Synthesis of 2,3-Dihydro-4(1H)-pyrimidinones through Copper-Catalyzed Skeletal Rearrangement of Spirocyclic Aminimides

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI:10.1021/acs.orglett.6c03996

Motohiro Yasui, Seinosuke Okumura, Shion Fujitomo, Nozomi Ogasawara, Takahiro Yamada, Norihiko Takeda, Masafumi Ueda

引用次数: 0

Abstract

Aminimides are known to act as nitrene equivalents through N–N bond cleavage in Curtius-type rearrangements, but their use in other nitrene-type transformations is largely unexplored. Herein, we report a copper-catalyzed, atom-economical synthesis of 2,3-dihydro-4(1H)-pyrimidinones from alkynyl hydrazides. Control experiments suggest that the transformation proceeds via cyclization to form spirocyclic aminimides, followed by N–N bond cleavage and intramolecular C–H insertion.

查看原文本刊更多论文

铜催化螺旋环氨基胺骨架重排合成2,3-二氢-4(1h)-嘧啶

摘要：在curtius型重排中，氨基酰亚胺通过N-N键裂解作为亚硝基当量，但它们在其他亚硝基型转化中的应用在很大程度上尚未被探索。在此，我们报道了一种铜催化，原子经济的从炔酰肼合成2,3-二氢-4(1H)-嘧啶酮。对照实验表明，转化通过环化形成螺环胺酰，然后是N-N键断裂和分子内碳氢插入。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.