A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines

被引:8
作者
Zhang, Dan [1 ]
Liu, Junwen [1 ]
Kang, Zhenghui [1 ]
Qiu, Huang [1 ]
Hu, Wenhao [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Key Lab Chiral Mol & Drug Discovery, Guangzhou 510006, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
C; N-CYCLIC AZOMETHINE IMINES; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; EFFICIENT; PRAZIQUANTEL; ANNULATION; ALDEHYDES; YLIDES; SALTS;
D O I
10.1039/c9ob02303h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A rhodium-catalyzed three-component reaction of diazo compounds, anilines and C,N-cyclic azomethine imines via trapping of transient ammonium ylides was developed. This reaction provided a simple and convenient approach for the synthesis of pharmaceutically intriguing tetrahydroisoquinoline derivatives in moderate to good yields (36-85%) with good diastereoselectivities (up to 95 : 5 dr) under mild reaction conditions.
引用
收藏
页码:9844 / 9848
页数:5
相关论文
共 52 条
[1]  
Avendaño C, 2008, MEDICINAL CHEMISTRY OF ANTICANCER DRUGS, P177, DOI 10.1016/B978-0-444-52824-7.00006-8
[2]  
Barbosa-Filho José M., 2006, Rev. bras. farmacogn., V16, P109, DOI 10.1590/S0102-695X2006000100020
[3]   Biomedical Application of Orexin/Hypocretin Receptor Ligands in Neuroscience [J].
Boss, Christoph ;
Brisbare-Roch, Catherine ;
Jenck, Francois .
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (04) :891-903
[4]   Praziquantel: mechanisms of action, resistance and new derivatives for schistosomiasis [J].
Doenhoff, Michael J. ;
Cioli, Donato ;
Utzinger, Juerg .
CURRENT OPINION IN INFECTIOUS DISEASES, 2008, 21 (06) :659-667
[5]   CARDIOVASCULAR EFFECTS OF SUBSTITUTED TETRAHYDROISOQUINOLINES IN RATS [J].
DONG, H ;
LEE, CM ;
HUANG, WL ;
PENG, SX .
BRITISH JOURNAL OF PHARMACOLOGY, 1992, 107 (01) :262-268
[6]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100
[7]  
GONNERT R, 1977, Z PARASITENKD, V52, P129, DOI 10.1007/BF00389899
[8]   Novel Multicomponent Reactions via Trapping of Protic Onium Ylides with Electrophiles [J].
Guo, Xin ;
Hu, Wenhao .
ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (11) :2427-2440
[9]   Recent Advances of Catalytic Asymmetric 1,3-Dipolar Cycloadditions [J].
Hashimoto, Takuya ;
Maruoka, Keiji .
CHEMICAL REVIEWS, 2015, 115 (11) :5366-5412
[10]   Asymmetric Inverse-Electron-Demand 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines: An Umpolung Strategy [J].
Hashimoto, Takuya ;
Omote, Masato ;
Maruoka, Keiji .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (15) :3489-3492