Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines

Xianjun Xu, Huangdi Feng* and Erik V. Van der Eycken*

*Shanghai University of Engineering Science, Shanghai 201620, PR China; KU Leuven, Celestijnenlaan 200F, Leuven B-3001, Belgium, Email: hdfengsues.edu.cn, erik.vandereyckenkuleuven.be

X. Xu, H. Feng, E. V. Van der Eycken, Org. Lett., 2021, 23, 6578-6582.

DOI: 10.1021/acs.orglett.1c02416

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Abstract

An efficient palladium-catalyzed reaction of N-propargyl oxazolidines provides 4-substituted isoquinolines under microwave irradiation through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade via C-O and C-N bond cleavages of the oxazolidine ring.

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proposed mechanism

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Key Words

isoquinolines, microwave synthesis, formates

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ID: J54-Y2021