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Syntheses of 10‐Oxo‐10 H ‐pyrido[1,2‐ a ]thieno[3,4‐ d ]pyrimidines and 10‐Oxo‐10 H ‐pyrido[1,2‐ a ]thieno[3,2‐ d ]pyrimidines from methyl tetrahydro‐4‐oxo‐3‐thiophenecarboxylate and methyl tetrahydro‐3‐oxo‐2‐thiophenecarboxylate, respectively
Author(s) -
Connor David T.,
Sorenson Roderick J.,
Tinney Francis J.,
Cetenko Wiaczeslaw A.,
Kerbleski Joseph J.
Publication year - 1982
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.5570190539
Subject(s) - chemistry , pyrimidine , stereochemistry , carboxylic acid , d 1 , medicinal chemistry , organic chemistry , biochemistry , receptor
A general synthesis of 10‐Oxo‐10 H ‐pyrido[1,2‐ a ]thieno[3,4‐ d ]pyrimidines and 10‐Oxo‐10 H ‐pyrido[1,2‐ a ]‐thieno[3,2‐ d ]pyrimidines is described. Methyl tetrahydro‐4‐oxo‐3‐thiophenecarboxylate ( 13 ) was condensed with 6‐aminonicotinic acid ( 18 ) to give 3,10‐dihydro‐10‐oxo‐1 H ‐pyrido[1,2‐ a ]thieno[3,4‐ d ]pyrimidine‐7‐carboxylic acid ( 19 ). Treatment of 19 successively with chlorotrimethylsilane, N ‐chlorosuccinimide and water gave 10‐oxo‐10 H ‐pyrido[1,2‐ a ]thieno[3,4‐ d ]pyrimidine‐7‐carboxylic acid ( 17 ). Methyl tetrahydro‐3‐oxo‐2‐thiophenecarboxylate ( 21 ) was converted to 10‐oxo‐10 H ‐pyrido[1,2‐ a ]thieno[3,2‐ d ]pyrimidine‐7‐carboxylic acid ( 25 ) by an analogous route.