Intramolecular cycloadditions of N-alkenoyl aryl azides

Abstract

Depending upon the reaction conditions, intramolecular cycloadditions of variously substituted N-alkenoyl aryl azides 4 give the [1,2,3]triazolobenzodiazepine 5, bridgehead aziridines 6 or imines 7. The dipolarophilic activity of the C᎐ ᎐ N double bond of the latter compounds is also exploited in the synthesis of [1,2,4]triazolobenzodiazepines 10 by means of nitrilimine cycloadditions.