协同[4 + 1]螺环化和选择性开环策略，用于γ-螺内酰胺

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-07 DOI:10.1021/acs.orglett.4c03669

Imtiaj Mondal, Koushik Naskar, Shantonu Roy, Anisha Purkait, Indubhusan Deb

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引用次数: 0

摘要

2- 芳基-4H-苯并[d][1,3]恶嗪与马来酰亚胺独特而有利的[4 + 1]螺环化反应已经得到描述、Rh(III)催化的连续闭环/开环，然后在原位生成的水机动作用下，1,3-苯并恶嗪的 C4-O 键发生区域选择性裂解，一次构建出新的 C-C、C-N 和 C-O 键，从而产生了具有悬垂苄醇的多种γ-螺内酰胺。详细的机理研究，包括对加入额外氧源的透彻分析，展示了这种用于结构协调的异吲哚啉-1-酮螺琥珀酰亚胺的策略。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synergistic [4 + 1] Spiroannulation and Selective Ring-Opening Strategy toward γ-Spirolactams

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Synergistic [4 + 1] Spiroannulation and Selective Ring-Opening Strategy toward γ-Spirolactams

A unique and propitious [4 + 1] spiroannulation of 2-aryl-4H-benzo[d][1,3]oxazine with maleimide has been delineated, furnishing diversely embellished γ-spirolactams featuring pendant benzyl alcohol via Rh(III)-catalyzed consecutive ring closing/ring opening followed by regioselective cleavage of the C4–O bond of 1,3-benzoxazine promoted by an in situ generated water maneuver constructing new C–C, C–N, and C–O bonds at a go. A detailed mechanistic study, including a thorough analysis of the incorporation of an extra oxygen source, has been showcased to make this strategy for structurally orchestrated isoindoline-1-one spirosuccinimides.

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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.