Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction

Abstract

We have recently reported a novel multicomponent reaction between arylacetic acids and isocyanides, affording α-acyloxyacrylamides through an unusual mechanism. The products of this novel multicomponent reaction can rearrange to five membered heterocyclic compounds when exposed to an alkaline environment. Depending on the reaction conditions and on the substitution pattern on the substrates, various pyrrolidine derivatives can be selectively obtained. We now wish to report that libraries endowed with skeletal diversity, thus responding to the requirements of Diversity Oriented Synthesis (DOS), can be efficiently prepared in this manner, and phenotypic biological assays have shown interesting properties of some representative compounds.

Keywords

• multicomponent reactions
• isocyanides
• rearrangement reactions
• diversity oriented synthesis