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New trans/cis tetrahydroisoquinolines. 1. trans-2-benzyl-3-(l-methyl-1h-pyrrol-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolin-1-ones and corresponding tetrahydroisoquinolines

✍ Scribed by I. D. Kozekov; R. I. Koleva; M. D. Palamareva

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
82 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of homophthalic anhydride and N‐(1‐methyl‐1__H__‐pyrrol‐2‐yl‐methylidene)‐benzylamine in boiling benzene afforded as a main product the expected substituted trans‐1,2,3,4‐tetrahydroisoquinoline‐4‐carboxylic acid 5. The carboxylic group of 5 was transformed in four steps into cyclic amino‐methyl groups yielding numerous new tetrahydroisoquinolinones 11a‐j incorporating a given fragment of pharmacological interest. Reduction of 11a‐j was studied.

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## Abstract magnified image The parent compound 5‐oxo‐10a‐phenyl‐2,3,10,10a‐tetrahydro‐5__H__‐[1,3]‐oxazolo‐[3,2‐__b__]‐isoquinoline‐10‐carboxylic acid (**5**) was prepared in large scale and a good yield by reaction between homophthalic anhydride (**3**) and 4,5‐dihydro‐2‐phenyl‐1,3‐oxazole (**4*