Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides

被引:16
作者
Fukuzawa, Hiroko [1 ]
Ura, Yasuyuki [1 ]
Kataoka, Yasutaka [1 ]
机构
[1] Nara Womens Univ, Fac Sci, Dept Chem, Nara 6308506, Japan
关键词
Reduction; Deprotection; N-Alkoxyamides; N-Hydroxyamides; Hydroxamic acids; Ruthenium; MATRIX-METALLOPROTEINASE INHIBITORS; DIELS-ALDER REACTIONS; HYDROXAMIC ACIDS; WEINREB AMIDES; O BONDS; ACRYLATE DIMERIZATION; ORGANIC-CHEMISTRY; COMPLEXES; CLEAVAGE; METHYLAMIDES;
D O I
10.1016/j.jorganchem.2011.08.026
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides was found to afford corresponding amides in good to high yields. A simple RuCl3/Zn-Cu/alcohol system, without the addition of any other ligands, exhibited a high catalytic activity, and therefore the present reaction does not require a stoichiometric amount of metals or metal complexes as reductants. When beta-substituted-alpha,beta-unsaturated N-methoxyamides were employed as substrates, concurrent hydrogenation of the olefin moiety proceeded slowly with deprotection of the methoxy group. In the reduction of N-hydroxyamides, the alcoholic solvent was found to function as a hydrogen donor. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:3643 / 3648
页数:6
相关论文
共 54 条
[1]   NORBORNADIENE-METAL COMPLEXES AND SOME RELATED COMPOUNDS [J].
ABEL, EW ;
BENNETT, MA ;
WILKINSON, G .
JOURNAL OF THE CHEMICAL SOCIETY, 1959, (NOV) :3178-3182
[2]  
Albers M. O., 1989, INORG SYNTH, V26
[3]   Reductive deprotection of allyl, benzyl and sulfonyl substituted alcohols, amines and amides using a naphthalene-catalysed lithiation [J].
Alonso, E ;
Ramon, DJ ;
Yus, M .
TETRAHEDRON, 1997, 53 (42) :14355-14368
[4]  
Arkaitz C., 2008, CHEM-EUR J, V14, P3527
[5]   CHEMISTRY OF HYDROXAMIC ACIDS AND N-HYDROXYIMIDES [J].
BAUER, L ;
EXNER, O .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (06) :376-384
[6]  
Bauer L., 1974, Angew. Chem, V86, P419
[7]   ARENE RUTHENIUM(II) COMPLEXES FORMED BY DEHYDROGENATION OF CYCLOHEXADIENES WITH RUTHENIUM(III) TRICHLORIDE [J].
BENNETT, MA ;
SMITH, AK .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1974, (02) :233-241
[8]  
Boukhris S., 1996, TETRAHEDRON LETT, V37, P179
[9]   Titanocene(III) Chloride-Mediated Reductions of Oxazines, Hydroxamic Acids, and N-Hydroxy Carbamates [J].
Cesario, Cara ;
Tardibono, Lawrence P., Jr. ;
Miller, Marvin J. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) :448-451
[10]   Design and synthesis of piperazine-based matrix metalloproteinase inhibitors [J].
Cheng, MY ;
De, B ;
Pikul, S ;
Almstead, NG ;
Natchus, MG ;
Anastasio, MV ;
McPhail, SJ ;
Snider, CE ;
Taiwo, YO ;
Chen, LY ;
Dunaway, CM ;
Gu, F ;
Dowty, ME ;
Mieling, GE ;
Janusz, MJ ;
Wang-Weigand, S .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (03) :369-380