3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2025-03-27 DOI:10.1007/s11172-025-4540-7
E. S. Starnovskaya, A. L. Muzyka, A. A. Yurtaeva, A. E. Kopotilova, D. S. Kopchuk, V. S. Gaviko, O. S. Taniya, E. V. Nosova, G. V. Zyryanov, V. L. Rusinov
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Abstract

The cyclocondensation of 2-aminobenzamide with 3,4-dimethoxypyridine-2-carbaldehyde affords a mixture of 2-(3,4-dimethoxypyridin-2-yl)-2,3-dihydroquinazolin-4(1H)-one and its open-chain tautomer. The dehydrogenation of these compounds with benzoquinones (DDQ, chloranil) as oxidants, giving 2-(pyridin-2-yl)quinazolin-4(3H)-ones, is accompanied by the demethylation of the methoxy group at the C(3) position of the 2-pyridyl moiety. When using 2-methoxy- or 2,3,4-trimethoxybenzaldehydes as deaza analogs of this aldehyde, the demethylation does not occur in the last step regardless of the nature of the oxidant.

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3,4-二甲氧基吡啶-2-乙醛在喹唑啉-4(3H)-酮合成中的应用:脱氢步骤的部分去甲基化
2-氨基苯甲酰胺与3,4-二甲氧基吡啶-2-醛的环缩合反应得到2-(3,4-二甲氧基吡啶-2-基)-2,3-二氢喹唑啉-4(1H)- 1及其开链互变异构体的混合物。这些化合物以苯醌(DDQ,氯胺)为氧化剂脱氢,得到2-(吡啶-2-基)喹唑啉-4(3H)-酮,并伴有2-吡啶基部分C(3)位置的甲氧基的去甲基化。当使用2-甲氧基或2,3,4-三甲氧基苯甲醛作为该醛的脱氮类似物时,无论氧化剂的性质如何,在最后一步都不会发生去甲基化。
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来源期刊
Russian Chemical Bulletin
Russian Chemical Bulletin 化学-化学综合
CiteScore
2.70
自引率
47.10%
发文量
257
审稿时长
3-8 weeks
期刊介绍: Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.
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