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Synthesis 2003(18): 2844-2850  
DOI: 10.1055/s-2003-42442
PAPER
© Georg Thieme Verlag Stuttgart · New York

Formation of Two 4-Imidazolylmethylphosphonium Salts and their Synthetic Studies Toward Histamine H3-Ligands

Shinya Harusawaa, Makoto Kawamuraa, Shuji Koyabua, Tomoko Hosokawaa, Lisa Arakia, Yasuhiko Sakamotob, Takeshi Hashimotoc, Yumiko Yamamotoc, Atsushi Yamatodanic, Takushi Kurihara*a
a Osaka University of Pharmaceutical Sciences, 4-20-1, Nasahara, Takatsuki, Osaka 569-1094, Japan
Fax: +81(72)6901086; e-Mail: kurihara@gly.oups.ac.jp;
b R&D Division, AZWELL, Inc., 2-24-3, Sho, Ibaraki, Osaka 567-0806, Japan
Fax: +81(72)6224999; e-Mail: ya-sakamoto@azwell.co.jp;
c Graduate School of Allied Health Sciences, Faculty of Medicine, Osaka University, Osaka 565-0871, Japan
Fax: +81(6)68792562; e-Mail: yamatoda@sahs.med.osaka-u.ac.jp;
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Publikationsverlauf

Received 25 August 2003
Publikationsdatum:
21. Oktober 2003 (online)

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Abstract

A simple and convenient preparation of {[1H-imidazol-4(5)-yl]methyl}triphenylphosphonium chloride (5) is described. The phosphonium salt 5 could be applied to the synthesis of 1-[1H-imidazol-4(5)-yl]-5-arylpentan- or 6-arylhexan-3-ones 4a-d exhibiting histamine H3-antagonistic activities via a 1,3-diazafulvene intermediate 6 generated from 5. Further, two-methylene-enlongated homolog 3 of imifuramine was efficiently synthesized, starting from Wittig olefination of aldehyde 24 using [(1-tritylimidazol-4-yl)methyl]triphenylphosphonium chloride 7.

Key words

imidazole - histamine H3-ligand - phosphonium salts - diazafulvene - Wittig olefination

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Dess-Martin periodinane was purchased from Lancaster or Aldrich.