Rh-catalyzed [3 + 2] cyclization of (hetero)cyclic 1,3-dicarbonyls with 2-aminoarylboronic esters to access carbazolones

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-09-24 DOI:10.1039/d5qo01079a

Bei Wan, Ce Liu, Haoyuan Xiong, Yi Deng, Zhonghua Gu, Shaoyu Mai, Feng Qiu, Qingfeng Du

引用次数: 0

Abstract

We report herein the first Suzuki-type [3 + 2] cyclization of cyclic 1,3-dicarbonyls with readily available 2-aminoarylboronic esters to synthesize carbazolones. With environmentally benign EtOH/H2O as solvent, a series of structurally and electronically diverse carbazolones can be readily obtained in a modular manner. This approach is mild, operationally simple, high-yield, scalable, and highly tolerant to moisture and air. Notably, it also exhibits excellent compatibility with various heterocyclic 1,3-dicarbonyls. The utility of this method has further been demonstrated by the late-stage functionalization of complex structures (e.g. styrylpyrone, simvastatin) and formal total synthesis of isocryptolepine.

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铑催化[3 + 2]杂环1,3-二羰基与2-氨基羰基硼酯的环化反应得到咔唑酮

本文首次报道了环1,3-二羰基与容易获得的2-氨基羰基硼酯的铃木型[3 + 2]环化合成咔唑酮。以环境友好的乙氧乙酸/水为溶剂，可以很容易地以模块化的方式得到一系列结构和电子结构多样的咔唑酮类化合物。这种方法温和，操作简单，产量高，可扩展，对水分和空气的耐受性高。值得注意的是，它还与各种杂环1,3-二羰基具有良好的相容性。复杂结构的后期功能化（如苯丙酮、辛伐他汀）和异ryptolepine的正式全合成进一步证明了该方法的实用性。

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.