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Synthesis of new 5-hydroxyquinazoline derivatives from functionalized 5-acetyl-6-methylpyrimidines
Chemistry of Heterocyclic Compounds ( IF 1.5 ) Pub Date : 2021-09-08 , DOI: 10.1007/s10593-021-02981-9
Alexander V. Komkov 1 , Mikhail A. Kozlov 1 , Yurii A. Linitskii 1, 2 , Leonid S. Vasil’ev 1 , Andrey S. Dmitrenok 1 , Igor V. Zavarzin 1
Affiliation  

A new method for the synthesis of quinazolines based on the annulation of the benzene ring to 5-acetyl-6 methylpyrimidin-2-one(thione) derivatives has been proposed. Condensation of the latter at the methyl group with dimethylformamide dimethyl acetal in boiling PhH leads to the formation of 5-acetyl-6-[2-(dimethylamino)vinyl]pyrimidin-2-ones(thiones), which, when boiled with MeONa in MeOH, cyclize to 5-hydroxyquinazolin-2-ones(thiones). Similarly, 5-acetyl-6-methyl-4-(trifluoromethyl)pyrimidine was converted to 5-hydroxy-4-(trifluoromethyl)quinazoline. Quinazolines are not formed from 5-acetyl-6-methylpyrimidines condensed with dimethylformamide dimethyl acetal at the acetyl group, but 5-acetyl-6-methylpyrimidines can be used to obtain pyrido[2,3-d] pyrimidine derivatives.



中文翻译:

从功能化的 5-乙酰基-6-甲基嘧啶合成新的 5-羟基喹唑啉衍生物

提出了一种基于苯环环化为 5-乙酰基-6 甲基嘧啶-2-酮(硫酮)衍生物合成喹唑啉的新方法。后者在沸腾的 PhH 中与二甲基甲酰胺二甲基缩醛在甲基上的缩合导致形成 5-乙酰基-6-[2-(二甲氨基)乙烯基]嘧啶-2-酮(硫酮),当与 MeONa 一起煮沸时, MeOH,环化为 5-羟基喹唑啉-2-酮(硫酮)。类似地,5-乙酰基-6-甲基-4-(三氟甲基)嘧啶转化为5-羟基-4-(三氟甲基)喹唑啉。喹唑啉不是由 5-乙酰基-6-甲基嘧啶与二甲基甲酰胺二甲基缩醛在乙酰基上缩合而成,但 5-乙酰基-6-甲基嘧啶可用于获得吡啶并[2,3- d ]嘧啶衍生物。

更新日期:2021-09-09
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