Synthesis of 2-Hydroxymethyl-1H-imidazoles from 1,3-Dihydroimidazole-2-thiones

Yasser M. Loksha; Ahmed A. El-Barbary; Mahmoud A. El-Badawi; Claus Nielsen; Erik B. Pedersen

doi:10.1055/s-2003-44370

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Synthesis 2004(1): 116-120
DOI: 10.1055/s-2003-44370

PAPER

Synthesis of 2-Hydroxymethyl-1H-imidazoles from 1,3-Dihydroimidazole-2-thiones

Yasser M. Loksha^a, Ahmed A. El-Barbary^b, Mahmoud A. El-Badawi^b, Claus Nielsen^c, Erik B. Pedersen*^a
^a Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Campusvej 55, 5230 Odense M, Denmark
Fax: +4566158780; e-Mail: ebp@chem.sdu.dk;
^b Department of Chemistry, Faculty of Science, Tanta University, Tanta, Egypt
^c Retrovirus Laboratory, Department of Virology, State Serum Institute, Artillerivej 5, 2300 Copenhagen, Denmark

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Publication History

Received 12 September 2003
Publication Date:
09 December 2003 (online)

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Abstract

1,3-Dihydroimidazole-2-thiones 1a-d were desulfurized by hydrogen peroxide in either acid or neutral medium to afford 1H-imidazoles 3a-d. Reaction of 3b,d with dimethylsulfamoyl chloride furnished N,N-dimethylsulfamoylimidazoles 5 and 6a,b. Lithiation of 5 and 6a,b followed by formylation and reduction yielded the 2-hydroxymethyl derivatives 7 and 8a,b. 4-Alkyl-5-cyclohexylmethyl-1H-imidazol-2-yl)methanols 9a,b were obtained by hydrolysis of 7 and 8a,b.

Key words

1,3-dihydroimidazole-2-thiones - desulfurization - imidazole-2-sulfinic acids - 2-hydroxymetylimidazoles

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