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:

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

Paper | Regular issue | Vol 31, No. 7, 1990, pp.1359-1369
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5426
Synthesis of 4-Methyl-2-benzazepin-3-one Analogs of Diltiazem

John T. Hunt,* Mary F. Malley, and Jack Z. Gougoutas

*The Squibb Institute for Medical Research, P. O. Box 4000, Princeton, N.J. 08540-4000, U.S.A.


An efficient method for the preparation of an alternative benzazepinone ring fusion, the cis and trans isomers of 4-methyl-5-(4-methoxyphenyl)-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one (3), is described. The key reaction involved the ZnCl2-catalyzed alkylation of 3-(4-methoxyphenyl)phthalide (4) with the trimethylsilylketene acetal of ethyl propionate to form 5 as a mixture of diastereomers. Selective reductionof the carboxylic acid, conversion of the primary alcohol to the primary amine and cyclization produced the isomers of 3, which were separated by crystallization. The solid state conformation of the cis isomer (10) and a related 1-benzazepin-2-one were compared.