Diversity in Synthesis of N-Heterocycles from Simple Propargylic Alcohols

Abstract

In this account, we summarize our recent work on the preparation of various N-heterocycles, starting from propargylic alcohols. Our aim was to develop versatile and selective one-pot procedures that would permit the synthesis of large collections of heterocycles, such as di- or tri-substituted isoxazolines and isoxazoles, <i>cis</i>-aziridines, and pyrimidines, by fine changes in the reaction conditions. When needed, mechanistic studies have been performed by combining experimental work with density functional theory calculations. 1 Introduction 2 Synthesis of Disubstituted Isoxazolines 3 Synthesis of Disubstituted Isoxazoles 4 Synthesis of <i>cis-</i>Acylaziridines 5 Trisubstituted Isoxazolines and Isoxazoles 6 β-Enaminones and Pyrimidines 7 Conclusion