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
[1]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[2]   Cp*Ir(iii)-catalyzed C-H/N-H functionalization of sulfoximines for the synthesis of 1,2-benzothiazines at room temperature [J].
Aher, Yogesh N. ;
Lade, Dhanaji M. ;
Pawar, Amit B. .
CHEMICAL COMMUNICATIONS, 2018, 54 (49) :6288-6291
[3]   SYNTHESIS AND RESOLUTION OF 1-(2-DIPHENYLPHOSPHINO-1-NAPHTHYL)ISOQUINOLINE - A P-N CHELATING LIGAND FOR ASYMMETRIC CATALYSIS [J].
ALCOCK, NW ;
BROWN, JM ;
HULMES, DI .
TETRAHEDRON-ASYMMETRY, 1993, 4 (04) :743-756
[4]  
[Anonymous], 2012, ANGEW CHEM, V124, P10382
[5]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[6]   An Ir(III)-catalyzed aryl C-H bond carbenoid functionalization cascade: access to 1,3-dihydroindol-2-ones [J].
Bai, Siyi ;
Chen, Xun ;
Hu, Xinwei ;
Deng, Yuanfu ;
Jiang, Huanfeng ;
Zeng, Wei .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) :3638-3647
[7]   β-Phenylethylamines and the isoquinoline alkaloids [J].
Bentley, Kenneth W. .
NATURAL PRODUCT REPORTS, 2006, 23 (03) :444-463
[8]   β-Phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 2005, 22 (02) :249-268
[9]   Rhodium(III)-Catalyzed Regioselective Direct C4-Alkylation and C2-Annulation of Indoles: Straightforward Access to Indolopyridone [J].
Biswas, Aniruddha ;
Samanta, Rajarshi .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (12) :1426-1436
[10]   Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization [J].
Boudou, M ;
Enders, D .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9486-9494