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Regioselective synthesis of N (3) ‐ and O‐acylmethyl derivatives of 2‐methylthio‐4(3 H )‐quinazolinone
Author(s) -
Burbuliene Milda M.,
Mazeikaite Rita,
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.5570450250
Subject(s) - chemistry , regioselectivity , quinazolinone , dimethylformamide , potassium carbonate , sodium methoxide , acetonitrile , toluene , medicinal chemistry , methanol , ethyl bromoacetate , organic chemistry , alkylation , solvent , catalysis
Reaction of 2‐methylthio‐4(3 H )‐quinazolinone with chloroacetone, ω‐bromoacetophenone or ethyl bromoacetate in different solvents (methanol, acetonitrile, dimethylformamide and toluene) using sodium methoxide or potassium carbonate as a base were studied. Regioselective N (3) ‐alkylation took place in toluene using potassium carbonate, whereas in dimethylformamide O‐acylmethyl derivatives were obtained. However chloroacetone reacted with 2‐methylthio‐4(3 H )‐quinazolinone under various conditions to give a mixture of N (3) /O‐isomers.