METALATION OF PYRIDINE N-OXIDES AND APPLICATION TO SYNTHESIS

被引:22
作者
MONGIN, O [1 ]
ROCCA, P [1 ]
THOMASDITDUMONT, L [1 ]
TRECOURT, F [1 ]
MARSAIS, F [1 ]
GODARD, A [1 ]
QUEGUINER, G [1 ]
机构
[1] INST NATL SCI APPL ROUEN, IRCOF,CHIM ORGAN FINE & HETEROCYCL LAB,CNRS, URA 1429, F-76131 MONT ST AIGNAN, FRANCE
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 19期
关键词
D O I
10.1039/p19950002503
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regio- and chemi-selective, directed ortho-lithiation of 2-, 2,5- or 3,4-substituted pyridine N-oxides has been achieved with diisopropylamide and butyllithium. Polysubstituted pyridine N-oxides, azaxanthone, and an isomer of orelline have been synthesized by such methods.
引用
收藏
页码:2503 / 2508
页数:6
相关论文
共 23 条
[1]   DIRECT ALKYLATION OF PYRIDINE 1-OXIDES [J].
ABRAMOVI.RA ;
SAHA, M ;
SMITH, EM ;
KNAUS, EE .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (11) :1690-&
[2]   HALOGENATION OF PYRIDINE 1-OXIDES [J].
ABRAMOVITCH, RA ;
CAMPBELL, J ;
KNAUS, EE ;
SILHANKO.A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (06) :1367-1371
[3]   SYNTHESIS OF 1-HYDROXY-2-PYRIDINETHIONES, 1-HYDROXY-2-PYRIDONES AND HALOPYRIDINE 1-OXIDES - REACTIONS OF LITHIOPYRIDINE 1-OXIDES [J].
ABRAMOVITCH, RA ;
KNAUS, EE .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (06) :989-+
[4]   DIRECT ACYLATION OF PYRIDINE 1-OXIDES [J].
ABRAMOVITCH, RA ;
SMITH, EM ;
COUTTS, RT .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (23) :3584-+
[5]  
ABRAMOVITCH RA, 1974, PYRIDINE ITS DERIV 2, P1
[6]  
ANTKOWIAK WZ, 1979, TETRAHEDRON LETT, P1931
[7]   ORTHO LITHIATION OF TERTIARY BENZAMIDES [J].
BEAK, P ;
BROWN, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (10) :1823-1824
[8]  
EPSZTAJN J, 1986, J CHEM RES-S, P18
[9]   APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESES .1. REACTIONS OF THE N,N-DIALKYLPYRIDYLCARBOXYLIC AMIDES WITH LITHIUM AMIDES - REGIOSELECTIVE LITHIATION OF N,N-DIISOPROPYLPYRIDYLCARBOXYLIC AMIDES, A USEFUL METHOD FOR SYNTHESIS OF 2,3- AND 3,4-DISUBSTITUTED PYRIDINES [J].
EPSZTAJN, J ;
BERSKI, Z ;
BRZEZINSKI, JZ ;
JOZWIAK, A .
TETRAHEDRON LETTERS, 1980, 21 (49) :4739-4742
[10]   SYNTHESIS OF ORTHO-SUBSTITUTED AMINOPYRIDINES - METALATION OF PIVALOYLAMINO DERIVATIVES [J].
ESTEL, L ;
LINARD, F ;
MARSAIS, F ;
GODARD, A ;
QUEGUINER, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :105-112