Next Article in Journal
Theoretical Studies on the Tautomerism of 1,5,6,7-Tetrahydro-4H-indazol-4-ones
Previous Article in Journal
Synthesis and Analgesic Activity Evaluation of Some Agmatine Derivatives
Article Menu

Export Article

Open AccessArticle
Molecules 2006, 11(6), 403-414; doi:10.3390/11060403

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
View Full-Text   |   Download PDF [87 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: Homophthalic anhydride; imine; tetrahydroisoquinolinones; stereochemistry. Homophthalic anhydride; imine; tetrahydroisoquinolinones; stereochemistry.

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top