高价碘介导酮肟与烯烃氧化环化合成异喹啉n -氧化物

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-05 DOI:10.1021/acs.joc.5c0048810.1021/acs.joc.5c00488

Aurapat Ngamnithiporn*, Padon Chuentragool, Supakarn Punnita, Wachirawit Thitseesaeng, Teesuda Sirichai, Shinji Harada, Tetsuhiro Nemoto, Poonsakdi Ploypradith and Somsak Ruchirawat,

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引用次数: 0

摘要

本文报道了酮肟与烯烃分子内氧化环化制备异喹啉n -氧化物的进展。该反应以苯基吡啶二（三氟乙酸酯）（PIFA）为氧化剂，2,2,2-三氟乙醇（TFE）为溶剂，生成各种n -杂环产物，包括芳基/杂芳基融合吡啶n -氧化物、异吲哚n -氧化物和2-苯并平衍生物。初步的实验和计算机制研究表明，离子途径是主要的机制。通过几个乘积变换，突出了所开发方法的综合效用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Synthesis of Isoquinoline N-Oxides via Hypervalent Iodine-Mediated Oxidative Cyclization of Ketoximes with Alkenes

Reported herein is the development of an intramolecular oxidative cyclization of ketoximes with alkenes for the preparation of isoquinoline N-oxides. The reaction, which utilizes phenyliodine bis(trifluoroacetate) (PIFA) as an oxidant and 2,2,2-trifluoroethanol (TFE) as a solvent, proceeds to afford various N-heterocyclic products, including aryl/heteroaryl-fused pyridine N-oxides, isoindole N-oxides, and 2-benzazepine derivatives. Preliminary experimental and computational mechanistic studies suggest that the ionic pathway is the primary mechanism. The synthetic utility of the developed method was highlighted via several product transformations.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.