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

Article abstract of DOI:10.1246/bcsj.68.3169

The photoadditions of ammonia and alkylamines (RNH₂) to 5-hydroxy- and 5-alkoxy-5H-dibenzo[a,d]-cycloheptene derivatives (2) occured 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.