Rh(l)-catalyzed direct ortho-alkenylation of aromatic ketimines with alkynes and its application to the synthesis of isoquinoline derivatives

被引:185
作者
Lim, SG [1 ]
Lee, JH [1 ]
Moon, CW [1 ]
Hong, JB [1 ]
Jun, CH [1 ]
机构
[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
关键词
D O I
10.1021/ol035083d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel synthetic methods of both ortho-alkenylated aromatic ketones and isoquinoline derivatives have been developed through the Rh(I)-catalyzed direct ortho-alkenylation of common aromatic ketimines with alkynes. Furthermore, a highly efficient one-pot synthesis of isoquinoline derivatives was achieved by simply mixing aromatic ketone, benzylamine, and alkyne under a Rh(I) catalyst.
引用
收藏
页码:2759 / 2761
页数:3
相关论文
共 21 条
[1]   Convenient preparation of mononuclear and dinuclear ruthenium hydride complexes for catalytic application [J].
Busch, S ;
Leitner, W .
CHEMICAL COMMUNICATIONS, 1999, (22) :2305-2306
[2]   Transition metal catalysed alkylation of pyridines and indoles [J].
Grigg, R ;
Savic, V .
TETRAHEDRON LETTERS, 1997, 38 (32) :5737-5740
[3]   Ruthenium-catalysed ortho vinylation of aromatic ketones with alkynes;: unexpected cyclopentaannulation [J].
Harris, PWR ;
Rickard, CEF ;
Woodgate, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 589 (02) :168-179
[4]   Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes [J].
Huang, QH ;
Hunter, JA ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3437-3444
[5]  
Jun CH, 2000, ANGEW CHEM INT EDIT, V39, P3440, DOI 10.1002/1521-3773(20001002)39:19<3440::AID-ANIE3440>3.0.CO
[6]  
2-1
[7]  
Jun CH, 2002, CHEM-EUR J, V8, P485, DOI 10.1002/1521-3765(20020118)8:2<485::AID-CHEM485>3.3.CO
[8]  
2-T
[9]   A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage [J].
Kakiuchi, F ;
Kan, S ;
Igi, K ;
Chatani, N ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1698-1699
[10]   Ruthenium-catalyzed addition of olefinic C-H bonds in conjugate enones to acetylenes to give conjugate dienones [J].
Kakiuchi, F ;
Uetsuhara, T ;
Tanaka, Y ;
Chatani, N ;
Murai, S .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2002, 182 (01) :511-514