Efficient Catalytic Hydrogenation of N-Unsubstituted Cyclic Imides to Cyclic Amines

被引：20

作者：

Maj, Anna M. ^{[1
]}

Suisse, Isabelle ^{[1
]}

Pinault, Nathalie ^{[2
]}

Robert, Nicolas ^{[2
]}

Agbossou-Niedercorn, Francine ^{[1
]}

机构：

[1] Univ Lille Nord France, CNRS, UCCS, BP 90108, F-59652 Villeneuve Dascq, France

[2] Oril Ind, F-76210 Bolbec, France

来源：

CHEMCATCHEM | 2014年 / 6卷 / 09期

关键词：

cyclic imides; heterogeneous catalysis; hydrogenation; molybdenum; rhodium; ENANTIOSELECTIVE HYDROGENATION; SELECTIVE HYDROGENATION; ACID DERIVATIVES; AMIDES; ESTERS; RUTHENIUM; ALCOHOLS; REDUCTION; COMPLEXES; DESYMMETRIZATION;

D O I：

10.1002/cctc.201402233

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The hydrogenation of N-unsubstituted cyclic imides to the corresponding cyclic amines has been performed selectively with heterogeneous catalysts obtained from rhodium and molybdenum carbonyl precursors. Various substrates were reduced in good to high yields and selectivities. Platinum-based catalysts also proved to be efficient. Furthermore, gram-scale experiments were performed and the catalysts could be recycled.

引用

页码：2621 / 2625

页数：5

共 66 条

[21]

Crabtree S. P, 2005, WO 2005/051907A1, Patent No. 2005051907

[22] Selective Catalytic Monoreduction of Phthalimides and Imidazolidine-2,4-diones [J].

Das, Shoubhik ;

Addis, Daniele ;

Knoepke, Leif R. ;

Bentrup, Ursula ;

Junge, Kathrin ;

Bruekner, Angelika ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9180-9184

[23] Alternative synthesis of the chiral atypical β-adrenergic phenylethanolaminotetraline agonist SR58611A using enantioselective hydrogenation [J].

Devocelle, M ;

Mortreux, A ;

Agbossou, F ;

Dormoy, JR .

TETRAHEDRON LETTERS, 1999, 40 (24) :4551-4554

[24] Catalytic Reductive Transformations of Carboxylic and Carbonic Acid Derivatives Using Molecular Hydrogen [J].

Dub, Pavel A. ;

Ikariya, Takao .

ACS CATALYSIS, 2012, 2 (08) :1718-1741

[25] 1-ARYL-3-AZABICYCLO[3.1.0]HEXANES, A NEW SERIES OF NON-NARCOTIC ANALGESIC AGENTS [J].

EPSTEIN, JW ;

BRABANDER, HJ ;

FANSHAWE, WJ ;

HOFMANN, CM ;

MCKENZIE, TC ;

SAFIR, SR ;

OSTERBERG, AC ;

COSULICH, DB ;

LOVELL, FM .

JOURNAL OF MEDICINAL CHEMISTRY, 1981, 24 (05) :481-490

[26]

Folger E., 2011, ORGANOMETALLICS, V30, P3826

[27]

Gribble GW, 1998, CHEM SOC REV, V27, P395

[28] Hydrogenation of amides by the use of bimetallic catalysts consisting of Group 8 to 10, and Group 6 or 7 metals [J].

Hirosawa, C ;

Wakasa, N ;

Fuchikami, T .

TETRAHEDRON LETTERS, 1996, 37 (37) :6749-6752

[29] Core Modification of Cytisine: A Modular Synthesis [J].

Hirschhaeuser, Christoph ;

Haseler, Claire A. ;

Gallagher, Timothy .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (22) :5162-5165

[30]

ITO M, 2004, Patent No. 2004048327

← 1 2 3 4 5 6 7 →