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Synthesis 2002(8): 1072-1078
DOI: 10.1055/s-2002-31951
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient and Convenient Synthesis of 4-Vinylimidazoles Using a Novel Horner-Wadsworth-Emmons (HWE) Reagent: Synthetic Studies Toward Novel Histamine H3-Ligands

Shinya Harusawaa, Shuji Koyabua, Yasutoshi Inouea, Yasuhiko Sakamotob, Lisa Arakia, Takushi Kurihara*a
a Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan
Fax: +81(726)901086; e-Mail: kurihara@gly.oups.ac.jp;
b R&D Division, AZWELL, Inc., 2-24-3, Sho, Ibaraki, Osaka 567-0806, Japan
Fax: +81(726)224999; e-Mail: nskrd-12@mbd.sphere.ne.jp;
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Publication History

Received 20 February 2002
Publication Date:
03 June 2002 (online)

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Abstract

A novel Horner-Wadsworth-Emmons (HWE)-type reagent 1 reacted readily with various aldehydes and ketones to produce (E)-vinylimidazoles 2 in good yields. The synthetic utility of 1 was demonstrated by the efficient preparation of four histamine H3 ligands 3 by simple hydrogenation of 2.

Key words

Horner-Wadsworth-Emmons reaction - vinylimidazole - hydrogenation - H3 ligands - immepip

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13

All yields are of the pure products after chromatography.