Regioselective synthesis of N (3) ‐ and O‐acylmethyl derivatives of 2‐methylthio‐4(3 H )‐quinazolinone | Zendy

Burbuliene Milda M. | Zendy; Mazeikaite Rita | Zendy; Vainilavicius Povilas | Zendy

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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.

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