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

页码：5093 / 5099

页数：7

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