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

Access to Document

10.3987/COM-05-10535

Cite this

@article{b020b455fb3449b7be6a388ae6259164,

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.",

author = "Jari Yli-Kauhaluoma and Aki Laine and Jari Ratilainen and Arto Karjalainen",

year = "2005",

doi = "10.3987/COM-05-10535",

language = "English",

volume = "65",

pages = "2783--2790",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "11",

}

TY - JOUR

T1 - Synthesis of benzobicyclo[2.2.1]heptylimidazoles as conformationally constrained adrenergic receptor antagonists

AU - Yli-Kauhaluoma, Jari

AU - Laine, Aki

AU - Ratilainen, Jari

AU - Karjalainen, Arto

PY - 2005

Y1 - 2005

N2 - 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.

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

VL - 65

SP - 2783

EP - 2790

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 11

ER -

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

Abstract

Access to Document

Fingerprint

Cite this