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New trans/cis tetrahydroisoquinolines. 2. trans‐ and cis ‐3‐(1‐methyl‐1h‐pyrrol‐2‐ y l)‐1‐(2 H )‐oxo‐2‐phenethyl‐1,2,3,4‐tetrahydroisoquino‐lin‐4‐carboxylic acids and subsequent transformations
Author(s) -
Stoyanova M. P.,
Kozekov I. D.,
Palamareva M. D.
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400508
Subject(s) - chemistry , diastereomer , phenethylamine , cis–trans isomerism , stereochemistry , solvent , medicinal chemistry , organic chemistry
Abstract Stereochemical course of the reaction of homophthalic anhydride and N ‐(1‐methyl‐1 H ‐pyrrol‐2‐yl‐methylidene)‐phenethylamine was studied. Mixtures of the expected trans ‐ and cis ‐1,2,3,4‐tetrahydroiso‐quinoline‐4‐carboxylic acids trans‐ 4 and cis‐ 4 were obtained along with by‐products 5 and 6 . The ratios of all products and the diastereomers, obtained under different reaction conditions, were established by pmr. THF as a solvent and ultrasonic treatment are applied for the first time in the reaction of this type. The reaction was made diastereoselective towards any isomer. The carboxylic group of trans‐ 4 was transformed in four steps into various cyclic amino‐methyl groups yielding numerous new tetrahydroisoquinolinones trans‐ 10a‐i incorporating a given fragment of pharmacological interest. Reduction of 10a‐i was studied.