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J Am Chem Soc. 2005 Jan 19;127(2):605-13.

Cp*RuCl-catalyzed [2 + 2 + 2] cycloadditions of alpha,omega-diynes with electron-deficient carbon-heteroatom multiple bonds leading to heterocycles.

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  • 1Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan.


In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes were allowed to react chemo- and regioselectively with electron-deficient nitriles and heterocumulenes at 60-90 degrees C to afford heterocyclic compounds. The mechanism of the ruthenium-catalyzed regioselective formations of bicyclic pyridines and pyridones were analyzed on the basis of density functional calculations. Cyclocotrimerizations of ethyl propiolate with ethyl cyanoformate or propyl isocyanate gave rise to two of the four possible pyridine or pyridone regioisomers.

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