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Synthesis of 5‐chloro‐2‐methyl‐3‐(5‐methylthiazol‐2‐yl)‐4(3 H )‐quinazolinone and related compounds with potential biological activity
Author(s) -
Párkányi Cyril,
Schmidt Duran S.
Publication year - 2000
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.5570370409
Subject(s) - chemistry , quinazolinone , substituent , ring (chemistry) , acetic anhydride , benzene , medicinal chemistry , mass spectrum , proton nmr , stereochemistry , organic chemistry , ion , catalysis
Eight new 2‐methyl‐4(3 H )‐quinazolinones (8a‐8d, 9c, 9d, 10c, 10d) with one or two chlorine atoms in the benzene ring and a 5‐methyl‐1,3‐thiazol‐2‐yl, 4‐methyl‐1,3‐thiazol‐2‐yl, and 5‐ethyl‐1,3,4‐thiadiazol‐2‐yl substituent in position 3 of the heterocyclic ring were synthesized and characterized. The two step procedure (Scheme 1) utilizes chlorosubstituted anthranilic acids (3a‐3d) and acetic anhydride as the starting materials, with the respective chlorosubstituted 2‐methyl‐4 H ‐3,1‐benzoxazin‐4‐ones (4a‐4d) as the intermediates. The quinazoline derivatives were characterized by their melting points, elemental analyses and the mass, ultraviolet, infrared, and 1 H and 13 C nmr spectra. The new compounds are expected to be biologically active.