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The synthesis of 8-hydroxyquinazoline derivatives and their acid-base interactions

✍ Scribed by Agnieszka Kudelko; Wojciech Zieliński

Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
179 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

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