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Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones
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
* Author to whom correspondence should be addressed.
Received: 10 May 2006 / Accepted: 8 June 2006 / Published: 12 June 2006
Abstract: 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.
Keywords: Homophthalic anhydride; imine; tetrahydroisoquinolinones; stereochemistry.
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Kandinska, M.I.; Kozekov, I.D.; Palamareva, M.D. Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones. Molecules 2006, 11, 403-414.
Kandinska MI, Kozekov ID, Palamareva MD. Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones. Molecules. 2006; 11(6):403-414.
Kandinska, Meglena I.; Kozekov, Ivan D.; Palamareva, Mariana D. 2006. "Synthesis of New trans-2-Benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones." Molecules 11, no. 6: 403-414.