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Synthesis and intramolecular cyclization of 2‐methylsulfany‐4‐oxo‐3(4 H )‐quinazolinyl)acetohydrazide
Author(s) -
Burbuliene Milda M.,
Bobrovas Olegas,
Vainilavicius Povilas
Publication year - 2006
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.5570430106
Subject(s) - chemistry , ethyl bromoacetate , medicinal chemistry , quinazolinone , hydrazine (antidepressant) , intramolecular force , hydrate , condensation , dimethylformamide , salt (chemistry) , alkyl , organic chemistry , physics , chromatography , solvent , thermodynamics
AbstractTreatment of ambident sodium salt of 2‐methylsulfanyl‐4(3 H )‐quinazolinone with methyl bromoacetate resulted in N (3) ‐alkyl ester formation. Reaction of the resulted ester with hydrazine hydrate gave 2‐methylsulfanyl‐4‐oxo‐3(4 H )‐quinazolinyl)acetohydrazide, which underwent intramolecular cyclization under heating in dimethylformamide to give 1‐aminoimidazo[2,1‐ b ]quinazoline‐2,5(1 H ,3 H )‐dione. The latter took place in acylation reaction and in condensation with aromatic aldehydes.