酮与六氟磷酸Vinamidinium环化:三取代吡啶的高效制备

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2000-06-30 DOI:10.1021/ol006097b

Jean-François Marcoux, Edward G. Corley, Kai Rossen, Phil Pye, Jimmy Wu, Michael A. Robbins, Ian W. Davies, Robert D. Larsen, Paul J. Reider

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引用次数: 35

摘要

α-芳基酮与六氟磷酸乙酰胺盐反应生成相应的3-芳基吡啶。在β-位(R2)含有吸电子基团的维酰胺盐中，环化反应的产率很高。该反应用于制备COX-2特异性抑制剂5-氯-3-(4-甲基磺酰基)苯基-2-(2-甲基-5-吡啶基)吡啶(1)及其一系列类似物。

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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Annulation of Ketones with Vinamidinium Hexafluorophosphate Salts: An Efficient Preparation of Trisubstituted Pyridines

α-Aryl ketones react with vinamidinium hexafluorophosphate salts to give access to the corresponding 3-arylpyridines. The annulation reactions proceed in good to excellent yields with vinamidinium salts containing electron-withdrawing groups at the β-position (R₂). The reaction was applied to the preparation of the COX-2 specific inhibitor 5-chloro-3-(4-methylsulfonyl)phenyl-2-(2-methyl-5-pyridinyl)pyridine (1), as well as a series of analogues.

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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.