UNEXPECTED PRODUCT FROM THE DAKIN-WEST REACTION OF N-ACYLPROLINES USING TRIFLUOROACETIC-ANHYDRIDE - A NOVEL ACCESS TO 5-TRIFLUOROMETHYLOXAZOLES

被引：22

作者：

KAWASE, M ^{[1
]}

MIYAMAE, H ^{[1
]}

NARITA, M ^{[1
]}

KURIHARA, T ^{[1
]}

机构：

[1] JOSAI UNIV,FAC SCI,SAKADO,SAITAMA 35002,JAPAN

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 05期

关键词：

N-ACYLPROLINE; OXAZOLE; TRIFLUOROMETHYL; TRIFLUOROACETIC ANHYDRIDE; REARRANGEMENT;

D O I：

10.1016/0040-4039(93)89032-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The base-catalyzed reaction of N-acylprolines with trifluoroacetic anhydride proceeds through mesoionic 1,3-oxazolium-5-olates followed by the pyrrolidine ring cleavage to afford the 5-trifluoromethyloxazoles in good yields.

引用

页码：859 / 862

页数：4

共 10 条

[1] SOME KINETIC AND MECHANISTIC STUDIES OF DAKIN-WEST REACTION [J].

ALLINGER, NL ;

WANG, GL ;

DEWHURST, BB .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (12) :1730-1735

[2] PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES [J].

BEGUE, JP ;

BONNETDELPON, D .

TETRAHEDRON, 1991, 47 (20-21) :3207-3258

[3]

BOYD GV, 1984, COMPREHENSIVE HETERO, V6, pCH18

[4] THE DAKIN-WEST REACTION [J].

BUCHANAN, GL .

CHEMICAL SOCIETY REVIEWS, 1988, 17 (02) :91-109

[5] SYNTHESIS OF POTENTIAL SPECIFIC INHIBITORS OF CERTAIN AMINO-ACID DECARBOXYLASES [J].

ISRAILI, ZH ;

SMISSMAN, EE .

JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1977, 22 (03) :357-359

[6]

KAWSE M, 1992, J CHEM SOC CHEM COMM, P1076

[7] TRIFLUOROMETHYLATIONS AND RELATED REACTIONS IN ORGANIC-CHEMISTRY [J].

MCCLINTON, MA ;

MCCLINTON, DA .

TETRAHEDRON, 1992, 48 (32) :6555-6666

[8]

Silvester M. J., 1991, ALDRICHIM ACTA, V24, P31

[9]

TUCHI IJ, 1986, CHEM HETEROCYCLIC CO, V45

[10]

WASSERMAN HH, 1987, J CHEM SOC CHEM COMM, V47, P300

← 1 →