A High-Yielding General Synthesis of α-Lactams [1]

Abstract

A high-yielding general synthesis of α-lactams (aziridinones) is described. An α-haloamide 1 precursor is cyclized by sodium hydride in the presence of 15-crown-5 ether at room temperature, using dichloromethane as the solvent. The by-products, hydrogen gas and sodium halide, are easily removed. The yields for the six known α-lactams (2b-g) chosen for this study are comparable or superior to previously reported yields, [6] [7] [11] [19-21] yet only short reaction times and a simple work-up is required.

Key words

aziridinones - dehydrohalogenation - heterocycles - ring closure

1

Part of this work was presented at the 223^rd National Meeting of the American Chemical Society, Orlando, FL, April 7-11, 2002, Division of Organic Chemistry, Abstract 350.

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1

Part of this work was presented at the 223^rd National Meeting of the American Chemical Society, Orlando, FL, April 7-11, 2002, Division of Organic Chemistry, Abstract 350.

12

Unpublished results from the authors’ laboratory.