在Cu2O存在下，2-碘- n -甲酰基胺和炔酮序烷基化和环化一锅法合成2-取代吲哚和7-氮杂吲哚。

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-01-01 DOI:10.1002/ajoc.202400421

Ahmed R. Ali , Longqin Hu

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引用次数: 0

摘要

以2-碘- n -甲酰基胺和末端炔为起始原料，在Cu2O存在下，在90 ~ 120℃的DMF中，采用一锅法，以中高收率合成了一系列2-取代吲哚和7-氮唑。在不分离任何中间体的情况下，我们优化的条件可以在吲哚和7-氮杂吲哚的2位上引入酯、苯基、羟甲基、羟乙基、n - boc -氨基甲基和甲基。该反应耐受各种含卤素或酸或碱敏感官能团的底物，而不需要钯催化剂、配体或碱。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

One‐Pot Synthesis of 2‐Substituted Indoles and 7‐Azaindoles via Sequential Alkynylation and Cyclization of 2‐Iodo‐N‐mesylarylamines and Alkynes in the Presence of Cu2O

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One‐Pot Synthesis of 2‐Substituted Indoles and 7‐Azaindoles via Sequential Alkynylation and Cyclization of 2‐Iodo‐N‐mesylarylamines and Alkynes in the Presence of Cu2O

A one‐pot process was developed to synthesize in moderate to high yield a series of 2‐substituted indoles and 7‐azaindoles starting from 2‐iodo‐N‐mesylarylamines and terminal alkynes in the presence of Cu₂O in DMF at 90–120 °C. Without isolation of any intermediate, our optimized conditions enabled the introduction of ester, phenyl, hydroxymethyl, hydroxyethyl, N‐Boc‐aminomethyl, and methyl at the 2‐postion of indoles and 7‐azaindoles. The reaction tolerates a variety of substrates containing halogens, or acid‐ or base‐sensitive functional groups without requiring a Pd catalyst, a ligand, or a base.

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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.