Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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


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.