Conjugate Addition of 3‐Aryl Oxindoles to In Situ Generated o–Quinone Methides Without Essential Electronic or Steric Groups

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2024-12-01 DOI:10.1002/ajoc.202400370

Liu Song

引用次数: 0

Abstract

Herein an efficient method for in situ generated o–quinone methides without essential electronic or steric groups at the exocyclic methylene or on six‐membered ring was established. The method relies on acetylation of salicylylols and subsequently base promoted 1,4‐elimination. The in situ generated o–quinone methides could be undergoing conjugate addition with 3‐aryl oxindoles in one‐pot reaction system, which provided 3,3‐disubstituted oxindoles bearing a quaternary stereocenter in good yields (up to 99 %).

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3 芳基羰基吲哚与原位生成的邻喹酮甲酰胺的共轭加成，不含基本电子或立体基团

本文建立了一种原位生成邻醌的有效方法，该方法在外环亚甲基或六元环上没有必要的电子或空间基团。该方法依赖于水杨醇的乙酰化，随后碱促进1,4消除。原位生成的邻醌类化合物可与3-芳基氧吲哚在一锅反应体系中进行共轭加成，得到含季立体中心的3,3-二取代氧吲哚，收率可达99%。

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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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.