Enantioselective synthesis of functionalized fluorinated dihydropyrano [2,3-c]pyrazoles catalyzed by a simple bifunctional diaminocyclohexane-thiourea

被引:31
作者
Zhang, Hong-Fei [1 ]
Ye, Zheng-Qing [1 ]
Zhao, Gang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Synthet Chem Nat Subst, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
Trifluoromethyl; Pyrazoles; Cyclization; Organocatalysis; ONE-POT SYNTHESIS; ASYMMETRIC MICHAEL ADDITION; NAD(+)-DEPENDENT DNA-LIGASE; CARBONYL-COMPOUNDS; DERIVATIVES; HALOGENATION; ACTIVATION; STRATEGIES; MICROWAVE; ANALOGS;
D O I
10.1016/j.cclet.2014.01.034
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Enantioselective synthesis of functionalized fluorinated dihydropyrano[2,3-c]pyrazoles has been achieved via a diaminocyclohexane-thiourea catalyzed cascade Michael addition and Thorpe-Ziegler type cyclization in high yields (up to 98%) with moderate to good enantioselectivity (up to 90% ee). (C) 2014 Gang Zhao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
引用
收藏
页码:535 / 540
页数:6
相关论文
共 57 条
[1]   Cancer chemopreventive effect of phenothiazines and related tri-heterocyclic analogues in the 12-O-tetradecanoylphorbol-13-acetate promoted Epstein-Barr virus early antigen activation and the mouse skin two-stage carcinogenesis models [J].
Azuine, MA ;
Tokuda, H ;
Takayasu, J ;
Enjyo, F ;
Mukainaka, T ;
Konoshima, T ;
Nishino, H ;
Kapadia, GJ .
PHARMACOLOGICAL RESEARCH, 2004, 49 (02) :161-169
[2]   Greener approach towards the facile synthesis of 1,4-dihydropyrano[2,3-c]pyrazol-5-yl cyanide derivatives at room temperature [J].
Balaskar, Ravi S. ;
Gavade, Sandip N. ;
Mane, Madhav S. ;
Shingate, Bapurao B. ;
Shingare, Murlidhar S. ;
Mane, Dhananjay V. .
CHINESE CHEMICAL LETTERS, 2010, 21 (10) :1175-1179
[3]   Specific and potent inhibition of NAD+-dependent DNA ligase by pyridochromanones [J].
Brötz-Oesterhelt, H ;
Knezevic, I ;
Bartel, S ;
Lampe, T ;
Warnecke-Eberz, U ;
Ziegelbauer, K ;
Häbich, D ;
Labischinski, H .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (41) :39435-39442
[4]   Catalytic asymmetric fluorination comes of age [J].
Brunet, Vincent A. ;
O'Hagan, David .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (07) :1179-1182
[5]   Asymmetric Michael addition of α-fluoro-α-phenylsulfonyl ketones to nitroolefins catalyzed by phenylalanine-based bifunctional thioureas [J].
Cui, Hai-Feng ;
Li, Peng ;
Wang, Xiao-Wei ;
Zhu, Shi-Zheng ;
Zhao, Gang .
JOURNAL OF FLUORINE CHEMISTRY, 2012, 133 :120-126
[6]   Enantioselective Synthesis of Functionalized Fluorinated Cyclohexenones via Robinson Annulation Catalyzed by Primary-Secondary Diamines [J].
Cui, Hai-Feng ;
Yang, Ying-Quan ;
Chai, Zhuo ;
Li, Peng ;
Zheng, Chang-Wu ;
Zhu, Shi-Zheng ;
Zhao, Gang .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :117-122
[7]   Highly enantioselective synthesis of α-fluoro-α-nitro esters via organocatalyzed asymmetric Michael addition [J].
Cui, Hai-Peng ;
Li, Peng ;
Wang, Xiao-Wei ;
Chai, Zhuo ;
Yang, Ying-Quan ;
Cai, Yue-Peng ;
Zhu, Shi-Zheng ;
Zhao, Gang .
TETRAHEDRON, 2011, 67 (02) :312-317
[8]   NON-STEROIDAL ANTIINFLAMMATORY AGENTS .1. SYNTHESIS OF 4-HYDROXY-2-OXO-1,2-DIHYDROQUINOLIN-3-YL ALKANOIC ACIDS BY THE WITTIG REACTION OF QUINISATINES [J].
FABER, K ;
STUCKLER, H ;
KAPPE, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) :1177-1181
[9]   Identification of chemically diverse Chk1 inhibitors by receptor-based virtual screening [J].
Foloppe, Nicolas ;
Fisher, Lisa M. ;
Howes, Rob ;
Potter, Andrew ;
Robertson, Alan G. S. ;
Surgenor, Allan E. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (14) :4792-4802
[10]   Organocatalyzed enantioselective synthesis of 6-amino-5-cyanodihydropyrano[2,3-c]pyrazoles [J].
Gogoi, Sanjib ;
Zhao, Cong-Gui .
TETRAHEDRON LETTERS, 2009, 50 (19) :2252-2255