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

An efficient palladium-catalyzed reaction of N-propargyl oxazolidines for the construction of 4-substituted isoquinolines under microwave irradiation is developed. This transformation proceeds through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade via C-O and C-N bond cleavages of the oxazolidine ring. The practical value of this method has also been explored by conducting a millimole-scale reaction, as well as by transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue. ©

Authors
Xu X. 1 , Feng H.2 , Van Der Eycken E.V.
Journal
Organic Letters
Number of issue
16
Language
English
Pages
6578-6582
Status
Published
Link
External link
DOI
10.1021/acs.orglett.1c02416
Volume
23
Year
2021
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Ku Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, 201620, China
  • 3 Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
Date of creation
16.12.2021
Date of change
16.12.2021
Short link
https://repository.rudn.ru/en/records/article/record/76697/
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