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Zirconocene-Mediated Cyclization of Bis(alkynyl)silanes and Nitriles: Synthesis of N-Heterocycles and Isolation, Characterization, and Synthetic Application of Zr/Si-Containing Reactive Intermediates

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The Chemistry of Zirconacycles and 2,6-Diazasemibullvalenes

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Abstract

Zirconocene-mediated one-pot multi-component synthesis of 5-azaindole derivatives from bis(alkynyl)silane and three molecules of nitriles were developed. Isolation and characterization of Zr/Si-containing three-ring-fused organometallic complexes were achieved as three or two nitriles involved reactive intermediates. Based on the reaction chemistry of reactive intermediates with unsaturated compounds, various N-heterocycles were synthesized, including 5-azaindoles, 3-acylpyrrole, dihydropyrrolo[3,2-c]azepines, pyrrolo[3,2-d]pyridazine, and pyrrolo[2,3-c]pyridinone derivatives.

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  1. College of Chemistry and Molecular Engineering, Peking University, Beijing, China

    Shaoguang Zhang

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Zhang, S. (2015). Zirconocene-Mediated Cyclization of Bis(alkynyl)silanes and Nitriles: Synthesis of N-Heterocycles and Isolation, Characterization, and Synthetic Application of Zr/Si-Containing Reactive Intermediates. In: The Chemistry of Zirconacycles and 2,6-Diazasemibullvalenes. Springer Theses. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-45021-5_2

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