通过异氰化物的多组分反应合成1,4-噻氮杂䓬、1,4-苯并噻氮杂䓬-5-酮和1,4-苯并噻氧杂䓬原酰胺。

1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides.

作者信息

Marcaccini Stefano, Miguel Daniel, Torroba Tomás, García-Valverde María

机构信息

Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, 50019-Sesto Fiorentino, Florence, Italy.

出版信息

J Org Chem. 2003 Apr 18;68(8):3315-8. doi: 10.1021/jo026614z.

DOI:10.1021/jo026614z

PMID:12688810

Abstract

The intramolecular Ugi four-component condensation between 6-oxo-4-thiacarboxylic acids, benzylamines, and cyclohexyl isocyanide gave hexahydro-1,4-thiazepin-5-ones and 1,4-benzothiazepin-5-ones, in some cases with high stereoselectivity, and the intramolecular Passerini three-component reaction, in the presence of catalytic amine, gave tetracyclic 1,4-benzothioxepin orthoamides.

摘要

6-氧代-4-硫代羧酸、苄胺和环己基异氰化物之间的分子内Ugi四组分缩合反应生成了六氢-1,4-噻氮平-5-酮和1,4-苯并噻氮平-5-酮，在某些情况下具有高立体选择性，并且在催化胺存在下的分子内Passerini三组分反应生成了四环1,4-苯并噻硫平原酸酯。