Intramolecular [2+2] Photocycloaddition of 2-[N-Acyl-N-(2-propenyl)-amino] cyclohex-2-enones : Synthesis of 2-Azabicyclo [2.1.1] hexanes

Abstract

Photoirradiation of 2-[N-acyl-N-(2-propenyl) amino] cyclohex-2-enones gave the 9-acyl-9-azatricyclo [5.2.1.0^1.6] decan-2-ones as the major products. In some cases, 1-acetyl-1, 4, 4a, 5, 6, 7, 8, 8a-octahydroquinol-8-one, 1-benzoyl-3-vinyl-2, 3, 3a, 4, 5, 6, 7, 7a-octahydroindol-7-one, and 1-(2-propenyl)-1-azaspiro [3.5] nonane-2, 5-dione were isolated and characterized as minor products.