Synthesis of novel heterocyclic calixarenes via the Diels-Alder reaction of calix[4]bis(spirodienones)

Abstract

The reactivity of calix[4]bis(spirodienones) depends on the nature of the dienophile used. With 1,4-benzoquinones it acts as a 4 pi component whereas with 1,2-benzoquinones as a 2 pi system, yielding benzodioxin derived macrocycles in good yield. Bis(spirodienones) can thus perform as a diene as well as a dienophile in cycloaddition reactions.