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 | Zendy

Connor David T. | Zendy; Sorenson Roderick J. | Zendy; Tinney Francis J. | Zendy; Cetenko Wiaczeslaw A. | Zendy; Kerbleski Joseph J. | Zendy

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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.

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