SYNTHESIS OF 1-AZABICYCLO[3.3.1]NONADIENES BY INTRAMOLECULAR CYCLIZATION OF 1-(3-OXO-2-PHENYLBUTYL)TETRAHYDROPYRIDINES

Intramolecular cyclization reactions were performed with 1-(3-oxo-2-ph enylbutyl)-1,2,5,6-tetrahydropyridine derivatives 6a-h in sulfuric aci d to give 3,6-diphenyl-substituted 1-azabicyclo[3.3.1]nonadienes 9, Th e intermediate carbinols 7a-f and 8b, c could be isolated. Carrying ou t the reaction in methanesulfonic acid stereoselectivity was found in the formation of carbinols with preferential production of derivatives 7. Some of the compounds 9 show remarkable dopamine uptake inhibition .