Assembly of Isoquinolines via CuI-Catalyzed Coupling of β-Keto Esters and 2-Halobenzylamines

Bao Wang, Biao Lu, Yongwen Jiang, Yihua Zhang and Dawei Ma*

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: madwmail.sioc.ac.cn

B. Wang, B. Lu, Y. Jiang, Y. Zhang, D. Ma, Org. Lett., 2008, 10, 2761-2763.

DOI: 10.1021/ol800900a

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Abstract

CuI-catalyzed coupling of 2-halobenzylamines with β-keto esters or 1,3-diketones in i-PrOH in the presence of of K₂CO₃ produced 1,2-dihydroisoquinolines as the cyclization products, which underwent smooth dehydrogenation under air atmosphere to afford substituted isoquinolines.

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Key Words

Isoquinolines, Oxygen

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ID: J54-Y2008-1820