Oxidation of chiral non-racemic pyridinium salts to enantiopure 2-pyridone and 3-alkyl-2-pyridones

被引：23

作者：

Gnecco, D ^{[1
]}

Marazano, C ^{[1
]}

Enríquez, RG ^{[1
]}

Terán, JL ^{[1
]}

Sánchez, MD ^{[1
]}

Galindo, A ^{[1
]}

机构：

[1] Univ Autonoma Puebla, Inst Ciencias, Ctr Quim, BUAP Cd, Puebla 72570, Mexico

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(98)00151-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Oxidation of chiral non-racemic pyridinium salt 1a and 3-alkyl pyridinium salts 1b and 1c with potassium ferricyanide in an alkaline medium provides a short and practical access to enantiomerically pure 2-pyridone (2a) and 3-alkyl-2-pyridones (2b and 2c) in high yields and very good regioselectivity from derivatives 1(b-c). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：2027 / 2029

页数：3

共 14 条

[1] Synthesis of enantiopure piperidines. Total synthesis of (2R,6S)-2-methyl-6-propylpiperidine [(-)-dihydropinidine] [J].

Amat, M ;

Llor, H ;

Hidalgo, J ;

Hernandez, A ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :977-980

[2] SYNTHESES OF AN ANTIPSYCHOTIC PYRROLO[2,3-G]ISOQUINOLINE FROM ARECA ALKALOIDS [J].

COFFEN, DL ;

HENGARTNER, U ;

KATONAK, DA ;

MULLIGAN, ME ;

BURDICK, DC ;

OLSON, GL ;

TODARO, LJ .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (26) :5109-5113

[3]

COOKSEY CJ, 1968, J CHEM SOC B, V10, P1191

[4]

FUJII T, 1973, CHEM PHARM BULL, V20, P2695

[5]

GENISSON Y, 1992, SYNLETT, P431

[6] Synthesis of tetrahydroquinolines, hexahydrobenzoindolizines and an aryl phosphonate linker for the generation of catalytic antibodies [J].

GonzalezBello, C ;

Abell, C ;

Leeper, FJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (07) :1017-1024

[7] The tandem Pummerer-isomunchnone route to (+/-)-pumiliotoxin C [J].

Kuethe, JT ;

Padwa, A .

TETRAHEDRON LETTERS, 1997, 38 (09) :1505-1508

[8] Selective reductions of 1-methyl-4-phenyl-2-pyridone [J].

Mabic, S ;

Castagnoli, N .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :309-313

[9] A NOVEL ROUTE TO CHIRAL, NONRACEMIC 1-ALKYL-SUBSTITUTED AND 1-ARYL-SUBSTITUTED TETRAHYDROISOQUINOLINES - SYNTHESIS OF (-)-SALSOLIDINE AND (+)-CRYPTOSTYLINE-II [J].

MUNCHHOF, MJ ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7086-7087

[10] AN ASYMMETRIC ROUTE TO CHIRAL, NONRACEMIC 2-SUBSTITUTED PIPERIDINES - SYNTHESIS OF (-)-PIPECOLINE, (+)-CONIINE, AND (-)-CONICEINE [J].

MUNCHHOF, MJ ;

MEYERS, AI .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22) :7084-7085

← 1 2 →