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Synfacts 2010(2): 0150-0150  
DOI: 10.1055/s-0029-1219120
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

AgOTf/Bi(OTf)3-Catalyzed Synthesis of Isoquinolines

Contributor(s): Victor Snieckus, Alcides da Silva
Z. Chen, X. Yu, M. Su, X. Yang, J. Wu*
Fudan University, Shanghai and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
21 January 2010 (online)

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Significance

A useful method for the direct ­synthesis of 1-formamido isoquinolines from 2-alkynylbenzaldoximes catalyzed by AgOTf and Bi(OTf)3 is described. For this apparent multicatalytic tandem reaction, the optimized conditions use silver and bismuth triflate in 1,4-dioxane and lead to the isoquinolines in good to excellent yields. In terms of substrate scope, the presence of an aromatic system (Ph, 4-MeOC6H4) or alkyl group (c-Pr, n-Bu) as R² did not influence directly the yield of the products. However, only R¹ = H, F were tested. Aryl and alkyl isocyanides (R³) appear to be useful coupling substrates. A possible mechanism for this reaction was proposed.