SYNTHETIC APPLICATIONS OF N-N LINKED HETEROCYCLES .6. REGIOSPECIFIC NUCLEOPHILIC-ATTACK AT THE GAMMA-POSITION OF 1-(2,6-DIMETHYL-4-OXO-1,4-DIHYDRO-1-PYRIDYL)PYRIDINIUM COMPOUNDS - NOVEL SYNTHESIS OF 4-SUBSTITUTED PYRIDINES

被引:38
作者
KATRITZKY, AR [1 ]
BELTRAMI, H [1 ]
KEAY, JG [1 ]
ROGERS, DN [1 ]
SAMMES, MP [1 ]
LEUNG, CWF [1 ]
LEE, CM [1 ]
机构
[1] UNIV HONG KONG,DEPT CHEM,HONG KONG,HONG KONG
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1979年 / 18卷 / 10期
关键词
D O I
10.1002/anie.197907922
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Syntheses of 4‐substituted pyridines 3 are always of interest. In the pyridinium ion 1 positions 2 and 6 are sterically shielded; it therefore reacts at the activated position 4 with C, N and S nuleophiles in high yields to give 2, which is readily cleaved to 3 and 4, or decomposes to these products. (Figure Presented.) Copyright © 1979 by Verlag Chemie, GmbH, Germany
引用
收藏
页码:792 / 793
页数:2
相关论文
共 14 条
[1]  
Arens JF, 1942, RECL TRAV CHIM PAY-B, V61, P59
[2]   ALKYL NITRATE NITRATION OF ACTIVE METHYLENE COMPOUNDS .9. NITRATION OF ALKYL SUBSTITUTED HETEROCYCLIC-COMPOUNDS [J].
FEUER, H ;
LAWRENCE, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (23) :3662-&
[3]   ALKYL NITRATE NITRATION OF ACTIVE METHYLENE COMPOUNDS .10. COURSE OF ALKYL NITRATE NITRATION WITH ISOPROPYLPYRIDINES - FORMATION OF 2,3-BIS(PYRIDYL)-2,3-DIMETHYLBUTANES [J].
FEUER, H ;
DOTY, J ;
LAWRENCE, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (03) :417-422
[4]  
GRANDBERG II, 1968, KHIM FARM ZH, V2, P24
[5]   PREPARATION OF 4-ARYL-PYRIDINES AND 4-HETEROARYL-PYRIDINES - REGIOSPECIFIC NUCLEOPHILIC ATTACK GAMMA TO A QUATERNARY NITROGEN ATOM [J].
KATRITZKY, AR ;
BELTRAMI, H ;
SAMMES, MP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (03) :137-137
[6]  
KATRITZKY AR, UNPUBLISHED
[7]   SYNTHESES OF HETEROCYCLIC COMPOUNDS .2. N-ARYLAZOLES BY ULLMANN CONDENSATION [J].
KHAN, MA ;
POLYA, JB .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (01) :85-&
[8]   SELECTIVE ACYLATION OF 2,4-LUTIDINE AT ITS 2-METHYL AND 4-METHYL GROUPS [J].
LEVINE, R ;
DIMMIG, DA ;
KADUNCE, WM .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (26) :3834-3837
[9]   THE SYNTHESIS OF NITROGEN-CONTAINING KETONES .7. A STUDY OF THE ACYLATION OF 4-PICOLINE [J].
OSUCH, C ;
LEVINE, R .
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (08) :939-943
[10]   THE USE OF ORGANOLITHIUM COMPOUNDS TO EFFECT THE ALKYLATION OF 2-PICOLINE AND 4-PICOLINE [J].
OSUCH, C ;
LEVINE, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (08) :1723-1725