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

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

{"title":"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","authors":"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","doi":"10.1007/s11172-025-4540-7","DOIUrl":null,"url":null,"abstract":"<div><p>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(1<i>H</i>)-one and its open-chain tautomer. The dehydrogenation of these compounds with benzoquinones (DDQ, chloranil) as oxidants, giving 2-(pyridin-2-yl)quinazolin-4(3<i>H</i>)-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.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"74 2","pages":"483 - 488"},"PeriodicalIF":1.7000,"publicationDate":"2025-03-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"3,4-Dimethoxypyridine-2-carbaldehyde in the synthesis of quinazolin-4(3H)-ones: partial demethylation at the dehydrogenation step\",\"authors\":\"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\",\"doi\":\"10.1007/s11172-025-4540-7\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>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(1<i>H</i>)-one and its open-chain tautomer. The dehydrogenation of these compounds with benzoquinones (DDQ, chloranil) as oxidants, giving 2-(pyridin-2-yl)quinazolin-4(3<i>H</i>)-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.</p></div>\",\"PeriodicalId\":756,\"journal\":{\"name\":\"Russian Chemical Bulletin\",\"volume\":\"74 2\",\"pages\":\"483 - 488\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2025-03-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Russian Chemical Bulletin\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11172-025-4540-7\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Chemical Bulletin","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11172-025-4540-7","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

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。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

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

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.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

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.