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Note | Regular issue | Vol 65, No. 11, 2005, pp.2783-2790
Published online, 6th September, 2005
DOI: 10.3987/COM-05-10535
Synthesis of Benzobicyclo[2.2.1]heptylimidazoles as Conformationally Constrained Adrenergic Receptor Antagonists

Jari Yli-Kauhaluoma,* Aki Laine, Jari Ratilainen, and Arto Karjalainen

*Technical Research Centre of Finland, VTT Processes, P.O. Box 1602, FI-02044 VTT, Finland

Abstract

A facile method for the preparation of conformationally rigid analogues of the adrenergic α-2 receptor antagonist atipamezole and the adrenergic α-2 receptor agonist medetomidine has been developed. The efficient benzyne [4+2] cycloaddition reaction was used to give the core 7-acetylbenzonorbornadiene structure, which was subsequently elaborated to the corresponding imidazole-based syn and anti isomers by means of the classical Bredereck’s method.