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喹啉-N-氧化物的脱氧C2-杂芳基化反应:便捷合成α-三唑基喹啉

Deoxygenative C2-heteroarylation of quinoline -oxides: facile access to α-triazolylquinolines.

作者信息

Sontakke Geetanjali S, Shukla Rahul K, Volla Chandra M R

机构信息

Department of Chemistry, Indian Institute of Technology Bombay, Powai-400076, Mumbai, India.

出版信息

Beilstein J Org Chem. 2021 Feb 17;17:485-493. doi: 10.3762/bjoc.17.42. eCollection 2021.

Abstract

A metal- and additive-free, highly efficient, step-economical deoxygenative C2-heteroarylation of quinolines and isoquinolines was achieved from readily available -oxides and -sulfonyl-1,2,3-triazoles. A variety of α-triazolylquinoline derivatives were synthesized with good regioselectivity and in excellent yields under mild reaction conditions. Further, a gram-scale and one-pot synthesis illustrated the efficacy and simplicity of the developed protocol. The current transformation was also found to be compatible for the late-stage modification of natural products.

摘要

通过易于获得的α-氧化物和α-磺酰基-1,2,3-三唑,实现了喹啉和异喹啉的无金属、无添加剂、高效、步骤经济的脱氧C2-杂芳基化反应。在温和的反应条件下,以良好的区域选择性和优异的产率合成了多种α-三唑基喹啉衍生物。此外,克级规模的一锅法合成证明了所开发方法的有效性和简便性。还发现当前的转化反应适用于天然产物的后期修饰。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/35bd/7934756/5d11c399d963/Beilstein_J_Org_Chem-17-485-g002.jpg

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