A facile and regioselective synthesis of rimonabant through an enamine-directed 1,3-dipolar cycloaddition

被引：52
作者：
Donohue, Sean R. [1 ,2 ]
Halldin, Christer [2 ]
Pike, Victor W. [1 ]
机构：
[1] NIMH, NIH, Mol Imaging Branch, Bethesda, MD 20892 USA
[2] Karolinska Hosp, Dept Clin Neurosci, Karolinska Inst, S-17176 Stockholm, Sweden
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 17期
基金：
美国国家卫生研究院;
关键词：
CB; receptor; 1,5-diarylpyrazole; rimonabant; 1,3-dipolar cycloaddition;
D O I：
10.1016/j.tetlet.2008.02.132
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rimonabant is a high-potency cannabinoid type-1 (CB1) receptor inverse agonist that has recently been approved in the European Union as a treatment for obesity. Current methods of synthesis require several steps that have long reaction times and/or lack regio-selectivity. Here we present a novel, regioselective synthesis of rimonabant though an enamine-directed 1,3-dipolar cycloaddition. In addition, we present a new and more reactive hydrazonoyl halide for the generation of the requisite nitrile imine dipole. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2789 / 2791
页数：3
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