Green and modular synthesis of azepino[4,3,2-cd]indoles and diazepino[6,5,4-cd]indoles via hydride transfer-involved cascade cyclization in ethanol

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-04-22 DOI:10.1039/d5qo00058k

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

引用次数: 0

Abstract

The modular synthesis of high-value azepino[4,3,2-cd]indole and its analogs from versatile synthons and readily available feedstocks has been a challenging project. Herein, we report the 1,6-hydride transfer-involved cascade [6 + 1] cyclization of 4-dialkylamino-indole-3-carbaldehydes with diverse 1C,1C- and 1N,1N -bisnucleophiles in ethanol, enabling the green and modular synthesis of diazepino[6,5,4-cd]indoles and diazepino[6,5,4-cd]indoles. This method highlights catalyst-free redox-neutral conditions, excellent substrate compatibility, simple operational procedures, gram-scale synthesis, and diverse product derivatization.

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乙醇中氢化物转移级联环化绿色模块化合成氮平[4,3,2-cd]吲哚和二氮平[6,5,4-cd]吲哚

利用多种多样的合成物和现成的原料，模块化合成高价值的氮杂吲哚[4,3,2-cd]及其类似物一直是一个具有挑战性的项目。在本文中，我们报道了1,6-氢化物转移参与级联[6 + 1]环化4-二烷基氨基-吲哚-3-乙醛与不同的1C，1C-和1N，1N -双亲核试剂在乙醇中，实现了绿色和模块化合成二氮平[6,5,4-cd]吲哚和二氮平[6,5,4-cd]吲哚。该方法具有无催化剂氧化还原中性条件，良好的底物相容性，简单的操作程序，克级合成和多样化的产品衍生性。

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.