Syntheses of 10-Oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidines and 10-Oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidines from methyl tetrahydro-4-oxo-3-thiophenecarboxylate and methyl tetrahydro-3-oxo-2-thiophenecarboxylate, respectively

Autor: Joseph J. Kerbleski, Francis J. Tinney, Wiaczeslaw A. Cetenko, Roderick J. Sorenson, David T. Connor
Rok vydání: 1982
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 19:1185-1188
ISSN: 1943-5193
0022-152X
Popis: A general synthesis of 10-Oxo-10H-pyrido[1,2-a]thieno[3,4-d]pyrimidines and 10-Oxo-10H-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-1H-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-10H-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-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid (25) by an analogous route.
Databáze: OpenAIRE
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