Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide

被引：42
|
作者：
Bantreil, Xavier [1 ]
Kanfar, Nasreddine [1 ]
Gehin, Nicolas [1 ]
Golliard, Ethan [1 ]
Ohlmann, Pauline [1 ]
Martinez, Jean [1 ]
Lamaty, Frederic [1 ]
机构：
[1] Univ Montpellier 2, ENSCM, Inst Biomol Max Mousseron, UMR 5247,CNRS,UM 1, F-34095 Montpellier 5, France
来源：
TETRAHEDRON | 2014年 / 70卷 / 34期
关键词：
Iron; Homogeneous catalysis; Amides; Oxidation; Green chemistry; AMINE HYDROCHLORIDE SALTS; AMIDE SYNTHESIS; OXIDATIVE AMIDATION; INTRAMOLECULAR CYCLIZATION; MOLECULAR-IODINE; ALCOHOLS; ALDEHYDES; ACIDS; SECONDARY; PEPTIDES;
D O I：
10.1016/j.tet.2014.06.001
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and user-friendly method to yield benzamides from primary and secondary amines and various benzylic alcohols in the presence of a cheap iron salt (FeCl2 center dot 4H(2)O) and tert-butylhydroperoxide (70% in water) as a stoichiometric oxidant is described. Control experiments indicated that this reaction might involve radical species. This method proved to be general, generating a family of 30 benzamides and was applied to the preparative synthesis of anti-anxiety drug moclobemide. (C) 2014 Published by Elsevier Ltd.
引用
收藏
页码：5093 / 5099
页数：7
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