4.5 Article

Facile Synthesis of 1-(Isoquinolin-1-yl)ureas by Silver Triflate Catalyzed Tandem Reactions of 2-Alkynylbenzaldoximes with Carbodiimides

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 33, Pages 6436-6439

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001040

Keywords

Alkynes; Fused-ring systems; Cycloaddition; Cyclization; Rearrangement; Silver

Funding

  1. National Natural Science Foundation of China [20972030]
  2. Science & Technology Commission of Shanghai Municipality [09JC1404902]

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2-Alkynylbenzaldoximes react with carbodiimides under mild conditions and silver triflate catalysis in DMF, leading to a diverse range of 1-(isoquinolin-1-yl)ureas in good to excellent yields. This transformation involves tandem 6-endo cyclization, [3+2] cycloaddition, and subsequent rearrangement.

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