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.

scheme 1

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.

scheme 2

A survey of the literature let us expect that these compounds have a broad spectrum of useful biologically activity. With this research we look for new applications of fatty renewable materials in the matter of fine chemicals. It is also of interest that aliphatic
ß-chlorovinylaldehydes show a different reaction behavior compared with those described in the literature.