CARBOHYDRATE-DERIVED MESIONIC COMPOUNDS .1. SYNTHESIS AND REACTIVITY TOWARD ACETYLENIC DIPOLAROPHILES OF IMIDAZO(2,1-B)THIAZOLIUM-3-OLATE SYSTEMS

被引：21

作者：

ARECES, P ^{[1
]}

AVALOS, M ^{[1
]}

BABIANO, R ^{[1
]}

GONZALEZ, L ^{[1
]}

JIMENEZ, JL ^{[1
]}

PALACIOS, JC ^{[1
]}

PILO, MD ^{[1
]}

机构：

[1] UNIV EXTREMADURA,DEPT ORGAN CHEM,E-06071 BADAJOZ,SPAIN

来源：

CARBOHYDRATE RESEARCH | 1991年 / 222卷

关键词：

D O I：

10.1016/0008-6215(91)89009-5

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The reaction of 1-phenyl-(3,5,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucofurano)[2,1-d]imidazolidine-2-thione (1) with alpha-bromophenylacetic acid and cyclisation with acetic anhydride-triethylamine of the thioglycolic acid intermediate led to the mesoionic derivative 2,5-diphenyl-(3,5,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucofurano)[1',2':4,5]-4aH,4bH-imidazo[2,1-b]thiazolium-3-olate (5). Likewise, 7-(4-ethoxyphenyl)-2-phenyl-5-(1,2,3,4-tetra-O-acetyl-D-arabino-tetriol-1-yl)imidazo[2,1-b)]thiazolium-3-olate (9) was obtained from 1-(4-ethoxyphenyl)-4-(1,2,3,4-tetra-O-acetyl-D-arabino-tetritol-1-yl)imidazoline-2-thione(6).The 1.3-dipolar cycloadditions of 5 and 9 with several acetylenic dipolarophiles gave the corresponding imidazo[1,2-a]pyridin-4-ones. With unsymmetrical dipolarophiles, these reactions were highly regioselective and only one regioisomer was isolated.

引用

页码：99 / 112

页数：14

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