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Cyclization of 2‐benzoylamino‐ N ‐methyl‐thiobenzamides to 3‐methyl‐2‐phenylquinazolin‐4‐thiones
Author(s) -
Hanusek Jiří,
Drabina Pavel,
Sedlák MiloŠ,
Rosa Pavel
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.5570430521
Subject(s) - chemistry , sodium methoxide , acylation , medicinal chemistry , methoxide , sodium , sodium salt , ring (chemistry) , kinetics , nuclear magnetic resonance spectroscopy , catalysis , organic chemistry , inorganic chemistry , physics , quantum mechanics
Acylation of 2‐amino‐ N ‐methyl‐thiobenzamide with substituted benzoyl chlorides has been used to synthesize the corresponding 2‐benzoylamino‐ N ‐methylthiobenzamides. Subsequent sodium methoxide‐catalyzed ring closure gives the corresponding 3‐methyl‐2‐phenylquinazoline‐4‐thiones. These compounds were characterized by means of their 1 H‐ and 12 C‐NMR spectra. The kinetics of the cyclization reaction has been followed with UV‐VIS spectroscopy at 100 °C in methanolic solutions of sodium methoxide.