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

IF 4.9 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

引用次数: 0

Abstract

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.