Access to π-conjugated azaindole derivatives via rhodium(III)-catalyzed cascade reaction of azaindoles and diazo compounds

被引:25
作者
Liu, Chen-Fei [1 ]
Zhang, Guo-Tai [1 ]
Sun, Jun-Shu [1 ]
Dong, Lin [1 ]
机构
[1] Sichuan Univ, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, Chengdu 610041, Peoples R China
关键词
C-H ACTIVATION; ACTIVE CARBAZOLE ALKALOIDS; 7-AZAINDOLES; FUNCTIONALIZATION; ANNULATION; MOLECULE; SCAFFOLD; INDOLES; COMPLEX; ESTERS;
D O I
10.1039/c7ob00059f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diazo compounds play an important role as a coupling partner in the synthesis of unique pi-conjugated 7-azaindole derivatives via rhodium(III)-catalyzed double C-H activation/cyclization.
引用
收藏
页码:2902 / 2905
页数:4
相关论文
共 34 条
[1]  
[Anonymous], 2013, ANGEW CHEM, V125, P10278
[2]   First Approach to Nitrogen-Containing Fused Aromatic Hydrocarbons as Targets for Organoelectronics Utilizing a New Transformation of O-Protected Diaryl Methanols [J].
Balczewski, Piotr ;
Bodzioch, Agnieszka ;
Rozycka-Sokolowska, Ewa ;
Marciniak, Bernard ;
Uznanski, Pawel .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) :2392-2400
[3]   Full Functionalization of the 7-Azaindole Scaffold by Selective Metalation and Sulfoxide/Magnesium Exchange [J].
Barl, Nadja M. ;
Sansiaume-Dagousset, Elodie ;
Karaghiosoff, Konstantin ;
Knochel, Paul .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :10093-10096
[4]   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
[5]   Meriolins (3-(pyrimidin-4-yl)-7-azaindoles): Synthesis, kinase inhibitory activity, cellular effects, and structure of a CDK2/cyclin A/meriolin complex [J].
Echalier, Aude ;
Bettayeb, Karima ;
Ferandin, Yoan ;
Lozach, Olivier ;
Clement, Monique ;
Valette, Annie ;
Liger, Franrcois ;
Marquet, Bernard ;
Morris, Jonathan C. ;
Endicott, Jane A. ;
Joseph, Benoit ;
Meijer, Laurent .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (04) :737-751
[7]   Rh(III)-Catalyzed Cascade Annulation/C-H Attivation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]carbazoles via 1,4-Rhodium Migration [J].
Guo, Songjin ;
Yuan, Kai ;
Gu, Meng ;
Lin, Aijun ;
Yao, Hequan .
ORGANIC LETTERS, 2016, 18 (20) :5236-5239
[8]   A Coupling of Benzamides and Donor/Acceptor Diazo Compounds To Form γ-Lactams via Rh(III)-Catalyzed C-H Activation [J].
Hyster, Todd K. ;
Ruhl, Kyle E. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5364-5367
[9]   Multiple Roles of the Pyrimidyl Group in the Rhodium-Catalyzed Regioselective Synthesis and Functionalization of Indole-3-carboxylic Acid Esters [J].
Jiang, Hui ;
Gao, Shang ;
Xu, Jinyi ;
Wu, Xiaoming ;
Lin, Aijun ;
Yao, Hequan .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) :188-194
[10]   Isolation and synthesis of biologically active carbazole alkaloids [J].
Knölker, HJ ;
Reddy, KR .
CHEMICAL REVIEWS, 2002, 102 (11) :4303-4427