Nucleophilic intramolecular cyclization reactions of alkynechalcogenolates

被引：51

作者：

Abramov, MA

Dehaen, W

D'hooge, B

Petrov, ML

Smeets, S

Toppet, S

Voets, M

机构：

[1] Univ Louvain, Dept Chem, B-3001 Heverlee, Belgium

[2] St Petersburg State Inst Technol, St Petersburg 198013, Russia

来源：

TETRAHEDRON | 2000年 / 56卷 / 24期

关键词：

heterocycles; thiadiazoles; ring opening; cyclization; benzofurans; indoles;

D O I：

10.1016/S0040-4020(00)00315-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(ortho-Hydroxyphenyl)-alkynethiolates and -selenolates, obtained through base catalyzed ring cleavage of 4-(ortho-hydroxy phenyl)-1,2,3-thiadiazoles and -1,2,3-selenadiazoles, smoothly transform into 2-benzofuranthiolates and -selenolates. These reactive intermediates can be alkylated in high yield. This reaction sequence could be applied to the synthesis of electron rich thiacrown ethers. The 2-(ortho-aminophenyl)-alkynethiolate analogously forms 2-methylsulfanylindole. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3933 / 3940

页数：8

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