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Synthesis of 2‐imino‐7‐methyl‐2,3‐dihydroimidazo[1,2‐ a ]‐pyrimidin‐5(1 H )‐ones and their reactions with nucleophiles
Author(s) -
Jakubkiene Virginija,
Kacnova Zana,
Burbuliene Milda M.,
Vainilavicius Povilas
Publication year - 2008
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.5570450522
Subject(s) - chemistry , acetonitriles , sodium methoxide , tautomer , benzylamine , methanol , medicinal chemistry , nucleophile , pyrimidine , ammonium chloride , ammonium , hydrolysis , base (topology) , catalysis , stereochemistry , organic chemistry , acetonitrile , mathematical analysis , mathematics
[2‐Alkylthio‐6‐methyl‐4‐oxopyrimidin‐3(4 H )‐yl]acetonitriles ( 3‐5 ) treated with sodium methoxide in methanol followed by ammonium chloride were cyclized to 2‐imino‐7‐methyl‐2,3‐dihydroimidazo[1,2‐ a ]‐pyrimidin‐5(1 H )‐ones ( 6‐8 ). Under acid or base‐catalyzed hydrolysis they were converted to 7‐methyl‐imidazo[1,2‐ a ]pyrimidine‐2,5‐[1 H ,3 H ]‐diones ( 9‐11 ), whereas in the reaction with butyl‐ or benzylamine the corresponding 7‐methyl‐2‐(substitutedamino)imidazo[1,2‐ a ]pyrimidin‐5(3 H )‐ones ( 13‐18 ) were produced. The latter were found to exist in two tautomeric forms in CDCl 3 solution.