A facile and efficient synthesis of fully substituted pyridin-2(1H)-ones from α-oxoketene-S,S-acetals

被引:6
作者
Yang, Xiuyun [1 ]
Cheng, Yanyan [1 ]
Zhao, Fei [3 ]
Li, Yunhui [1 ]
Ding, Yuanli [1 ]
Liang, Yongjiu [2 ]
Gan, Fengjiao [1 ]
Dong, Dewen [2 ]
机构
[1] Changchun Univ Sci & Technol, Sch Chem & Environm Engn, Changchun 130022, Peoples R China
[2] Chinese Acad Sci, Changchun Inst Appl Chem, Changchun 130022, Peoples R China
[3] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
ALPHA-CARBAMOYL KETENE-S; S-ACETALS; ONE-POT SYNTHESIS; KETENE DITHIOACETALS; VILSMEIER REACTION; MICHAEL ADDITION; ANNULATION; STRATEGY; ODORLESS; ACID; THIOACETALIZATION;
D O I
10.1016/j.tet.2011.08.066
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient synthesis of fully substituted pyridin-2(1H)-ones has been developed by the reaction of readily available alpha-oxoketene-S,S-acetals with malononitrile in the presence of sodium methoxide in methanol under reflux. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8343 / 8347
页数:5
相关论文
共 65 条
[1]  
AGGARWAL V, 1982, SYNTHESIS-STUTTGART, P214
[2]   A convenient preparation of 2-aroyl-3,3-bis(alkylsulfanyl)acrylaldehydes and their application in the synthesis of 5-aroyl-2-oxo-1,2-dihydro-2-pyridinecarbonitriles [J].
Anabha, ER ;
Asokan, CV .
SYNTHESIS-STUTTGART, 2006, (01) :151-155
[3]   Synthesis routes towards the farnesyl protein transferase inhibitor ZARNESTRA™ [J].
Angibaud, PR ;
Venet, MG ;
Filliers, W ;
Broeckx, R ;
Ligny, YA ;
Muller, P ;
Poncelet, VS ;
End, DW .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) :479-486
[4]  
[Anonymous], CHEM BER
[5]   Total synthesis of pyridovericin: Studies toward the biomimetic synthesis of pyridomacrolidin [J].
Baldwin, JE ;
Adlington, RM ;
Conte, A ;
Irlapati, NR ;
Marquez, R ;
Pritchard, GJ .
ORGANIC LETTERS, 2002, 4 (13) :2125-2127
[6]   The formation and reactions of imino-com-pounds Part I Condensation of ethyl cyano-acetate with its sodium derivative [J].
Baron, H ;
Remfry, FGP ;
Thorpe, JF .
JOURNAL OF THE CHEMICAL SOCIETY, 1904, 85 :1726-1761
[7]   NUCLEOPHILIC-ADDITION TO OLEFINS - KINETICS AND MECHANISM [J].
BERNASCONI, CF .
TETRAHEDRON, 1989, 45 (13) :4017-4090
[8]   THE CF3CH2O- ADDUCTS OF ALPHA-NITRO-BETA-(2,2,2-TRIFLUOROETHOXY)STILBENE AND BETA-METHOXY-ALPHA-NITROSTILBENE, AND THE MEO- ADDUCT OF BETA-METHOXY-ALPHA-NITROSTILBENE - KINETICS OF COMPETITION BETWEEN PROTONATION AND ACID-CATALYZED ALKOXIDE ION DEPARTURE [J].
BERNASCONI, CF ;
SCHUCK, DF ;
KETNER, RJ ;
EVENTOVA, I ;
RAPPOPORT, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) :2719-2725
[9]   Hydrolysis of α-alkyl-α-(methylthio)methylene Meldrum's acids.: A kinetic and computational investigation of steric effects [J].
Bernasconi, Claude F. ;
Brown, Shoshana D. ;
Ali, Mahammad ;
Rappoport, Zvi ;
Yamataka, Hiroshi .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4795-4802
[10]   [5C+1S] annulation: A facile and efficient synthetic route toward functionalized 2,3-dihydrothiopyran-4-ones [J].
Bi, XH ;
Dong, DW ;
Li, Y ;
Liu, Q ;
Zhang, Q .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) :10886-10889