Design and development of new synthetic methods for biologically important five membered heterocycles via novel organosulfur synthons

Abstract

The α-oxoketene dithioacetals are generally crystalline solids or distillable liquids and exhibit prolonged shelf-life. They are stable at room temperature and reasonably stable to mild acidic and basic conditions. On the other hand, the corresponding O,Oacetals B are moisture sensitive and are susceptible for hydrolysis even under mild conditions. Although few of α-oxoketene dithioacetals were reported in 19102 and later on by Thuillier and co-workers,3 no systematic investigation on the reactivity and synthetic applications of these versatile synthons was undertaken until mid 1970’s when Junjappa and Ila’s group extensively explored the synthetic utility of these compounds and developed new general methods for various heterocycles and carbocycles based on these intermediates. This work has been highlighted in several reviews.1