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The synthesis of 8‐hydroxyquinazoline derivatives and their acid‐base interactions
Author(s) -
Kudelko Agnieszka,
Zieliński Wojciech
Publication year - 2004
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.5570410215
Subject(s) - chemistry , cyanamide , hydrolysis , titanium tetrachloride , catalysis , aqueous solution , cleavage (geology) , base (topology) , medicinal chemistry , ether , aqueous medium , organic chemistry , mathematical analysis , geotechnical engineering , mathematics , fracture (geology) , engineering
The reaction of N ‐(2‐R 1 ‐oxyphenyl)benzimidoyl chlorides with cyanamide derivatives in the presence of titanium tetrachloride as a catalyst has yielded some new 4‐amino‐8‐R 1 ‐oxy‐2‐phenylquinazolines. pK a values have been determined for these compounds and the influence of substituents at the basicity of the parent system has been discussed. Some investigations on the methyl‐quinazolinyl ether cleavage in different medium have been done yielding the appropriate hydroxyquinazoline derivatives. In those cases when the deprotection of 4‐amino‐8‐methoxy‐2‐phenylquinazoline was carried in aqueous acidic solutions, the formation of the hydrolysis products 3,4‐dihydro‐2‐phenyl‐4‐quinazolone derivatives was observed as well.