Aliphatic ß-chlorovinylaldehydes as versatile building blocks in syntheses of heterocycles

Aliphatic ß-chlorovinylaldehydes are readily prepared from alkyl methyl ketones using Vilsmeier-Haack-Arnold reaction.

A survey of the literature often shows complex reactions by great expending time and resources for getting aliphatic substituted heterocycles. On the other hand such compounds can easily synthesize from ß-chlorovinylaldehydes by reaction with O-, N- and S-nucleophiles. So we synthesized a variety of heterocyclic systems like isothiazoles, pyrazoles, quinolines, isoxazoles, thiophenes and pyrimidines.

A survey of the literature let us expect that these compounds have a broad spectrum of useful biologically activity. It is of interest that aliphatic ß-chlorovinylaldehydes show a different reaction behavior compared with those described in the literature. In this poster we will report experimental details on syntheses and spectroscopic studies of the described compounds.