A General Palladium-Catalyzed Carbonylative Synthesis of 2-Alkylbenzoxazinones from 2-Bromoanilines and Acid Anhydrides

被引：50
作者：
Wu, Xiao-Feng [1 ,2 ]
Neumann, Helfried [2 ]
Beller, Matthias [2 ]
机构：
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 40期
关键词：
bromoanilines; benzoxazinones; carbonylation; heterocycles; palladium; ONE-POT SYNTHESIS; C-H ACTIVATION; ARYL HALIDES; 3-COMPONENT SYNTHESIS; HETEROARYL BROMIDES; COUPLING REACTIONS; HETEROCYCLES; CONVENIENT; INHIBITORS; EFFICIENT;
D O I：
10.1002/chem.201202142
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(C), its (O)K! An efficient palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones has been developed (see scheme). By starting from 2-bromoanilines and acid anhydrides, the corresponding products were isolated in good yields. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：12599 / 12602
页数：4
相关论文
共 65 条
[1]   Palladium-catalysed carbonylation of 4-substituted 2-iodoaniline derivatives:: carbonylative cyclisation and aminocarbonylation [J].
Acs, Peter ;
Muller, Erno ;
Rangits, Gabor ;
Lorand, Tamas ;
Kollar, Laszlo .
TETRAHEDRON, 2006, 62 (51) :12051-12056
[2]  
[Anonymous], 2009, ANGEW CHEM
[3]  
[Anonymous], 2010, ANGEW CHEM
[4]   THE MECHANISM OF THE SCHMIDT REACTION WITH ORTHO-BENZOYLBENZOIC ACID [J].
ARCUS, CL ;
COOMBS, MM .
JOURNAL OF THE CHEMICAL SOCIETY, 1953, (NOV) :3698-3700
[5]   REACTIONS OF CYCLIC ANHYDRIDES .11. A FACILE APPROACH TO PYRROLO-3, 1-BENZOXAZINONES VIA ANILIC ACIDS [J].
BALSUBRAMANIYAN, V ;
ARGADE, NP .
TETRAHEDRON LETTERS, 1986, 27 (22) :2487-2488
[6]   SYNTHESIS OF [1]BENZOTHIENO[3,2-DD]PYRIMIDINE DERIVATIVES [J].
BECK, JR ;
YAHNER, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (14) :2450-2452
[7]   PROGRESS IN HYDROFORMYLATION AND CARBONYLATION [J].
BELLER, M ;
CORNILS, B ;
FROHNING, CD ;
KOHLPAINTNER, CW .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 104 (01) :17-85
[8]   Palladium-Catalyzed Carbonylation Reactions of Alkenes and Alkynes [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
CHEMCATCHEM, 2009, 1 (01) :28-41
[9]   Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].
Brennfuehrer, Anne ;
Neumann, Helfried ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133
[10]   Palladium/di-1-adamantyl-n-butylphosphine-catalyzed reductive carbonylation of aryl and vinyl halides [J].
Brennfuhrer, Anne ;
Neumann, Helfried ;
Klaus, Stefan ;
Riermeier, Thomas ;
Almena, Juan ;
Beller, Matthias .
TETRAHEDRON, 2007, 63 (27) :6252-6258
1234567