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

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

Research output: Contribution to journalArticleScientificpeer-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 languageEnglish
Pages (from-to)2783-2790
JournalHeterocycles
Volume65
Issue number11
DOIs
Publication statusPublished - 2005
MoE publication typeA1 Journal article-refereed

Fingerprint

Adrenergic Antagonists
Adrenergic Agents
Medetomidine
Adrenergic Agonists
Cycloaddition
Cycloaddition Reaction
Isomers
imidazole
atipamezole
benzyne

Cite this

Yli-Kauhaluoma, Jari ; Laine, Aki ; Ratilainen, Jari ; Karjalainen, Arto. / Synthesis of benzobicyclo[2.2.1]heptylimidazoles as conformationally constrained adrenergic receptor antagonists. In: Heterocycles. 2005 ; Vol. 65, No. 11. pp. 2783-2790.
@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’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",

}

Synthesis of benzobicyclo[2.2.1]heptylimidazoles as conformationally constrained adrenergic receptor antagonists. / Yli-Kauhaluoma, Jari; Laine, Aki; Ratilainen, Jari; Karjalainen, Arto.

In: Heterocycles, Vol. 65, No. 11, 2005, p. 2783-2790.

Research output: Contribution to journalArticleScientificpeer-review

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 -