Synthesis of benzobicyclo[2.2.1]heptylimidazoles as conformationally constrained adrenergic receptor antagonists

Jari Yli-Kauhaluoma; Aki Laine; Jari Ratilainen; Arto Karjalainen

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, Arto Karjalainen

VTT Technical Research Centre of Finland

Research output: Contribution to journal › Article › Scientific › peer-review

2 Citations (Scopus)

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.

Original language	English
Pages (from-to)	2783-2790
Journal	Heterocycles
Volume	65
Issue number	11
DOIs	https://doi.org/10.3987/COM-05-10535
Publication status	Published - 2005
MoE publication type	A1 Journal article-refereed

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title = "Synthesis of benzobicyclo[2.2.1]heptylimidazoles as conformationally constrained adrenergic receptor antagonists",

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{\textquoteright}s method.",

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AU - Laine, Aki

AU - Ratilainen, Jari

AU - Karjalainen, Arto

PY - 2005

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AB - 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.

U2 - 10.3987/COM-05-10535

DO - 10.3987/COM-05-10535

M3 - Article

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SP - 2783

EP - 2790

JO - Heterocycles

JF - Heterocycles

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