Synthesis of 5-and 6-(6-chloro-3-pyridyl)-2-azabicyclo[2.2.0]hexanes. Epibatidine analogs

被引：17

作者：

Krow, GR ^{[1
]}

Yuan, J

Huang, QL

Meyer, MD

Anderson, DJ

Campbell, JE

Carroll, PJ

机构：

[1] Temple Univ, Dept Chem, Philadelphia, PA 19122 USA

[2] Abbott Labs, Div Pharmaceut Prod, Neurosci Res, Abbott Pk, IL 60064 USA

[3] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 47期

关键词：

Heck reaction; stereocontrol; bicyclic heterocyclic compounds; amines;

D O I：

10.1016/S0040-4020(00)00896-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthetic routes to vicinal-6-(6-Cl-3-pyridyl)- and distal-5-(6-Cl-3-pyridyl)-2-azabicyclo-[2.2.0]hexane analogs of the potent nicotinic receptor agonist epibatidine are described. Both exo-regioisomers are available from a readily available 2-azabicyclo[2.2.0]hex-5-ene by way of stereoselective reductive Heck addition of the 6-Cl-3-pyridyl moiety. Stereochemical inversion of the 6- and 5-aryl groups provides entry to the endo isomers. (C) 2000 Elsevier Science Ltd. All rights reserved.

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收藏

页码：9233 / 9239

页数：7

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