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Synthesis of Isoquinolines and Heterocycle-Fused Pyridines via Three-Component Cascade Reaction of Aryl Ketones, Hydroxylamine, and Alkynes

Liyao Zheng, Jia Ju, Yunhui Bin and Ruimao Hua*

*Department of Chemistry, Tsinghua University, Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, China, Email: ruimaomail.tsinghua.edu.cn

L. Zheng, J. Ju, Y. Bin, R. Hua, J. Org. Chem., 2012, 77, 5794-5800.

DOI: 10.1021/jo3010414 (free Supporting Information)



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Abstract

An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by a three-component reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C-H bond activation of the in situ generated oxime, and cyclization with an internal alkyne. This protocol enables rapid assembly of multisubstituted isoquinolines as well as fused heterocycles.

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Key Words

Isoquinolines, Multicomponent Reactions


ID: J42-Y2012-2230