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Synthesis 2010(3): 520-523  
DOI: 10.1055/s-0029-1217120
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Condensation-Oxidation of Glyoxamide with 1,2-Diamines Providing Imidazolines and Benzimidazoles

Kenichi Murai, Nobuhiro Takaichi, Yusuke Takahara, Shunsuke Fukushima, Hiromichi Fujioka*
Graduate School of Pharmaceutical Science, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565-0871, Japan
Fax: +81(66)8798229; e-Mail: fujioka@phs.osaka-u.ac.jp;
Further Information

Publication History

Received 7 September 2009
Publication Date:
13 November 2009 (online)

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Abstract

A novel method for the preparation of imidazolines and benzimidazoles bearing an amide at the 2-position, is described. The reactions of the glyoxamide with aliphatic and aromatic 1,2-diamines were found to form five-membered imidazolines and benzimidazoles by a one-pot condensation-oxidation procedure.

Key words

imidazolines - benzimidazolines - one-pot reaction - oxidations - amide

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Using two equivalents of NBS afforded complex mixtures.

15

Other reagents, such as NCS, NIS, NaClO2, oxone, TBHP, MCPBA, H2O2, CAN, and TsOH afforded poor results.