Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones

Molecules

Meglena I. Kandinska¹  Ivan D. Kozekov² 

[1] Department of Chemistry, University of Sofia, 1 James Bouchier Avenue, Sofia 1164, Bulgaria;Vanderbilt University, Chemistry Department, P. O. Box 1822-B, Nashville, TN 37235, USA

关键词: Homophthalic anhydride;    imine;    tetrahydroisoquinolinones;    stereochemistry;   

DOI  :  10.3390/11060403

来源: mdpi

【 摘 要 】

The reaction of homophthalic anhydride and N-(furan-2-yl-methylidene)-benzylamine in different solvents and varying temperatures was studied in detail. Mixtures of the expected trans- and cis-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids trans-5 and cis-5, alongwith by-products 6 and 7 were obtained in dichloroethane or benzene. In pyridine, used for the first time, the reaction became completely diastereoselective, giving only the trans isomer. The carboxylic acid group of trans-5 was transformed in four steps into cyclic aminomethyl groups which yielded various new tetrahydroisoquinolinones trans-11a-g, incorporating both a known fragment of pharmacological interest and various pharmacophoric substituents.

【 授权许可】

Unknown   
© 2006 by MDPI (http:www.mdpi.org).