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Synthesis of 5‐fluoro‐2‐methyl‐3‐(2‐trifluoromethyl‐1,3,4‐thiadiazol‐5‐yl)‐4(3 H )‐quinazolinone and related compounds with potential antiviral and anticancer activity
Author(s) -
Párkányi Cyril,
Yuan Hui Liang,
Strömberg Bo H. E.,
Evenzahav Ariella
Publication year - 1992
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.5570290411
Subject(s) - chemistry , quinazolinone , acetic anhydride , anthranilic acid , thiadiazoles , yield (engineering) , condensation , medicinal chemistry , acetic acid , trifluoromethyl , organic chemistry , catalysis , materials science , physics , metallurgy , thermodynamics , alkyl
The synthesis of ten new substituted 1,3,4‐thiadiazolyl‐4(3 H )‐quinazolinones 8–11, 13, 17 , and 20–23 is reported. Compounds 8–11 were prepared by condensation of 5‐fluoro‐2‐methyl‐3,1‐benzoxazin‐4‐one (3) and 5‐substituted 2‐amino‐1,3,4‐thiadiazoles 4–7. Compound 13 was obtained by condensation of 5‐fluoro‐2‐methyl‐3,1‐benzoxazin‐4‐one (3) with DL‐α‐amino‐ϵ‐caprolactam (12) . Compound 17 was synthesized by condensation of 6‐bromo‐2‐methyl‐3,1‐benzoxazin‐4‐one (16) and 2‐amino‐5‐ t ‐butyl‐1,3,4‐thiadiazole (5) . Compounds 20–23 were obtained by condensation of 5‐chloro‐6,8‐dibromo‐2‐methyl‐3,1‐benzoxazin‐4‐one (19) and 5‐substituted 2‐amino‐1,3,4‐thiadiazoles 4–7, respectively. The substituted 3,1‐benzoxazin‐4‐ones 3, 16, and 19 were obtained in good yield by refluxing the appropriate anthranilic acid, 1,15 , and 18 with acetic anhydride (2) .