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A facile synthesis of novel thiazolo[4,5‐d]pyrimidin‐7‐ones
Author(s) -
Liang Ying,
He HongWu,
Yang ZiWen
Publication year - 2011
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.515
Subject(s) - chemistry , carbodiimide , isocyanate , wittig reaction , triphenylphosphine , catalysis , medicinal chemistry , tandem , polymer chemistry , combinatorial chemistry , organic chemistry , polyurethane , materials science , composite material
Sixteen 5‐alkylamino‐3,6‐diaryl‐2‐thioxo‐2,3,6,7‐tetrahydrothiazolo[4,5‐d]pyrimidin‐7‐ones 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j , 4k , 4l , 4m , 4n , 4o , 4p were designed and easily synthesized via a tandem aza‐Wittig reaction. The iminophosphorane 2 , obtained from reaction of 1 with triphenylphosphine, hexachloroethane and Et 3 N, reacted with aromatic isocyanate to give carbodiimide 3 . carbodiimide 3 reacted with alkylamines to provide the title compounds in 45–61% isolated yields in presence of catalytic amount of ethoxide. The structures of compounds 4 were confirmed by 1 H NMR, IR, MS, and elemental analysis. J. Heterocyclic Chem., 2011.