Asymmetric [3+2] Cycloannulation of Benzoxazinones for the Synthesis of Imidazo[5,1-c]oxazinones

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-24 DOI:10.1021/acs.orglett.5c00375

Tengfei Xuan, Xia Wang, Yang Wang

引用次数: 0

Abstract

The asymmetric catalytic [3+2] cycloannulation of benzoxazinones with isatin-derived ketimines for the efficient construction of imidazo[5,1-c]oxazinones has been developed, which realized the first asymmetric reaction of benzoxazinones with excellent stereoselectivities. A series of imidazo[5,1-c]oxazinones containing three stereogenic centers with one gem-diamine-type spiro tetrasubstituted center were obtained in this organocatalytic reaction with good yields and high functional group tolerance.

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苯并恶嗪酮不对称[3+2]环环合成咪唑[5,1-c]恶嗪酮

研究了苯并恶嗪酮与isatin衍生的酮类化合物之间的不对称催化[3+2]环环反应，以高效构建咪唑[5,1-c]恶嗪酮，实现了具有优异立体选择性的苯并恶嗪酮的首次不对称反应。在该有机催化反应中，得到了一系列咪唑[5,1-c]恶嗪酮类化合物，其中咪唑[5,1-c]恶嗪酮具有三个立体中心和一个双胺型螺旋四取代中心，产率高，官能团耐受性好。

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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.