Ir(III)-catalyzed synthesis of isoquinolines from benzimidates and α-diazocarbonyl compounds

被引:30
作者
Yang, Xiaobo [1 ]
Jie, Jiyang [1 ]
Li, Haoyi [1 ]
Piao, Meihui [1 ]
机构
[1] Shenyang Normal Univ, Inst Catalysis Energy & Environm, Coll Chem & Chem Engn, Shenyang 110034, Liaoning, Peoples R China
基金
中国国家自然科学基金;
关键词
PALLADIUM-CATALYZED IMINOANNULATION; ASYMMETRIC-SYNTHESIS; AROMATIC KETIMINES; INTERNAL ALKYNES; DIAZO-COMPOUNDS; N-OXIDES; CYCLIZATION; ACTIVATION; ANNULATION; PYRIDINES;
D O I
10.1039/c6ra10045g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein a tandem Ir(III)-catalyzed C-H activation and annulation reaction for the synthesis of isoquinolines by using readily available substituted benzimidates and alpha-diazocarbonyl compounds under mild conditions. The catalytic reaction exhibits excellent tolerance to different functional groups and the corresponding isoquinolines were obtained in good to excellent yields. This novel method affords an alternative strategy for the construction of diverse and useful isoquinoline derivatives.
引用
收藏
页码:S7371 / S7374
页数:4
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[1]   β-Phenylethylamines and the isoquinoline alkaloids [J].
Bentley, KW .
NATURAL PRODUCT REPORTS, 2005, 22 (02) :249-268
[2]   Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization [J].
Boudou, M ;
Enders, D .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9486-9494
[3]   Rh(III)-catalyzed C-H alkylation of 2-arylbenzothiazoles with α-diazo esters [J].
Choi, Miji ;
Park, Jihye ;
Mishra, Neeraj Kumar ;
Lee, Seok-Yong ;
Kim, Jun Hyeong ;
Jeong, Kyung Mm ;
Lee, Jeongmi ;
Jung, Young Hoon ;
Kim, In Su .
TETRAHEDRON LETTERS, 2015, 56 (32) :4678-4682
[4]   Asymmetric synthesis of isoquinoline alkaloids [J].
Chrzanowska, M ;
Rozwadowska, MD .
CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370
[5]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[6]   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
[7]   Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines [J].
Dai, GX ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7042-7047
[8]   Synthesis of 3,4-disubstituted isoquinolines via palladium-catalyzed cross-coupling of o-(1-alkynyl)benzaldimines and organic halides [J].
Dai, GX ;
Larock, RC .
ORGANIC LETTERS, 2001, 3 (25) :4035-4038
[9]   Privileged structures: Applications in drug discovery [J].
DeSimone, RW ;
Currie, KS ;
Mitchell, SA ;
Darrow, JW ;
Pippin, DA .
COMBINATORIAL CHEMISTRY & HIGH THROUGHPUT SCREENING, 2004, 7 (05) :473-493
[10]  
GENSLER WJ, 1951, ORG REACTIONS, V6, P191