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Review | Regular issue | Vol 87, No. 5, 2013, pp.967-990
Published online, 25th March, 2013
DOI: 10.3987/REV-13-765
■ The Pseudo-Intramolecular Process: A Novel Synthetic Method for Functionalized Heterocyclic Compounds

Nagatoshi Nishiwaki*

*School of Science and Technology, Kochi University of Technology, Tosayamada-cho, Kochi, 782-8502, Japan

Abstract

A pseudo-intramolecular process has been developed. Compounds having both an acidic hydrogen and a functionality serve as substrates in the present method, and immediately form an ammonium salt after the addition of an amine. When the amine is liberated under mild equilibrium conditions, both the nucleophilic amine and the electrophilic substrate are in proximity and efficiently react under mild reaction conditions. Although the reaction actually concerns an intermolecular process, it proceeds as if it were an intramolecular process. Thus, this method forms a novel procedure for synthesizing polyfunctionalized compounds that are not easily available via alternative methods.