A Rh(III)-Catalyzed Cascade C-H Functionalization/C(sp3)-C(sp3) Formation/Cyclization Reaction for the Synthesis of Isoquinolinedione Derivatives

被引:3
作者
Bai, Peng [1 ]
Huang, Kenneth L. [2 ]
Huang, Zhi-Zhen [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
[2] Lakeside High Sch, 533 Blue Ridge Dr, Augusta, GA 30809 USA
来源
SYNTHESIS-STUTTGART | 2017年 / 49卷 / 24期
基金
中国国家自然科学基金;
关键词
cascade; C-H functionalization; C(sp(3))-C(sp(3)) bond; rhodium(III) catalysis; synthesis; ALPHA-DIAZOCARBONYL COMPOUNDS; INTERMOLECULAR CARBENOID FUNCTIONALIZATION; DIAZO-COMPOUNDS; N BOND; ORGANIC-SYNTHESIS; METAL CARBENE; ACTIVATION; INSERTION; BENZAMIDES; C(SP(3))-H;
D O I
10.1055/s-0036-1588566
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cascade C-H functionalization/C(sp(3))-C(sp(3)) formation/cyclization reaction of N-methoxybenzamides with diazomalonates under rhodium(III) catalysis is developed for the efficient synthesis of isoquinolinedione derivatives. A plausible mechanism involving double migratory insertions of carbenes for the formation of C(sp(2))-C(sp(3)) and C(sp(3))-C(sp(3)) bonds by rhodium(III) catalysis is also proposed.
引用
收藏
页码:5357 / 5363
页数:7
相关论文
共 39 条
[1]   Cascade C-H Functionalization/Amidation Reaction for Synthesis of Azepinone Derivatives [J].
Bai, Peng ;
Huang, Xing-Fen ;
Xu, Guo-Dong ;
Huang, Zhi-Zhen .
ORGANIC LETTERS, 2016, 18 (13) :3058-3061
[2]   Magnesium Chelating 2-Hydroxyisoquinoline-1,3(2H,4H)-diones, as Inhibitors of HIV-1 Integrase and/or the HIV-1 Reverse Transcriptase Ribonuclease H Domain: Discovery of a Novel Selective Inhibitor of the Ribonuclease H Function [J].
Billamboz, Muriel ;
Bailly, Fabrice ;
Lion, Cedric ;
Touati, Nadia ;
Vezin, Herve ;
Calmels, Christina ;
Andreola, Marie-Line ;
Christ, Frauke ;
Debyser, Zeger ;
Cotelle, Philippe .
JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (06) :1812-1824
[3]   Catalytic functionalization of low reactive C(sp3)-H and C(sp2)-H bonds of alkanes and arenes by carbene transfer from diazo compounds [J].
Caballero, Ana ;
Diaz-Requejo, M. Mar ;
Fructos, Manuel R. ;
Olmos, Andrea ;
Urbano, Juan ;
Perez, Pedro J. .
DALTON TRANSACTIONS, 2015, 44 (47) :20295-20307
[4]   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
[5]   Rh(III)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3-H bonds [J].
Chen, Xun ;
Xie, Ying ;
Xiao, Xinsheng ;
Li, Guoqiang ;
Deng, Yuanfu ;
Jiang, Huanfeng ;
Zeng, Wei .
CHEMICAL COMMUNICATIONS, 2015, 51 (83) :15328-15331
[6]   Regioselective Syntheses of 1,2-Benzothiazines by Rhodium-Catalyzed Annulation Reactions [J].
Cheng, Ying ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (42) :12349-12352
[7]   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
[8]   Rh(III)-Catalyzed C-H Cyclization of Arylnitrones with Diazo Compounds: Access to N-Hydroxyindolines [J].
Dateer, Ramesh B. ;
Chang, Sukbok .
ORGANIC LETTERS, 2016, 18 (01) :68-71
[9]   Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].
Davies, HML ;
Beckwith, REJ .
CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903
[10]   Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].
Davies, Huw M. L. ;
Manning, James R. .
NATURE, 2008, 451 (7177) :417-424