Anodic methoxylation and acetoxylation of imines and imidates

被引：16

作者：

Baba, D ^{[1
]}

Fuchigami, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Elect Chem, Midori Ku, Yokohama, Kanagawa 2268502, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(03)00548-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Anodic oxidation of cyclic imidates, 2-aryl-2-oxazolines, in methanol provided the corresponding 4-methoxylated products. Anodic alpha-methoxylation and alpha-acetoxylation of open-chain imines derived from glycine esters and benzophenone were also achieved using a bromide ion mediator. On the other hand, anodic a-acetoxylation of CF3-containing imine and imidate was successful without use of the bromine mediator. This is the first example of successful anodic a-substitution of imines and imidates. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：3133 / 3136

页数：4

共 15 条

[1] A new method for the formation of 2,4-disubstituted oxazoles: internal transfer of oxidation state through a molecular framework [J].

Cardwell, KS ;

Hermitage, SA ;

Sjolin, A .

TETRAHEDRON LETTERS, 2000, 41 (21) :4239-4242

[2] ANODIC N-DEARYLATION OF 2-AZETIDINONES [J].

CORLEY, EG ;

KARADY, S ;

ABRAMSON, NL ;

ELLISON, D ;

WEINSTOCK, LM .

TETRAHEDRON LETTERS, 1988, 29 (13) :1497-1500

[3] TOTAL SYNTHESIS OF (+)-CALYCULIN-A [J].

EVANS, DA ;

GAGE, JR ;

LEIGHTON, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9434-9453

[4] NICKEL PEROXIDE DEHYDROGENATION OF OXYGEN-CONTAINING, SULFUR-CONTAINING, AND NITROGEN-CONTAINING HETEROCYCLES [J].

EVANS, DL ;

MINSTER, DK ;

JORDIS, U ;

HECHT, SM ;

MAZZU, AL ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (04) :497-501

[5] ELECTROLYTIC REACTIONS OF FLUOROORGANIC COMPOUNDS .14. REGIOSELECTIVE ANODIC METHOXYLATION OF N-(FLUOROETHYL)AMINES - PREPARATION OF HIGHLY USEFUL FLUOROALKYLATED BUILDING-BLOCKS [J].

FUCHIGAMI, T ;

ICHIKAWA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (03) :607-615

[6] THE CHEMISTRY OF 2-OXAZOLINES (1985-PRESENT) [J].

GANT, TG ;

MEYERS, AI .

TETRAHEDRON, 1994, 50 (08) :2297-2360

[7] Anodic modification of proline derivatives using a lithium perchlorate/nitromethane electrolyte [J].

Kim, S ;

Hayashi, K ;

Kitano, Y ;

Tada, M ;

Chiba, K .

ORGANIC LETTERS, 2002, 4 (21) :3735-3737

[8] ANODIC-OXIDATION OF SCHIFF-BASES .1. OXIDATION OF N-BENZYLIDENE PARA ANISIDINES IN ACETONITRILE [J].

MASUI, M ;

OHMORI, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (12) :1882-&

[9]

MAYER AI, 1996, J ORG CHEM, V61, P8207

[10] 2-PHENYLOXAZOLINES AS CARBOXYLATE PRECURSORS - APPLICATION TO THE SYNTHESIS OF ASYMMETRIC BRANCHED-CHAIN STRUCTURES [J].

MCGARVEY, GJ ;

WILSON, KJ ;

SHANHOLTZ, CE .

TETRAHEDRON LETTERS, 1992, 33 (19) :2641-2644

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