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, cis-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 cis-Acylaziridines

5 Trisubstituted Isoxazolines and Isoxazoles

6 β-Enaminones and Pyrimidines

7 Conclusion

Key words

iron - palladium - heterocycles - isomerization - ring closure - catalysis

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