From a three-component synthesis to multistep cascade reactions. Twenty years in the chemistry of N-(1-haloalkyl)azinium halides

Abstract

N-(1-Haloalkyl)azinium halides are readily available through a three-component reaction of an azine, an aldehyde, and a thionyl halide. Those salts represent activated forms of the starting aldehydes and can be used advantageously for the preparation of other azinium salts, imines, 1,1-diamines, and a wide range of nitrogen (fused) heterocycles. Recently it has also been demonstrated that N-(1-haloalkyl)azinium halides can be transformed into bis(1,3,4-thiadiazolo)-1,3,5-triazinium halides, a novel class of versatile tricyclic systems that exhibits many useful synthetic potentialities. ©ARKAT-USA, Inc.