Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 26, No. 12, 1987, pp.3165-3172
Published online, 1st January, 1970
DOI: 10.3987/R-1987-12-3165
Synthesis of 1,2,3,4,4a,5,9,10,16,16a-Decahydro-2-methyl[1]benzazepino [3,2,1-jk]Pyrido[3,4-b][1]benzazepine: A Conformationally Rigid Imipramine Analog

Philip G. Dunber and Arnold R. Martin

*Department of Pharmaceutical Sciences, College of Pharmacy, The University of Arizona, Tucson, AZ 85721, U.S.A.

Abstract

Ortho lithiations and acylations of 10,11-dihydro-5H-dibenz[b,f]azepine and N,N-diethylnicotinamide respectively led to the convenient synthesis of the key intermediate 4-[(10,11-dihydro-5H-dibenz[b,f]azepin-4-yl)hydroxymethyl]-N,N-diethylnicotinamide 2a, Catalytic reduction of 2, and subsequent cyclization of the resulting carboxylic acid 3, provided the pentacyclic lactam 4 required for further elaboration of the rigid imipramine analog. Difficulties in amide hydrolysis are discussed. Further reductions and N-methylation provided both cis and trans ring fusion isomers 8a and 8b identified by 1H and 13C nmr.