Synthesis of Isoquinoline from Benzimidates via Ru(II)-Catalyzed C-H Alkylation/Annulations with Diazo Compounds

被引:12
作者
Borah, Gongutri [1 ]
Ramaiah, Danaboyina [1 ]
Patel, Pitambar [1 ]
机构
[1] CSIR, Chem Sci & Technol Div, North East Inst Sci & Technol, Jorhat 785006, Assam, India
关键词
C-H annulation; benzimidate; diazo compounds; isoquinoline; ruthenium catalysis; ALPHA-DIAZOCARBONYL COMPOUNDS; BISCHLER-NAPIERALSKI REACTION; CARBENE MIGRATORY INSERTION; BETA-PHENYLETHYLAMINES; ASYMMETRIC-SYNTHESIS; CARBONYL-COMPOUNDS; DIRECTING GROUPS; BOND ACTIVATION; FUNCTIONALIZATION; ANNULATION;
D O I
10.1002/slct.201802831
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Ru(II)-catalyzed C-H alkylation/annulations of benzimidate with diazo compounds have been developed for the synthesis of functionalized isoquinoline. The reaction proceeds under mild condition and exhibit broad functional group tolerance. This strategy also provides a direct approach to isoquinolines and 3,4-dihydrophenanthridin synthesis. Moreover, Ru(II)-catalyzed C-H carbenoid functionalization of benzimidate with diazodiester is also demonstrated.
引用
收藏
页码:10333 / 10337
页数:5
相关论文
共 69 条
[11]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[12]   Rh(III)-Catalyzed [4+2] Annulation of Indoles with Diazo Compounds: Access to Pyrimido[1,6-a]indole-1(2H)-ones [J].
Chen, Xun ;
Hu, Xinwei ;
Bai, Siyi ;
Deng, Yuanfu ;
Jiang, Huanfeng ;
Zeng, Wei .
ORGANIC LETTERS, 2016, 18 (02) :192-195
[13]   Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].
Chen, Zhengkai ;
Wang, Binjie ;
Zhang, Jitan ;
Yu, Wenlong ;
Liu, Zhanxiang ;
Zhang, Yuhong .
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295
[14]   Ruthenium-catalyzed stereoselective intramolecular carbenoid C-H insertion for β- and γ-lactam formations by decomposition of α-diazoacetamides [J].
Choi, MKW ;
Yu, WY ;
Che, CM .
ORGANIC LETTERS, 2005, 7 (06) :1081-1084
[15]   Asymmetric synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Rozwadowska, MD .
CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370
[16]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[17]   Diphenyl quinolines and isoquinolines: Synthesis and primary biological evaluation [J].
Croisy-Delcey, M ;
Croisy, A ;
Carrez, D ;
Huel, C ;
Chiaroni, A ;
Ducrot, P ;
Bisagni, E ;
Jin, L ;
Leclercq, G .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (11) :2629-2641
[18]   Weakly Coordinating Directing Groups for Ruthenium(II)-Catalyzed C-H Activation [J].
De Sarkar, Suman ;
Liu, Weiping ;
Kozhushkov, Sergei I. ;
Ackermann, Lutz .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (07) :1461-1479
[19]   Rh(III)-Catalyzed C-H Activation of Benzoylacetonitriles and Tandem Cyclization with Diazo Compounds to Substituted Benzo[de]chromenes [J].
Fang, Feifei ;
Zhang, Chunmei ;
Zhou, Chaofan ;
Li, Yazhou ;
Zhou, Yu ;
Liu, Hong .
ORGANIC LETTERS, 2018, 20 (07) :1720-1724
[20]   Modern Organic Synthesis with α-Diazocarbonyl Compounds [J].
Ford, Alan ;
Miel, Hugues ;
Ring, Aoife ;
Slattery, Catherine N. ;
Maguire, Anita R. ;
McKervey, M. Anthony .
CHEMICAL REVIEWS, 2015, 115 (18) :9981-10080