A concise route to novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexanes

A number of novel 1-aryl and 1-pyridyl-2-azabicyclo[2.1.1]hexane derivative s were prepared by an intramolecular [2+2] photocydoaddition in the presenc e of acetophenone as the sensitizer. Substitution of the azabicyclo[2.1.1]h exane ring was accomplished by appropriate choice of the heteroaryl ketone and allylamine starting materials. Several aryl 9a-e, g and pyridyl analogs 9h-l were prepared by this method. The structures of 9a and 9i were verifi ed by X-ray crystallography. Several of the photoproducts 9 were converted into the corresponding N-Me and N-H 2,4-methanonicotine analogs 4 by reduct ion or hydrolysis of the N-carboethoxy group.