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Review | Regular issue | Vol 81, No. 5, 2010, pp.1093-1140
Published online, 23rd February, 2010
DOI: 10.3987/REV-09-665
Recent Progress of New Catalytic Synthetic Methods for Nitrogen Heterocycles Based on Hydrogen Transfer Reactions

Ryohei Yamaguchi,* Ken-ichi Fujita, and Mingwen Zhu

*Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan

Abstract

This review summarizes a variety of synthetic methods for nitrogen heterocycles based on hydrogen transfer reactions catalyzed by transition metals in a past decade. Most of them employ iridium and ruthenium complexes as the catalysts and provide a versatile and environmentally benign synthetic methodology of various nitrogen heterocyclic compounds. Intermolecular cyclization reactions of amines with alcohols afford 5-7 membered alicyclic amines, quinolines, piperazines, indoles, quinoxalines, pyrroles, benzimidazoles, and benzoxazoles. Intramolecular cyclization reactions of amino alcohols give indoles, 1,2,3,4-tetrahydroqunolines, 1,2,3,4-tetrahydroquinoxalines, 3,4-dihydro-2(1H)-quinolinones, and oxindoles. Friedländer-type cyclization reactions provide a convenient route to various quinolines. Finally, cyclization reactions of amines with amines afford quinolines and phenylpyrrolidines.