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Synfacts 2011(6): 0593-0593  
DOI: 10.1055/s-0030-1260453
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Synthesis of Isoquinolines from Oximines and Alkynes

Contributor(s): Victor Snieckus, Yigang Zhao
X. Zhang, D. Chen, M. Zhao, J. Zhao*, A. Jia*, X. Li*
Nanjing University, Dalian Institute of Chemical Physics and Nanjing University of Science and Technology, P. R. of China
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

A synthesis of multisubstituted isoquinolines is presented, which involves a rhodium-catalyzed directed C-H activation of oximes and subsequent formal [4+2] cycloaddition with alkynes. The reaction proceeds smoothly under mild conditions to afford diverse 1,3,4-trisubsti­tuted isoquinolines in moderate to good yields. When ketoximes are replaced by aldoximes, the reaction efficiency is greatly reduced. Unsymmetrical alkynes are applicable, but the products of these reactions are regioisomerically compromised to some extent, depending on the alkyne substrates. The reaction scope and limitations were not well investigated.