4-Fluoro-および4-Aminoquinazoline誘導体の合成ならびにC_4位フロンティア電子密度と反応性との関係 : N-ヘテロ芳香族の電子的性状第20報

概要

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4-Fluoro-6-nitroquinazoline (IIa), 4-fluoro-7-nitroquinazoline (IIb), 4-fluoro-8-nitroquinazoline (IIc), 5-chloro-4-fluoroquinazoline (IId), 6-chloro-4-fluoroquinazoline (IIe), 7-chloro-4-fluoroquinazoline (IIf), 8-chloro-4-fluoroquinazoline (IIg), and 6,8-dichloro-4-fluoroquinazoline (IIh) were prepared from the corresponding 4-chloroquinazoline derivatives (Ia-h) through fluorination with potassium fluoride in diethylene glycol, and the 4-fluoroquinazoline derivatives (IIa-h) were further treated with alcoholic ammonia to yeild 4-aminoquinazoline derivatives (IIIa-h). Effect of the substituents in the benzene ring on the reactivity in fluorination and amination, as well as in acid hydrolysis of the amino compounds, was examined and a roughly correspondent relationship was found to exist between the yield of the reaction products and frontier-electron density (f_r^<(N)>) at C_4 of the starting materials.
公益社団法人日本薬学会の論文
1968-04-25