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Saturated heterocycles, Part 172 . Synthesis of 2,6‐disubstituted‐5,6,7,8‐tetrahydropyrido[4,3‐ d ]pyrimidine derivatives
Author(s) -
Lázár János,
Bernáth Gábor
Publication year - 1990
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.5570270708
Subject(s) - chemistry , benzylamine , hydrogenolysis , yield (engineering) , pyrimidine , alkylation , medicinal chemistry , condensation , nitrogen atom , stereochemistry , organic chemistry , group (periodic table) , catalysis , materials science , physics , metallurgy , thermodynamics
The title compounds were synthesized via the addition of methyl acrylate to benzylamine or to α‐aminopyridine, which gave the corresponding diesters, e.g . 12 , followed by Dieckmann condensation of the latter to yield the keto‐esters 13 , which were condensed with amidines and guanidines, 3, 14 . Removal of the benzyl group by hydrogenolysis and subsequent alkylation of the nitrogen atom at position 6 in the resulting compound 5 , with variation of the substituents on C‐2, gave a number of products with potential biological action; some of them gave analgesic and anti‐inflammatory effects.