A novel route to new carbonyl derivatives of cinchonine and cinchonidine

被引：4

作者：

Dodin, G

Cordier, C

Menager, L

Bourzegue, A

Blais, JC

机构：

[1] Univ Denis Diderot, ITODYS, CNRS URA 34, F-75005 Paris, France

[2] Univ Paris 06, Lab Chim Struct & Biol, F-75005 Paris, France

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 21期

关键词：

D O I：

10.1039/a803854f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cinchonine and cinchonidine are readily transformed to their corresponding N-oxides by the action of MMPP in acetonitrile-bicarbonate buffer. Methylation of the N-oxides by iodamethane in dichloromethane leads, under mild conditions, to the formation of a unique enol stabilized by intramolecular hydrogen bonding. In water the enol form tautomerizes to its parent keto derivatives. The reaction has been extended to quinine and quinidine.

引用

收藏

页码：3619 / 3621

页数：3

相关论文

共 11 条

[1]

[Anonymous], TETRAHEDRON LETT

[2] Amine oxides. VII. The thermal decomposition of the N-Oxides of N-Methylazacycloalkanes [J].

Cope, Arthur C. ;

Lebel, Norman A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (17) :4656-4662

[3] THE APPLICATION OF A MECHANISTIC MODEL LEADS TO THE EXTENSION OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION TO ALLYLIC 4-METHOXYBENZOATES AND CONFORMATIONALLY RELATED AMINE AND HOMOALLYLIC ALCOHOL DERIVATIVES [J].

COREY, EJ ;

GUZMANPEREZ, A ;

NOE, MC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10805-10816

[4] THE ORIGIN OF HIGH ENANTIOSELECTIVITY IN THE DIHYDROXYLATION OF OLEFINS USING OSMIUM TETRAOXIDE AND CINCHONA ALKALOID CATALYSTS [J].

COREY, EJ ;

NOE, MC ;

SARSHAR, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (09) :3828-3829

[5] KINETIC RESOLUTION BY ENANTIOSELECTIVE DIHYDROXYLATION OF SECONDARY ALLYLIC 4-METHOXYBENZOATE ESTERS USING A MECHANISTICALLY DESIGNED CINCHONA ALKALOID CATALYST [J].

COREY, EJ ;

NOE, MC ;

GUZMANPEREZ, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10817-10824

[6] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR AND MOLECULAR-ORBITAL APPROACH [J].

DIJKSTRA, GDH ;

KELLOGG, RM ;

WYNBERG, H .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6121-6131

[7]

GENNE P, 1995, ANTI-CANCER DRUG DES, V10, P103

[8]

GENNE P, 1992, CANCER RES, V52, P2797

[9]

GENNE P, 1994, LEUKEMIA, V8, P1601

[10] C-13 NUCLEAR MAGNETIC-RESONANCE SPECTRA OF CINCHONA ALKALOIDS [J].

MORELAND, CG ;

PHILIP, A ;

CARROLL, FI .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (16) :2413-2416