Reactions of 1,2-diaza-1,3-dienes with thiol derivatives: a versatile construction of nitrogen/sulfur containing heterocycles

摘要

The synthesis of substituted 2,3-dihydro-1,4-thiazines, fused cycloalkyl-1,4-thiazines, 1.4-benzothiazines and fused cycloalkyl-1,4-benzothiazines by 1,4-addition of 1,2-animothiols to 1.2-diaza-13-clienes bearing carboxylate, carboxamide, or phosphorylated groups and subsequent internal heterocyclization is described. The reaction of carboxylated 1,2-diaza-1,3-butadienes with 2-(butylamino)ethanethiol affords 1,4-thiazinan-3-ones. The solid-phase reaction of polymer-bound 1,2-diaza-1,3-butadienes with 1,2-aminothiols produces 2,3-dihydro-1,4-thiazines and 1,4-benzothiazines. (C) 2008 Elsevier Ltd. All rights reserved.