Base catalysed synthesis of thiochromans and azo-linked chromenes using allenylphosphonates

Abstract

An efficient base catalysed approach to the synthesis of thiochromans/chromenes from allenylphosphonates (and an allenoate) and substrates having SH/OH and CHO groups at appropriate positions has been developed. Several azo-linked chromenes that are bright red pigments are also synthesized. This methodology involves the domino reactions of Michael addition and subsequent cyclisation by intramolecular aldol reaction. © 2012 The Royal Society of Chemistry.