Rhodium(III)-Catalyzed Cascade C-H Activation/Annulation of N-carbamoylindoles with Silyl Enol Ethers for the Construction of Dihydropyrimidoindolone Skeletons

被引:3
作者
Chen, Lu [1 ]
Wang, Zhichao [1 ]
Pang, Binghan [1 ]
Wang, Yangyang [1 ]
Xu, Xiaobo [1 ]
Wu, Gaorong [1 ]
Ji, Yafei [1 ]
机构
[1] East China Univ Sci & Technol, Sch Pharm, Minist Educ, Engn Res Ctr Pharmaceut Proc Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H activation; cascade annulation reaction; silyl enol ethers; N-carbamoylindoles; rhodium; NITROGEN-CONTAINING HETEROCYCLES; ONE-POT; ALPHA-ARYLATION; INDOLES; ANNULATION; ACTIVATION/CYCLIZATION; CYCLOMETALATION; ALKENYLATION; DERIVATIVES; CYCLIZATION;
D O I
10.1002/ajoc.202100415
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel route to 3,4-dihydropyrimido[1,6-a]indol-1(2H)-one derivatives enabled by Rh(III)-catalyzed cascade C-H activation/annulation of N-carbamoylindoles with silyl enol ethers has been reported. The reaction features mild conditions, wide substrate scope, diverse functional group tolerance and moderate to good yields. Furthermore, a plausible reaction mechanism is confirmed by an available rhodacycle intermediate.
引用
收藏
页码:2603 / 2610
页数:8
相关论文
共 63 条
[1]  
[Anonymous], 2013, ANGEW CHEM, V125, P11942
[2]  
[Anonymous], 2016, ANGEW CHEM, V128, P10734
[3]  
[Anonymous], 2012, Angew. Chem, V124, P3120
[4]  
Bandini M., 2009, ANGEW CHEM, V121, P9786
[5]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[6]   Copper-Catalyzed Multicomponent Coupling of Organoindium Reagents with Nitrogen-Containing Aromatic Heterocycles [J].
Beveridge, Ramsay E. ;
Black, Daniel A. ;
Arndtsen, Bruce A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (19) :3650-3656
[7]   A Flexible, Convergent Approach to Polycyclic Indole Structures: Formal Synthesis of (±)-Mersicarpine [J].
Biechy, Aurelien ;
Zard, Samir Z. .
ORGANIC LETTERS, 2009, 11 (13) :2800-2803
[8]   One-pot sequential Cu-catalyzed reduction and Pd-catalyzed arylation of silyl enol ethers [J].
Chae, JH ;
Yun, JS ;
Buchwald, SL .
ORGANIC LETTERS, 2004, 6 (26) :4809-4812
[9]   Selective Synthesis of Fused Tricyclic [1,3]oxazino[3,4-a]indolone and Dihydropyrimido [1,6-a]indolone via Rh(III)-catalyzed [3+3] or [4+2] C-H Annulation [J].
Chen, Junyu ;
Zhong, Tianshuo ;
Zheng, Xiangyun ;
Yin, Chuanliu ;
Zhang, Lei ;
Zhou, Jian ;
Jiang, Xinpeng ;
Yu, Chuanming .
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) :446-452
[10]   Rh(III)-Catalyzed C-H Activation/Cyclization of Benzamides and Diazonaphthalen-2(1H)-ones for Synthesis of Lactones [J].
Chen, Renjie ;
Cui, Sunliang .
ORGANIC LETTERS, 2017, 19 (15) :4002-4005