Efficient N-p-methoxyphenyl amine deprotection through anodic oxidation

被引:32
作者
Marin, SD
Martens, T
Mioskowski, C
Royer, J
机构
[1] Univ Strasbourg 1, CNRS, UMR 7514, Chim Bioorgan Lab,Fac Pharm, F-67401 Illkirch Graffenstaden, France
[2] Univ Paris 05, CNRS, UMR 8638, Synth & Struct Mol Interet Pharmacol,Fac Pharm, F-75270 Paris, France
关键词
D O I
10.1021/jo051867o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method of deprotection of N-p-methoxyphenylamines using anodic oxidation in acidic medium is presented. The process furnishes a high yield of amine and is compatible with several oxidable functional groups.
引用
收藏
页码:10592 / 10595
页数:4
相关论文
共 36 条
[1]   The nitro-Mannich reaction and its application to the stereoselective synthesis of 1,2-diamines [J].
Adams, H ;
Anderson, JC ;
Peace, S ;
Pennell, AMK .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9932-9934
[2]   Highly enantioselective reductive amination of simple aryl ketones catalyzed by Ir-f-Binaphane in the presence of titanium(IV) isopropoxide and iodine [J].
Chi, YX ;
Zhou, YG ;
Zhang, XM .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (10) :4120-4122
[3]   Asymmetric synthesis of quaternary α- and β-amino acids and β-lactams via proline-catalyzed Mannich reactions with branched aldehyde donors [J].
Chowdari, NS ;
Suri, JT ;
Barbas, CF .
ORGANIC LETTERS, 2004, 6 (15) :2507-2510
[4]   One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives [J].
Córdova, A .
SYNLETT, 2003, (11) :1651-1654
[5]   A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].
Córdova, A ;
Watanabe, S ;
Tanaka, F ;
Notz, W ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867
[6]   A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].
Córdova, A ;
Notz, W ;
Zhong, GF ;
Betancort, JM ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843
[7]   ANODIC N-DEARYLATION OF 2-AZETIDINONES [J].
CORLEY, EG ;
KARADY, S ;
ABRAMSON, NL ;
ELLISON, D ;
WEINSTOCK, LM .
TETRAHEDRON LETTERS, 1988, 29 (13) :1497-1500
[8]   OXIDATIVE HYDROLYSIS OF GAMMA-THIOACETALATED PHOSPHONIUM SALTS - INFLUENCE OF THE COUNTERION ON THE COURSE OF THE REACTION [J].
CRISTAU, HJ ;
CHABAUD, B ;
CHRISTOL, H .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (11) :2023-2025
[9]   Novel stereocontrolled addition of allylmetal reagents to α-imino esters:: Efficient synthesis of chiral tetrahydroquinoline derivatives [J].
Di Fabio, R ;
Alvaro, G ;
Bertani, B ;
Donati, D ;
Giacobbe, S ;
Marchioro, C ;
Palma, C ;
Lynn, SM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (21) :7319-7328
[10]   Diastereoselective synthesis of fluorinated, seven-membered β-amino acid derivatives via ring-closing metathesis [J].
Fustero, S ;
Bartolomé, A ;
Sanz-Cervera, JF ;
Sánchez-Roselló, M ;
Soler, JG ;
de Arellano, CR ;
Fuentes, AS .
ORGANIC LETTERS, 2003, 5 (14) :2523-2526