Water-enabled α-C(sp3)–H amination via [1,6]-hydride transfer: green access to diazepino[6,5,4-cd]indoles

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-21 DOI:10.1039/d4qo01761g

Yao-Bin Shen, Xiao-Lin Wang, Qian-Hao Zhuang, Xiao-De An, Bin Qiu, Houchen Wang, Tiesheng Shi, Jian Xiao

引用次数: 0

Abstract

Water is an ideal green reaction medium in organic synthesis, and the development of water-enabled transformations to synthesize high value-added molecules is particularly attractive but challenging. Herein, we disclosed the water-enabled α-C(sp³)–H amination of 4-dialkylamino-indole-3-carbaldehydes with primary amines for one-step green synthesis of diazepino[6,5,4-cd]indole derivatives. This reaction proceeded via a cascade aldimine condensation/[1,6]-hydride transfer/cyclization sequence, which featured redox-neutral conditions, water as the green reaction medium, simple operation, high atom- and step-economy, and excellent functional group tolerance.

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通过[1,6]酸酐转移实现水驱动的α-C(sp3)-H胺化：二氮杂卓[6,5,4-cd]吲哚的绿色获取途径

在有机合成中，水是一种理想的绿色反应介质，开发水引发的转化来合成高附加值分子尤其具有吸引力和挑战性。在此，我们公开了 4-二烷基氨基吲哚-3-羰基醛与伯胺的α-C(sp3)-H 水胺化反应，用于一步法绿色合成二氮杂卓[6,5,4-cd]吲哚衍生物。该反应通过级联醛亚胺缩合/[1,6]-酸酐转移/环化顺序进行，具有氧化还原中性条件、水作为绿色反应介质、操作简单、原子和步骤经济性高以及官能团耐受性优异等特点。

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

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.