用三氟重氮乙烷和乙腈介导的喹啉n -氧化物的c2 -酰胺化：获得2-N-（三氟乙基）氨基喹啉

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-20 DOI:10.1021/acs.orglett.4c04127

Anamika Dhami, Sanoop P. Chandrasekharan, Kishor Mohanan

引用次数: 0

摘要

本文介绍了路易斯酸介导的喹啉类化合物的c2 -N-三氟乙基酰胺化反应，采用喹啉N-氧化物、三氟重氮乙烷和乙腈合成了一类新的N-（喹啉-2-基）-N-（三氟乙基）乙酰胺。该反应通过生成羰基/生成腈基/(3 + 2)环加成/重排级联反应，以高收率制备喹啉-2- n -（三氟乙基）乙酰胺衍生物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

BF3-Mediated C2-Amidation of Quinoline N-Oxides Employing Trifluorodiazoethane and Acetonitrile: Access to 2-N-(Trifluoroethyl)amidoquinolines

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BF3-Mediated C2-Amidation of Quinoline N-Oxides Employing Trifluorodiazoethane and Acetonitrile: Access to 2-N-(Trifluoroethyl)amidoquinolines

A Lewis acid-mediated C2-N-trifluoroethylamidation of quinolines, employing quinoline N-oxides, trifluorodiazoethane, and acetonitrile to forge a new class of N-(quinolin-2-yl)-N-(trifluoroethyl)acetamide is presented in this Letter. The reaction proceeds through a carbene generation/nitrile ylide formation/(3 + 2) cycloaddition/rearrangement cascade to furnish quinoline-2-N-(trifluoroethyl)acetamide derivatives in high yields.

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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.