Divergent Syntheses of 2-Aminonicotinonitriles and Pyrazolines by Copper-Catalyzed Cyclization of Oxime Ester

被引:133
作者
Wu, Qifan
Zhang, Yan
Cui, Sunliang [1 ]
机构
[1] Zhejiang Univ, Inst Mat Med, Hangzhou 310058, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
ORIENTED ORGANIC-SYNTHESIS; H BOND ACTIVATION; EFFICIENT SYNTHESIS; PARALLEL SYNTHESIS; DRUG DISCOVERY; CONSTRUCTION; ANTAGONISTS; AMINATION; ALDEHYDES; PYRIDINES;
D O I
10.1021/ol500094w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed cyclization of an oxime ester toward divergent heterocycle synthesis is reported. Oxime ester serves as an enamine precursor to cyclize with malononitrile and aldehydes for access to 2-aminonicotinonitriles in a one-pot reaction, while cyclizing with N-sulfonylimines leads to synthesis of pyrazolines.
引用
收藏
页码:1350 / 1353
页数:4
相关论文
共 43 条
[1]   DAST-Mediated Cyclization of α,α-Disubstituted-α-acylaminoketones: Efficient and Divergent Synthesis of Unprecedented Heterocycles [J].
Bigot, Aurelien ;
Blythe, Judith ;
Pandya, Chirag ;
Wagner, Trixie ;
Loiseleur, Olivier .
ORGANIC LETTERS, 2011, 13 (02) :192-195
[2]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[3]   A Divergent and Selective Synthesis of Isomeric Benzoxazoles from a Single N-Cl Imine [J].
Chen, Cheng-yi ;
Andreani, Teresa ;
Li, Hongmei .
ORGANIC LETTERS, 2011, 13 (23) :6300-6303
[4]  
Chichibabin A.E., 1914, J RUSS PHYS CHEM SOC, V46, P1216
[5]   An Expedient and Divergent Tandem One-Pot Synthesis of Pyrimidin-2,4-diones Using the Blaise Reaction Intermediate [J].
Chun, Yu Sung ;
Xuan, Zi ;
Kim, Ju Hyun ;
Lee, Sang-gi .
ORGANIC LETTERS, 2013, 15 (12) :3162-3165
[6]   Parallel synthesis of strongly fluorescent polysubstituted 2,6-dicyanoanilines via microwave-promoted multicomponent reaction [J].
Cui, SL ;
Lin, XF ;
Wang, YG .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2866-2869
[7]   Rh(III)-catalyzed C-H activation/cycloaddition of benzamides and methylenecyclopropanes: divergence in ring formation [J].
Cui, Sunliang ;
Zhang, Yan ;
Wu, Qifan .
CHEMICAL SCIENCE, 2013, 4 (09) :3421-3426
[8]   Rh(III)-catalyzed C-H activation/[4+3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones [J].
Cui, Sunliang ;
Zhang, Yan ;
Wang, Dahai ;
Wu, Qifan .
CHEMICAL SCIENCE, 2013, 4 (10) :3912-3916
[9]   Pd-Catalyzed C4-Olefination of Oxazoles via C-H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives [J].
Cui, Sunliang ;
Wojtas, Lukasz ;
Antilla, Jon C. .
ORGANIC LETTERS, 2011, 13 (19) :5040-5043
[10]   Divergent C-H Functionalizations Directed by Sulfonamide Pharmacophores: Late-Stage Diversification as a Tool for Drug Discovery [J].
Dai, Hui-Xiong ;
Stepan, Antonia F. ;
Plummer, Mark S. ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) :7222-7228