三嗪烷与胺的伴随（3 + 3）环/断裂：多取代二氢嘧啶的电合成

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-06 DOI:10.1021/acs.orglett.5c00418

Jhilik Dutta, Sayan Ghosh, Aaliya Hassan, Suman De Sarkar

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引用次数: 0

摘要

报道了1,3,5-三嗪烷与胺对多取代1,2-二氢嘧啶的电氧化正（3 + 3）环反应。这种不含金属的温和方案具有广泛的官能团耐受性，并且具有未开发的分子支架的杂环以极好的产量构建。从机理上讲，三嗪烷的电氧化和烯胺的亲核反应性导致伴随的环裂解过程，从而产生六元杂环产物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Concomitant (3 + 3) Annulation/Fragmentation of Triazinanes with Enamines: Electrosynthesis of Multisubstituted Dihydropyrimidines

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Concomitant (3 + 3) Annulation/Fragmentation of Triazinanes with Enamines: Electrosynthesis of Multisubstituted Dihydropyrimidines

An electro-oxidative formal (3 + 3) annulation of 1,3,5-triazinanes with enamines toward multisubstituted 1,2-dihydropyrimidines is reported. This metal-free mild protocol offers wide functional group tolerance, and heterocycles with an unexplored molecular scaffold were constructed in excellent yields. Mechanistically, the electro-oxidation of triazinane and nucleophilic reactivity of enamine result in a concomitant annulation–fragmentation process, leading to the six-membered heterocyclic product.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.