An improved synthetic protocol and plausible mechanism in forming acetylpyridines from 2,6-dicarbethoxypyridine

被引:8
作者
Asma, Maliha [1 ,2 ,3 ]
Adewuyi, Sheriff [1 ,2 ]
Kuang, Xiaofei [1 ,2 ]
Badshah, Amin [3 ]
Sun, Wen-Hua [1 ,2 ]
机构
[1] Chinese Acad Sci, Inst Chem, Key Lab Engn Plast, Beijing 100080, Peoples R China
[2] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
[3] Quaid I Azam Univ, Dept Chem, Islamabad 45320, Pakistan
关键词
2-Carbethoxy-6-acetylpyridine; 2,6-diacetylpyridine; 2,6-dicarbethoxypyridine; Claisen ester condensation; anti-Claisen reaction;
D O I
10.2174/157017808784049515
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Carbethoxy-6-acetylpyridine and 2,6-diacetylpyridine were transformed in good yields from the reaction of 2,6-dicarbethoxypyridine and EtOAc in the presence of sodium along with/without an equivalent of ethanol to sodium in toluene. The beta-keto esters, the intermediates in the transformation of beta-keto carboxylate into acetyl group, were isolated for understanding the plausible mechanism.
引用
收藏
页码:296 / 299
页数:4
相关论文
共 23 条
[1]   Nickel(II) complexes chelated by 2-quinoxalinyl-6-iminopyridines: Synthesis, crystal structures and ethylene oligomerization [J].
Adewuyi, Sherrif ;
Li, Gang ;
Zhang, Shu ;
Wang, Wenqing ;
Hao, Peng ;
Sun, Wen-Hua ;
Tang, Ning ;
Yi, Jianjun .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (16) :3532-3541
[2]   SOME DISUBSTITUTED PYRIDINES RELATED TO 2,6-LUTIDINE [J].
BARNES, RA ;
FALES, HM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (15) :3830-3831
[3]  
BRICH W, 1990, BEILSTEIN HDB OR 4 5, V22, P128
[4]   Novel olefin polymerization catalysts based on iron and cobalt [J].
Britovsek, GJP ;
Gibson, VC ;
Kimberley, BS ;
Maddox, PJ ;
McTavish, SJ ;
Solan, GA ;
White, AJP ;
Williams, DJ .
CHEMICAL COMMUNICATIONS, 1998, (07) :849-850
[5]  
Britovsek GJP, 2000, CHEM-EUR J, V6, P2221, DOI 10.1002/1521-3765(20000616)6:12<2221::AID-CHEM2221>3.3.CO
[6]  
2-L
[7]   Iron and cobalt ethylene polymerization catalysts bearing 2,6-bis(imino)pyridyl ligands:: Synthesis, structures, and polymerization studies [J].
Britovsek, GJP ;
Bruce, M ;
Gibson, VC ;
Kimberley, BS ;
Maddox, PJ ;
Mastroianni, S ;
McTavish, SJ ;
Redshaw, C ;
Solan, GA ;
Strömberg, S ;
White, AJP ;
Williams, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (38) :8728-8740
[8]   Chromium(III) complexes ligated by 2-(1-isopropyl-2-benzimidazolyl)-6-(1-(arylimino)ethyl) pyridines: Synthesis, characterization and their ethylene oligomerization and polymerization [J].
Chen, Yanjun ;
Zuo, Weiwei ;
Hao, Peng ;
Zhang, Shu ;
Gao, Kun ;
Sun, Wen-Hua .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2008, 693 (04) :750-762
[9]  
Claisen L., 1887, BER DTSCH CHEM GES, V20, P651
[10]  
DEKIMPE N, 1987, SYNTHESIS-STUTTGART, P188