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Synthesis of 6‐amino‐2‐aryl‐1,2‐dihydro‐3 H ‐pyrido[2,3‐ d ]pyrimidin‐4‐one derivatives
Author(s) -
Monge A.,
MartinezMerino V.,
Simon M. A.,
Sanmartin C.
Publication year - 1992
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.5570290629
Subject(s) - chemistry , aryl , stereochemistry , d 1 , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl , biochemistry , receptor
This paper reports the synthesis of new pyrido[2,3‐ d ]pyrimidin‐4‐one derivatives as diuretic agents. Starting with 1,2‐dihydro‐5‐nitro‐2‐oxo‐3‐pyridinecarboxylic acid 1 , ethyl 2‐ethoxy‐5‐nitro‐3‐pyridincarboxylate 4 was obtained. Compound 4 reacts with ammonia, methylamine or S ‐methylpseudothiourea to give the respective 2‐amino‐5‐nitro‐3‐pyridinecarboxamide derivatives 5 and 6 or 2‐methylthio‐6‐nitro‐3 H ‐pyrido[2,3‐ d ]pyrimidin‐4‐one 8. Treating carboxamide 5 with arylaldehydes and zinc dichloride, new 2‐aryl‐1,2‐dihydro‐6‐nitro‐3 H ‐pyrido[2,3‐ d ]pyrimidin‐4‐ones 9 were synthetised. These compounds reduced with iron(II) hydroxide gave 6‐amino‐2‐aryl‐1,2‐dihydro‐3 H ‐pyrido[2,3‐ d ]pyrimidin‐4‐ones 10 as expected.