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Facile Preparation of Various Heteroaromatic Compounds via Azatitanacyclopentadiene Intermediates

Daisuke Suzuki, Youhei Nobe, Yuko Watai, Ryoichi Tanaka, Yuuki Takayama, Fumie Sato* and Hirokazu Urabe

*Department of Biomolecular Engineering and Biological Information, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B-59 Nagatsuta-cho, Midori-ku, Yokohama, Kanagawa 226-8501, Japan, Email: fsatobio.titech.ac.jp

D. Suzuki, Y. Nobe, R. Tanaka, Y. Takayama, F. Sato, H. Urabe, J. Am. Chem. Soc., 2005, 127, 7474-7479.

DOI: 10.1021/ja0502730 (free Supporting Information)


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Abstract

Coupling of acetylene, nitrile, and a titanium reagent generated new azatitanacyclopentadienes in a highly regioselective manner. The subsequent reaction with sulfonylacetylene and electrophiles gave substituted pyridines virtually as a single isomer. Alternatively, the reaction of azatitanacyclopentadienes with an aldehyde or another nitrile gave furans or pyrroles having four different substituents again in a regioselective manner.

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Key Words

Pyridines, Furans, Pyrroles


ID: J48-Y2005-2370