Lewis Acids Catalyzed Regiodivergent N-alkylation of Indazoles with Donor-Acceptor Cyclopropanes

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-19 DOI:10.1039/d4qo01493f

Xiaoyan Zhang, Yujiao Xiang, Xiangyang Zhao, Xin Zhou, Weiliang Chen, Yungui Peng

引用次数: 0

Abstract

N-alkyl Indazoles are highly privileged skeleton in pharmaceutical applications. Generally, N1 and N2-alkyl indazoles represents distinct pharmaceutical and biological activities due to their molecular shape and electrostatic distribution. Herein, we described a regiodivergent N-alkylation of indazoles via nucleophilic ring opening of D-A cyclopropanes by employing different Lewis acid catalysts. Under the catalysis of Al(OTf)3, kinetic controlled N2-alkyl indazoles were achieved, while Co(NTf2)2 facilitated the formation of N1-alkyl indazoles. The methodology exhibited a broad substrate scope, affording the corresponding N1 and N2 alkylation products selectively in high yields with good to excellent regioselectivities.

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路易斯酸催化吲唑与供体-受体环丙烷的N-烷基化反应

N- 烷基吲唑在制药应用中是非常重要的骨架。一般来说，N1 和 N2-烷基吲唑因其分子形状和静电分布而具有不同的药物和生物活性。在此，我们介绍了利用不同的路易斯酸催化剂，通过 D-A 环丙烷的亲核开环，对吲唑进行变异性 N-烷基化反应。在 Al(OTf)3 的催化下，实现了 N2-烷基吲唑的动力学控制，而 Co(NTf2)2 则促进了 N1-烷基吲唑的形成。该方法具有广泛的底物范围，可选择性地高产率获得相应的 N1 和 N2 烷基化产物，并具有良好至卓越的区域选择性。

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.