:
2411:
2407:
2404:
2400:
2396:
2395:
2391:
2389:
2388:
2384:
2382:
2381:
2377:
2375:
2372:
2370:
2367:
2365:
2364:
2360:
2356:
2352:
2348:
2345:
2341:
2338:
2334:
2331:
2327:
2324:
2320:
2317:
2313:
2309:
2308:
2304:
2302:
2301:
2297:
2295:
2294:
2290:
2288:
2285:
2283:
2280:
2278:
2277:
2273:
2269:
2265:
2261:
2258:
2254:
2251:
2247:
2244:
2240:
2237:
2233:
2230:
2226:
2225:
2222:
2219:
2217:
2214:
2212:
2209:
2207:
2204:
2202:
2199:
2197:
2194:
2190:
2186:
2182:
2179:
2175:
2172:
2168:
2165:
2161:
2158:
2154:
2151:
2147:
2146:
2143:
2140:
2138:
2135:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2111:
2107:
2104:
2101:
2099:
2096:
2094:
2091:
2089:
2086:
2082:
2072:
2060:
2057:
2055:
2052:
2049:
2048:
2045:
2042:
2040:
2037:
2034:
2033:
2030:
2027:
2025:
2022:
2019:
2018:
2014:
2011:
2008:
2007:
1994:
1991:
1989:
1986:
1985:
1982:
1979:
1977:
1974:
1971:
1970:
1967:
1964:
1962:
1959:
1956:
1955:
1952:
1949:
1947:
1944:
1941:
1940:
1936:
1933:
1930:
1929:
1915:
1912:
1910:
1907:
1906:
1903:
1900:
1898:
1895:
1892:
1891:
1887:
1884:
1881:
1880:
1876:
1866:
1863:
1861:
1858:
1855:
1854:
1851:
1848:
1846:
1843:
1840:
1839:
1836:
1833:
1831:
1828:
1825:
1824:
1821:
1818:
1816:
1813:
1812:
1808:
1805:
1802:
1801:
1797:
1790:
1788:
1778:
1775:
1773:
1769:
1765:
1750:
1747:
1745:
1742:
1741:
1737:
1734:
1731:
1730:
1726:
1716:
1713:
1711:
1709:
1705:
1704:
1701:
1698:
1696:
1693:
1692:
1688:
1685:
1682:
1681:
1677:
1667:
1665:
1662:
1659:
1658:
1655:
1653:
1650:
1647:
1646:
1643:
1640:
1638:
1635:
1632:
1631:
1627:
1624:
1621:
1620:
1616:
1606:
1603:
1601:
1598:
1597:
1594:
1591:
1589:
1586:
1583:
1582:
1579:
1576:
1574:
1571:
1568:
1567:
1564:
1561:
1559:
1558:
1554:
1551:
1550:
1547:
1544:
1542:
1541:
1537:
1534:
1533:
1530:
1527:
1525:
1524:
1520:
1517:
1516:
1513:
1510:
1508:
1505:
1502:
1501:
1497:
1494:
1491:
1490:
1486:
1476:
1473:
1471:
1468:
1466:
1463:
1462:
1458:
1455:
1453:
1450:
1448:
1445:
1442:
1441:
1437:
1434:
1431:
1426:
1425:
1421:
1419:
1416:
1413:
1412:
1409:
1406:
1404:
1401:
1399:
1396:
1395:
1391:
1388:
1386:
1383:
1381:
1378:
1376:
1373:
1372:
1369:
1366:
1364:
1361:
1358:
1357:
1353:
1350:
1347:
1343:
1338:
1337:
1333:
1331:
1328:
1325:
1324:
1320:
1317:
1314:
1309:
1308:
1304:
1300:
1299:
1295:
1292:
1291:
1288:
1285:
1283:
1280:
1278:
1275:
1274:
1270:
1269:Boratabenzene
1267:
1265:
1262:
1260:
1257:
1255:
1252:
1251:
1248:
1245:
1243:
1241:
1238:
1237:
1234:
1231:
1229:
1226:
1223:
1222:
1219:
1216:
1214:
1211:
1210:
1206:
1203:
1200:
1197:
1196:
1192:
1175:
1172:
1170:
1167:
1166:
1162:
1160:
1157:
1156:
1153:Oxatetrazole
1152:
1150:
1147:
1146:
1143:
1140:
1138:
1135:
1134:
1131:
1128:
1126:
1123:
1122:
1119:
1116:
1114:
1111:
1110:
1107:
1104:
1102:
1099:
1098:
1095:
1091:
1088:
1086:
1083:
1082:
1079:
1076:
1074:
1071:
1070:
1066:
1063:
1060:
1059:
1055:
1045:
1042:
1040:
1037:
1034:
1030:
1028:
1025:
1022:
1018:
1013:
1009:
1006:
1004:
1000:
997:
994:
990:
985:
981:
978:
976:
975:Isoxazolidine
972:
969:
966:
962:
957:
953:
950:
948:
944:
941:
938:
933:
929:
928:
922:
918:
917:
913:
911:
910:
905:
904:
903:Imidazolidine
900:
897:
892:
889:
886:
885:
881:
871:
868:
865:
863:
860:
859:
856:
853:
851:
849:
846:
845:
842:
841:
837:
835:
832:
830:
827:
826:
823:
820:
817:
815:
812:
811:
808:
805:
803:
800:
798:
795:
794:
791:
788:
786:
783:
781:
778:
777:
774:
773:
769:
767:
766:
762:
760:
757:
756:
752:
751:
747:
744:
743:
739:
737:
734:
733:
730:
727:
724:
722:
719:
718:
715:
712:
709:
707:
704:
703:
700:
697:
694:
692:
689:
688:
685:
682:
679:
677:
674:
673:
669:
666:
663:
662:
658:
651:
649:
645:
640:
638:
634:
630:
626:
622:
618:
603:
600:
598:
595:
592:
591:
588:
585:
583:
580:
577:
576:
573:
570:
568:
565:
562:
561:
557:
554:
551:
550:
546:
536:
533:
531:
528:
525:
524:
521:
518:
516:
513:
510:
509:
506:
503:
501:
498:
495:
494:
491:
488:
486:
483:
480:
479:
475:
472:
469:
468:
464:
447:
443:
440:
437:
436:
432:
430:
427:
424:
423:
420:
417:
415:
412:
409:
408:
404:
401:
398:
397:
393:
383:
380:
377:
373:
370:
367:
366:
363:
360:
358:
355:
352:
351:
348:
345:
342:
338:
334:
331:
328:
327:
324:
321:
319:
316:
313:
312:
308:
306:
303:
300:
299:
295:
292:
289:
288:
284:
277:
275:
262:
258:
255:
253:
249:
245:
242:
238:
237:
231:
229:
225:
213:
201:
189:
179:
177:
173:
169:
165:
160:
158:
154:
150:
146:
142:
138:
134:
130:
126:
125:benzene rings
122:
118:
114:
110:
99:
97:
93:
89:
85:
81:
80:nucleic acids
76:
74:
70:
66:
62:
58:
54:
50:
42:
38:
30:
26:
22:
3140:. Retrieved
3136:the original
3131:
3122:
3097:
3093:
3087:
3075:. Retrieved
3070:
3061:
3049:. Retrieved
3044:
3035:
3023:. Retrieved
3018:
3009:
2990:
2986:March, Jerry
2979:
2958:
2950:
2936:cite journal
2911:
2908:J. Med. Chem
2907:
2901:
2884:
2880:
2874:
2846:
2838:
2813:
2739:
2706:isoquinoline
2687:
2603:9-atom ring
2524:8-atom ring
2445:7-atom ring
2392:
2385:
2378:
2361:
2358:6-atom ring
2305:
2298:
2291:
2274:
2271:5-atom ring
2192:4-atom ring
2113:3-atom ring
2079:Unsaturated
2015:Unsaturated
1937:Unsaturated
1888:Unsaturated
1877:heteroatoms
1874:
1809:Unsaturated
1795:
1784:
1776:
1761:
1738:Unsaturated
1727:heteroatoms
1724:
1689:Unsaturated
1678:heteroatoms
1675:
1628:Unsaturated
1617:heteroatoms
1614:
1555:
1538:
1521:
1498:Unsaturated
1487:heteroatoms
1484:
1452:Telluropyran
1436:Thiopyrylium
1429:
1422:
1341:
1334:
1305:
1296:
1204:Unsaturated
1190:
1067:Unsaturated
1061:Heteroatoms
1056:heteroatoms
1053:
999:Thiazolidine
925:
914:
909:Pyrazolidine
907:
901:
898:2× nitrogen
887:Heteroatoms
882:heteroatoms
879:
855:Tellurophene
838:
770:
763:
748:
740:
670:Unsaturated
656:
643:
641:
629:isothiazoles
616:
614:
563:2× Nitrogen
558:Unsaturated
552:Heteroatoms
547:heteroatoms
544:
476:Unsaturated
462:
410:2× Nitrogen
405:Unsaturated
399:Heteroatoms
394:heteroatoms
391:
296:Unsaturated
282:
271:
210:rings), and
185:
161:
157:dibenzofuran
105:
77:
72:
64:
52:
48:
46:
25:
3142:8 September
3100:(10): 860.
2824:Spiroketals
2803:pyrimidines
2710:benzazepine
2690:carbocyclic
2276:Pyrrolidine
2009:Heteroatom
1931:Heteroatom
1882:Heteroatom
1803:Heteroatom
1798:heteroatom
1732:Heteroatom
1715:Carborazine
1683:Heteroatom
1622:Heteroatom
1492:Heteroatom
1385:Selenopyran
1368:Phosphinine
1363:Phosphinane
1359:Phosphorus
1198:Heteroatom
1193:heteroatom
1106:Thiadiazole
1017:Isothiazole
971:Oxazolidine
961:Isoxathiole
956:Oxathioline
921:Imidazoline
866:Stannolane
807:Selenophene
785:Phospholane
742:Pyrrolidine
664:Heteroatom
659:heteroatom
648:dithiazoles
637:Dithiolanes
567:Diazetidine
515:Phosphetane
511:Phosphorus
470:Heteroatom
465:heteroatom
429:Oxaziridine
414:Diaziridine
376:episulfides
362:Phosphirene
357:Phosphirane
353:Phosphorus
290:Heteroatom
285:heteroatom
274:ring strain
3071:ChemSpider
3045:ChemSpider
3019:chemspider
3015:"Stibinin"
2830:References
2781:indigo dye
2363:Piperidine
2084:Heteroatom
2012:Saturated
1993:Borazocine
1934:Saturated
1914:Thiazepine
1885:Saturated
1806:Saturated
1735:Saturated
1686:Saturated
1637:Triazinane
1625:Saturated
1523:Morpholine
1495:Saturated
1470:Stanninane
1443:Tellurium
1348:not used)
1319:Pyridinium
1315:not used)
1298:Piperidine
1201:Saturated
1168:N N N N N
1158:N N N N S
1148:N N N N O
1130:Dithiazole
1094:Oxadiazole
1064:Saturated
1039:Dithiolane
1035:2× sulfur
1023:2× oxygen
1012:Thiazoline
932:Pyrazoline
890:Saturated
802:Selenolane
780:Phosphorus
710:Bismolane
680:Stibolane
667:Saturated
631:contain a
597:Dithietane
593:2× Sulfur
578:2× Oxygen
555:Saturated
473:Saturated
438:2× Oxygen
433:Oxazirine
402:Saturated
293:Saturated
164:piperidine
141:benzofuran
2754:uric acid
2730:phenalene
2714:carbazole
2702:quinoline
2698:isoindole
2394:Thiopyran
2307:Thiophene
2196:Azetidine
2117:Aziridine
2076:Saturated
2020:Nitrogen
1942:Nitrogen
1902:Diazepine
1897:Diazepane
1893:Nitrogen
1826:Nitrogen
1749:Pentazine
1743:Nitrogen
1700:Tetrazine
1694:Nitrogen
1664:Trithiane
1633:Nitrogen
1557:Oxathiane
1507:Diazinane
1447:Tellurane
1424:Thiopyran
1293:Nitrogen
1282:Germinane
1277:Germanium
1212:Antimony
1174:Pentazole
1142:Tetrazole
1118:Dioxazole
1078:Triazoles
1027:Dioxolane
989:Isoxazole
984:Oxazoline
952:Oxathiole
916:Imidazole
848:Tellurium
840:Thiophene
790:Phosphole
725:Borolane
695:Arsolane
625:Thiazoles
582:Dioxetane
520:Phosphete
485:Azetidine
481:Nitrogen
442:Dioxirane
419:Diazirine
318:Aziridine
314:Nitrogen
309:Borirene
153:carbazole
129:quinoline
113:thiophene
88:cellulose
3197:Category
3174:Archived
3041:"Bismin"
2988:(2007),
2928:25255204
2818:See also
2760:furfural
2718:acridine
2632:Thionine
2617:Thionane
2553:Thiocine
2538:Thiocane
2474:Thiepine
2459:Thiepane
2380:Pyridine
2287:Thiolane
2206:Thietane
2142:Thiirene
2127:Thiirane
2102:Nitrogen
2088:Nitrogen
2059:Thionine
2054:Thionane
1981:Thiocine
1976:Thiocane
1865:Thiepine
1860:Thiepane
1772:Borazine
1768:hexazine
1652:Trioxane
1642:Triazine
1588:Dithiane
1563:Oxathiin
1546:Thiazine
1475:Stannine
1403:Silinane
1380:Selenane
1375:Selenium
1352:Pyrylium
1307:Pyridine
1264:Borinine
1259:Borinane
1233:Arsinine
1228:Arsinane
1224:Arsenic
1218:Stibinin
1136:N N N N
1044:Dithiole
1008:Thiazole
927:Pyrazole
870:Stannole
797:Selenium
736:Nitrogen
676:Antimony
602:Dithiete
530:Thietane
382:Thiirene
372:Thiirane
341:epoxides
305:Borirane
188:borazine
145:acridine
109:pyridine
96:nitrogen
61:elements
41:Pyridine
3102:Bibcode
3077:11 June
3051:11 June
3025:11 June
2799:purines
2774:pyrrole
2750:alloxan
2627:Oxonine
2622:Azonine
2612:Oxonane
2607:Azonane
2548:Oxocine
2543:Azocine
2533:Oxocane
2528:Azocane
2469:Oxepine
2464:Azepine
2454:Oxepane
2449:Azepane
2293:Pyrrole
2282:Oxolane
2201:Oxetane
2137:Oxirene
2132:Azirine
2122:Oxirane
2108:Sulfur
2050:Sulfur
2044:Oxonine
2039:Oxonane
2035:Oxygen
2029:Azonine
2024:Azonane
1972:Sulfur
1966:Oxocine
1961:Oxocane
1957:Oxygen
1951:Azocine
1946:Azocane
1856:Sulfur
1850:Oxepine
1845:Oxepane
1841:Oxygen
1835:Azepine
1830:Azepane
1820:Borepin
1660:Sulfur
1648:Oxygen
1593:Dithiin
1578:Dioxine
1573:Dioxane
1529:Oxazine
1512:Diazine
1459:cation
1438:cation
1414:Sulfur
1398:Silicon
1392:cation
1354:cation
1326:Oxygen
1321:cation
1287:Germine
1240:Bismuth
1090:Furazan
980:Oxazole
814:Silicon
750:Pyrrole
714:Bismole
706:Bismuth
691:Arsenic
684:Stibole
587:Dioxete
572:Diazete
526:Sulfur
500:Oxetane
496:Oxygen
368:Sulfur
347:Oxirene
333:Oxirane
329:Oxygen
323:Azirine
261:isomers
198:ring),
117:pyrrole
84:biomass
2998:
2926:
2865:
2793:1951:
2788:Treibs
2786:1936:
2764:starch
2694:indole
2374:Thiane
2221:Thiete
2105:Oxygen
2098:Sulfur
2093:Oxygen
1814:Boron
1418:Thiane
1408:Siline
1271:anion
1247:Bismin
1124:N S S
1112:N O O
1100:N N S
1084:N N O
1072:N N N
829:Sulfur
822:Silole
759:Oxygen
729:Borole
699:Arsole
633:sulfur
621:azoles
535:Thiete
301:Boron
243:atoms.
241:carbon
176:ethers
172:amines
155:, and
139:, and
137:indole
119:, and
2955:IUPAC
2766:with
2752:from
2387:Pyran
2369:Oxane
2300:Furan
2216:Oxete
2211:Azete
1708:boron
1615:three
1346:Oxine
1336:Pyran
1330:Oxane
1313:Azine
1254:Boron
1207:Ions
1054:three
772:Furan
721:Boron
644:three
505:Oxete
490:Azete
248:IUPAC
224:IUPAC
121:furan
55:is a
3144:2010
3079:2018
3053:2018
3027:2018
2996:ISBN
2942:link
2924:PMID
2863:ISBN
2810:Uses
2801:and
1762:The
1725:five
1676:four
627:and
174:and
166:and
3110:doi
2969:doi
2967:".
2916:doi
2889:doi
2704:or
2696:or
1875:two
1796:one
1770:.
1485:two
1465:Tin
1191:one
880:two
862:Tin
657:one
623:.
617:two
545:two
463:one
392:two
283:one
92:FDA
51:or
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3185:,
3130:.
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3017:.
2957:,
2938:}}
2934:{{
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2885:29
2883:.
2854:^
2732:.
2716:,
1428:(2
1340:(2
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343:)
339:,
202:(P
190:(B
151:,
147:,
135:,
131:,
115:,
111:,
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47:A
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220:4
218:N
216:4
214:S
208:3
206:N
204:3
196:3
194:N
192:3
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