742:
349:
230:
28:
757:
37:
522:
65:
527:
810:
966:
915:
56:
655:
1170:
Roy, Ranabir Sinha; Gehring, Amy M.; Milne, Jill C.; Belshaw, Peter J.; Walsh, Christopher T.; Roy, Ranabir Sinha; Gehring, Amy M.; Milne, Jill C.; Belshaw, Peter J.; Walsh, Christopher T. (1999). "Thiazole and
Oxazole Peptides: Biosynthesis and Molecular Machinery".
535:
502:
609:
668:
605:
1208:
1075:
1206:
GĂ©rard Moine; Hans-Peter
Hohmann; Roland Kurth; Joachim Paust; Wolfgang HĂ€hnlein; Horst Pauling; BerndâJĂŒrgen Weimann; Bruno Kaesler (2011). "Vitamins, 6. B Vitamins".
741:
398:
1114:
Zoltewicz, J. A. & Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978).
573:
1225:
1099:
975:
three equivalents of water are consumed for each equivalent of oxazoline, generating 4 protons and 4 electrons (the latter derived from Ce).
876:
886:
1154:
363:
735:
1282:
756:
601:
675:
567:
306:
327:
1083:
479:
965:
750:
237:
892:
585:
267:
521:
1124:
932:
880:
597:
526:
225:
948:
936:
187:
593:
691:
549:
514:
273:
83:
344:
773:
637:
101:
581:
861:
of oxazoles occurs at C2, and the lithio salt exists in equilibrium with the ring-opened enolate-
621:
147:
853:
of 0.8 for the conjugate acid (oxazolium salts), oxazoles are far less basic than imidazoles (pK
135:
900:
1277:
1221:
1188:
1150:
1095:
944:
895:
involving oxazole (as dienes) and electrophilic alkenes has been well developed as a route to
870:
705:
1255:
1213:
1180:
1087:
1051:
697:
617:
421:
947:
reactions. One study reports on the oxidation of 4,5-diphenyloxazole with 3 equivalents of
315:
256:
207:
27:
111:
809:
348:
229:
167:
1241:
709:
646:
914:
1271:
1039:
972:
908:
858:
469:
218:
625:
64:
956:
789:
36:
555:
1080:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
295:
1016:
1004:
834:
55:
1246:
1043:
923:
919:
904:
866:
862:
765:
577:
449:
198:
1217:
1022:
1010:
985:
797:
769:
723:
589:
1192:
613:
1091:
939:
with the organic acyl residue and the C5 substituent changing positions.
998:
989:
896:
838:
801:
694:
559:
911:
affords a bicyclic intermediate, with an acid-sensitive oxo bridgehead.
1036:
Fully
Automated Continuous Flow Synthesis of 4,5-Disubstituted Oxazoles
827:(1) Enzymatic cyclization. (2) Elimination. (3) = enzymatic oxidation.
459:
282:
238:
1259:
1055:
899:. In this way, alkoxy-substituted oxazoles serve a precursors to the
1184:
793:
777:
704:
with an oxygen and a nitrogen separated by one carbon. Oxazoles are
178:
645:
Except where otherwise noted, data are given for materials in their
952:
913:
808:
701:
158:
134:
124:
992:
713:
755:
740:
708:
but less so than the thiazoles. Oxazole is a weak base; its
332:
63:
54:
35:
26:
1240:"Ceric Ammonium Nitrate Promoted Oxidation of Oxazoles",
792:, oxazoles result from the cyclization and oxidation of
663:
918:
Use of an oxazole in the synthesis of a precursor to
753:
from cyanohydrins and aldehydes is also widely used:
764:
Other methods are known including the reaction of α-
1076:International Union of Pure and Applied Chemistry
1001:, an analog with the oxygen replaced by a sulfur.
825:for serine and threonine respectively, B = base.
294:
1042:, Christoper D. Smith, and Geoffrey K. Tranmer
1007:, where the oxazole is fused to a benzene ring.
110:
1209:Ullmann's Encyclopedia of Industrial Chemistry
8:
690:is the parent compound for a vast class of
474:69.5 °C (157.1 °F; 342.6 K)
347:
228:
206:
15:
314:
1067:
889:takes place with leaving groups at C2.
841:with oxygen replaced by a sulfur atom.
403:
368:
343:
272:
1019:, which has both double bonds reduced.
738:by dehydration of 2-acylaminoketones:
219:
1140:
1138:
375:Key: ZCQWOFVYLHDMMC-UHFFFAOYSA-N
186:
166:
7:
1013:, which has one double bond reduced.
877:Electrophilic aromatic substitution
385:Key: ZCQWOFVYLHDMMC-UHFFFAOYAD
285:
1038:Marcus Baumann, Ian R. Baxendale,
887:Nucleophilic aromatic substitution
372:InChI=1S/C3H3NO/c1-2-5-3-4-1/h1-3H
14:
1254:; 8(24) pp 5669 - 5671; (Letter)
1244:, Pavel Nagorny, and Risheng Xu.
1025:, an analog with a carbonyl group
879:takes place at C5, but requiring
382:InChI=1/C3H3NO/c1-2-5-3-4-1/h1-3H
964:
833:Oxazoles are not as abundant in
734:The classic synthetic route the
653:
525:
520:
439:
433:
935:of 4-acyloxazoles is a thermal
649:(at 25 °C , 100 kPa).
1084:The Royal Society of Chemistry
745:The RobinsonâGabriel synthesis
442:
427:
1:
50:
22:
1299:
865:, which can be trapped by
736:RobinsonâGabriel synthesis
722:of 0.8, compared to 7 for
873:gives 2-formyloxazole.
760:Fischer Oxazole Synthesis
751:Fischer oxazole synthesis
643:
636:
631:
501:
496:
454:69.06 g/mol
414:
394:
359:
94:
82:
77:
49:
21:
1218:10.1002/14356007.o27_o09
1145:T. L. Gilchrist (1997).
1129:pubchem.ncbi.nlm.nih.gov
1050:; 8(23) pp 5231 - 5234.
922:, which is converted to
881:electron donating groups
632:Supplementary data page
568:Precautionary statements
492:0.8 (of conjugate acid)
1212:. Weinheim: Wiley-VCH.
1173:Natural Product Reports
1149:(3 ed.). Longman.
933:Cornforth rearrangement
1147:Heterocyclic Chemistry
937:rearrangement reaction
927:
828:
761:
746:
68:
59:
40:
31:
1283:Simple aromatic rings
1092:10.1039/9781849733069
988:, an analog with the
951:to the corresponding
917:
893:DielsâAlder reactions
812:
759:
744:
67:
58:
39:
30:
903:system, as found in
869:. Formylation with
84:Preferred IUPAC name
776:with aldehydes and
774:Van Leusen reaction
638:Oxazole (data page)
148:Beilstein Reference
18:
1030:Additional reading
928:
829:
762:
747:
706:aromatic compounds
676:Infobox references
69:
60:
41:
32:
16:
1260:10.1021/ol0624530
1227:978-3-527-30673-2
1101:978-0-85404-182-4
1056:10.1021/ol061975c
871:dimethylformamide
698:organic compounds
684:Chemical compound
682:
681:
550:Hazard statements
328:CompTox Dashboard
136:Interactive image
73:
72:
45:
44:
1290:
1262:
1238:
1232:
1231:
1203:
1197:
1196:
1185:10.1039/A806930A
1167:
1161:
1160:
1142:
1133:
1132:
1121:
1115:
1112:
1106:
1105:
1072:
971:In the balanced
968:
824:
823:
822:
666:
660:
657:
656:
627:
623:
619:
615:
611:
607:
603:
599:
595:
591:
587:
583:
579:
575:
561:
557:
529:
524:
444:
441:
435:
429:
422:Chemical formula
352:
351:
336:
334:
318:
298:
287:
276:
257:Gmelin Reference
240:
232:
221:
210:
190:
170:
138:
114:
51:
23:
19:
1298:
1297:
1293:
1292:
1291:
1289:
1288:
1287:
1268:
1267:
1266:
1265:
1239:
1235:
1228:
1205:
1204:
1200:
1169:
1168:
1164:
1157:
1144:
1143:
1136:
1123:
1122:
1118:
1113:
1109:
1102:
1086:. p. 140.
1074:
1073:
1069:
1064:
1032:
982:
930:
907:. The initial
856:
852:
847:
837:as the related
826:
821:
818:
817:
816:
814:
786:
732:
720:
685:
678:
673:
672:
671: ?)
662:
658:
654:
650:
570:
552:
538:
517:
488:
438:
432:
424:
410:
407:
402:
401:
390:
387:
386:
383:
377:
376:
373:
367:
366:
355:
337:
330:
321:
301:
288:
259:
250:
213:
193:
173:
150:
141:
128:
117:
104:
90:
89:
12:
11:
5:
1296:
1294:
1286:
1285:
1280:
1270:
1269:
1264:
1263:
1242:David A. Evans
1233:
1226:
1198:
1179:(2): 249â263.
1162:
1155:
1134:
1116:
1107:
1100:
1066:
1065:
1063:
1060:
1059:
1058:
1031:
1028:
1027:
1026:
1020:
1014:
1008:
1002:
996:
995:in position 2.
981:
978:
977:
976:
969:
961:
960:
854:
850:
846:
843:
831:
830:
819:
785:
782:
731:
728:
718:
710:conjugate acid
683:
680:
679:
674:
652:
651:
647:standard state
644:
641:
640:
634:
633:
629:
628:
610:P305+P354+P338
606:P303+P361+P353
571:
566:
563:
562:
553:
548:
545:
544:
539:
534:
531:
530:
518:
513:
510:
509:
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362:
361:
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345:DTXSID70182983
340:
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326:
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322:
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311:
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303:
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291:
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183:
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155:
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146:
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119:
118:
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107:
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100:
97:
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71:
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61:
47:
46:
43:
42:
33:
13:
10:
9:
6:
4:
3:
2:
1295:
1284:
1281:
1279:
1276:
1275:
1273:
1261:
1257:
1253:
1249:
1248:
1243:
1237:
1234:
1229:
1223:
1219:
1215:
1211:
1210:
1202:
1199:
1194:
1190:
1186:
1182:
1178:
1174:
1166:
1163:
1158:
1156:0-582-01421-2
1152:
1148:
1141:
1139:
1135:
1130:
1126:
1120:
1117:
1111:
1108:
1103:
1097:
1093:
1089:
1085:
1081:
1077:
1071:
1068:
1061:
1057:
1053:
1049:
1045:
1041:
1040:Steven V. Ley
1037:
1034:
1033:
1029:
1024:
1021:
1018:
1015:
1012:
1009:
1006:
1003:
1000:
997:
994:
991:
987:
984:
983:
979:
974:
973:half-reaction
970:
967:
963:
962:
958:
954:
950:
946:
942:
941:
940:
938:
934:
925:
921:
916:
912:
910:
909:cycloaddition
906:
902:
898:
894:
890:
888:
884:
882:
878:
874:
872:
868:
864:
860:
859:Deprotonation
844:
842:
840:
836:
813:Where X = H,
811:
807:
806:
805:
803:
800:nonribosomal
799:
795:
791:
783:
781:
779:
775:
771:
767:
758:
754:
752:
743:
739:
737:
729:
727:
725:
721:
717:
711:
707:
703:
700:. These are
699:
696:
693:
689:
677:
670:
665:
648:
642:
639:
635:
630:
572:
569:
565:
564:
554:
551:
547:
546:
543:
540:
537:
533:
532:
528:
523:
519:
516:
512:
511:
507:
505:
500:
495:
491:
485:
481:
478:
477:
473:
471:
470:Boiling point
468:
467:
463:
461:
458:
457:
453:
451:
448:
447:
426:
423:
419:
418:
413:
404:
400:
393:
379:
369:
365:
358:
350:
346:
342:
341:
339:
329:
325:
324:
317:
313:
312:
310:
308:
305:
304:
297:
293:
292:
290:
284:
280:
279:
275:
271:
269:
266:
265:
261:
258:
254:
253:
246:
245:
243:
241:
236:
235:
231:
227:
224:
222:
220:ECHA InfoCard
217:
216:
209:
205:
204:
202:
200:
197:
196:
189:
188:ChEMBL2171710
185:
184:
182:
180:
177:
176:
169:
165:
164:
162:
160:
157:
156:
152:
149:
145:
144:
137:
133:
132:
130:
126:
121:
120:
113:
109:
108:
106:
103:
99:
98:
93:
85:
81:
76:
66:
62:
57:
53:
52:
48:
38:
34:
29:
25:
24:
20:
1251:
1245:
1236:
1207:
1201:
1176:
1172:
1165:
1146:
1128:
1119:
1110:
1079:
1070:
1047:
1035:
957:benzoic acid
929:
891:
885:
875:
848:
835:biomolecules
832:
790:biomolecules
787:
784:Biosynthesis
763:
748:
733:
715:
692:heterocyclic
687:
686:
541:
503:
483:
95:Identifiers
1017:Oxazolidine
1005:Benzoxazole
766:haloketones
730:Preparation
536:Signal word
464:1.050 g/cm
415:Properties
226:100.005.474
168:CHEBI:35597
88:1,3-Oxazole
1272:Categories
1247:Org. Lett.
1062:References
1044:Org. Lett.
924:vitamin B6
920:pyridoxine
905:vitamin B6
867:silylation
863:isonitrile
515:Pictograms
450:Molar mass
316:FJZ20I1LPS
199:ChemSpider
123:3D model (
102:CAS Number
1125:"Oxazole"
1023:Oxazolone
1011:Oxazoline
986:Isoxazole
945:oxidation
901:pyridoxyl
897:pyridines
849:With a pK
845:Reactions
839:thiazoles
798:threonine
770:formamide
724:imidazole
622:P403+P235
618:P370+P378
598:P264+P265
506:labelling
406:C1=COC=N1
247:206-020-8
239:EC Number
1278:Oxazoles
1193:10331285
1078:(2014).
999:Thiazole
990:nitrogen
980:See also
943:Various
802:peptides
772:and the
695:aromatic
497:Hazards
112:288-42-6
17:Oxazole
931:In the
688:Oxazole
669:what is
667: (
480:Acidity
460:Density
283:PubChem
274:D010080
262:485850
153:103851
1224:
1191:
1153:
1098:
857:= 7).
794:serine
778:TosMIC
712:has a
702:azoles
664:verify
661:
542:Danger
399:SMILES
179:ChEMBL
78:Names
953:imide
364:InChI
159:ChEBI
125:JSmol
1252:2006
1222:ISBN
1189:PMID
1151:ISBN
1096:ISBN
1048:2006
993:atom
955:and
768:and
749:The
626:P501
614:P317
602:P280
594:P243
590:P242
586:P241
582:P240
578:P233
574:P210
560:H318
556:H225
307:UNII
296:9255
268:MeSH
208:8898
1256:doi
1214:doi
1181:doi
1088:doi
1052:doi
949:CAN
796:or
788:In
504:GHS
333:EPA
286:CID
1274::
1250:;
1220:.
1187:.
1177:16
1175:.
1137:^
1127:.
1094:.
1082:.
1046:;
883:.
815:CH
804::
780:.
726:.
624:,
620:,
616:,
612:,
608:,
604:,
600:,
596:,
592:,
588:,
584:,
580:,
576:,
558:,
508::
489:)
482:(p
1258::
1230:.
1216::
1195:.
1183::
1159:.
1131:.
1104:.
1090::
1054::
959::
926:.
855:a
851:a
820:3
719:a
716:K
714:p
659:N
487:a
484:K
443:O
440:N
437:3
434:H
431:3
428:C
335:)
331:(
127:)
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