New Synthetic Route to 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines through Photoamination of 5-Alkoxy- and 5-Hydroxy-5H-dibenzo[a,d]cycloheptenes Followed by a Transannular Reaction with Acetic Acid

Abstract

Abstract The photoadditions of ammonia and alkylamines (RNH2) to 5-hydroxy- and 5-alkoxy-5H-dibenzo[a,d]cycloheptene derivatives (2) occurred at the C10–C11 double bond upon the irradiation of 2 with RNH2 in the presence of p-dicyanobenzene. The resulting 5-substituted 10-alkylamino-10,11-dihydro-5H-dibenzo[a,d]cycloheptenes were converted to 5-substituted N-alkyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines by a treatment with AcOH.