The para-toluenesulfonic acid-promoted synthesis of 2-substituted benzoxazoles and benzimidazoles from diacylated precursors.

被引：63

作者：

DeLuca, MR ^{[1
]}

Kerwin, SM ^{[1
]}

机构：

[1] UNIV TEXAS,COLL PHARM,DIV MED CHEM,AUSTIN,TX 78712

来源：

TETRAHEDRON | 1997年 / 53卷 / 02期

关键词：

D O I：

10.1016/S0040-4020(96)01009-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of benzoxazoles and benzimidazoles is accomplished by treating N,O-diacylated 2-aminophenols or N,N'-diacylated 1,2-phenylenediamines with p-toluenesulfonic acid under reflux in xylenes or toluene. These reactions are operationally simple and proceed in excellent yield. Copyright (C) 1996 Elsevier Science Ltd

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页码：457 / 464

页数：8

相关论文

共 29 条

[1] AN EFFICIENT SYNTHESIS OF 2-VINYLBENZIMIDAZOLES FROM 1-(2-BENZIMIDAZOL-2-YLETHYL)PYRIDINIUM SALTS USING AN ANION-EXCHANGE RESIN [J].

ALCALDE, E ;

PEREZGARCIA, L ;

DINARES, I ;

FRIGOLA, J .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6516-6521

[2] A MECHANISTIC STUDY OF 2-VINYLBENZIMIDAZOLE FORMATION FROM 2-(2'-HALOETHYL)BENZIMIDAZOLES - SYNTHESIS OF HIGHLY ELECTRON-RICH VINYLIC COMPOUNDS BY GENERAL BASE AND SPECIFIC ACID-GENERAL BASE CATALYSIS [J].

BORUAH, RC ;

SKIBO, EB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) :7797-7803

[3]

Cassidy PE, 1980, THERMALLY STABLE POL

[4] POTENTIAL ANTITUMOR AGENTS .59. STRUCTURE-ACTIVITY-RELATIONSHIPS FOR 2-PHENYLBENZIMIDAZOLE-4-CARBOXAMIDES, A NEW CLASS OF MINIMAL DNA-INTERCALATING AGENTS WHICH MAY NOT ACT VIA TOPOISOMERASE-II [J].

DENNY, WA ;

REWCASTLE, GW ;

BAGULEY, BC .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (02) :814-819

[5]

FRACHAY G, 1994, HETEROCYCLES, V38, P2621

[6] SYNTHESIS AND APPLICATIONS OF ORGANIC POLYMERS AS SUPPORTS AND PROTECTING GROUPS [J].

FRECHET, JMJ .

TETRAHEDRON, 1981, 37 (04) :663-683

[7] REEXAMINATION OF THE THERMOLYTIC REARRANGEMENT OF 4-HALOPHENYL AZIDES TO 2-AMINOPHENOLS AND OTHER PRODUCTS [J].

GERSHON, H ;

CLARKE, DD ;

GERSHON, M .

MONATSHEFTE FUR CHEMIE, 1993, 124 (04) :367-379

[8]

Goker H, 1995, J HETEROCYCLIC CHEM, V32, P1767

[9] FORMATION OF BENZIMIDAZOLES AT HIGH-PRESSURE [J].

HOLAN, G ;

EVANS, JJ ;

LINTON, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (10) :1200-1203

[10]

JARRAR AA, 1978, J HETEROCYCLIC CHEM, V15, P171