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Communication | Special issue | Vol 80, No. 2, 2010, pp.917-924
Published online, 14th October, 2009
DOI: 10.3987/COM-09-S(S)126
Synthesis of Substituted Isoquinolines via Nickel-Catalyzed [2+2+2] Cycloaddition of Alkynes and 3,4-Pyridynes

Toshihiko Iwayama and Yoshihiro Sato*

*Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita 12 Nishi 6, Kita-ku, Sapporo, Hokkaido 060-0812, Japan


A novel methodology for the synthesis of substituted isoquinolines via a nickel(0)-catalyzed [2+2+2] cycloaddition of 3,4-pyridynes with two molecules of alkyne has been established. In this reaction, it was found that 2-butyn-1,4-diol derivatives and 1,3-diynes are suitable as substrates and that a propargylic oxygen functionality in alkynes is essential for the reactivity and the selectivity of the products.