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■ Copper Catalyzed Cyclopropanation of 1,2,3,4-Tetrahydropyridin-2-ones with Trimethylsilyldiazomethane: A Facile and Selective Synthesis of 2-Aza-3-oxobicyclo[4.1.0]heptanes

Vishal B. Sharma, Suman L. Jain, and Bir Sain*

*Chemical and Biotechnology Division, Indian Institute of Petroleum, Dehradun-248005, India

Abstract

The reactions of a series of 1,2,3,4-tetrahydropyridin-2-ones with trimethylsilyldiazomethane using catalytic amounts of copper(II) triflate in refluxing 1,2-dichloroethane yielded exclusively 3-oxo-2-azabicyclo[4.1.0]heptanes in good yields. The application of ultrasonic radiation enhanced the reaction rate and allowed the reactions to be conducted at room temperature.