Synthesis of oxindole from acetanilide via Ir(III)-catalyzed C-H carbenoid functionalization

被引：54

作者：

Patel, Pitambar ^{[1
]}

Borah, Gongutri ^{[1
]}

机构：

[1] CSIR North East Inst Sci & Technol, Chem Sci & Technol Div, Jorhat 785006, Assam, India

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 02期

关键词：

METAL-FREE SYNTHESIS; INTRAMOLECULAR ALPHA-ARYLATION; DIAZO-COMPOUNDS; BOND FUNCTIONALIZATION; FACILE SYNTHESIS; N-OXIDES; RH(III)-CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; DIAZOCARBONYL COMPOUNDS; ASYMMETRIC-SYNTHESIS;

D O I：

10.1039/c6cc08788d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we disclose the first report on the synthesis of oxindole derivatives from acetanilide via Ir(III)-catalyzed intermolecular C-H functionalization with diazotized Meldrum's acid. A broad range of substituted anilides were found to react smoothly under the Ir(III)-catalytic system to afford the corresponding N-protected oxindoles. The N-protecting groups, such as Ac, Bz or Piv, can be easily removed to furnish the oxindole. Various synthetic applications of the synthesized oxindole were also demonstrated.

引用

页码：443 / 446

页数：4

共 74 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[2] Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds
Ai, Wen
Yang, Xueyan
Wu, Yunxiang
Wang, Xuan
Li, Yuanchao
Yang, Yaxi
Zhou, Bing
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17653 - 17657
[3] Synthesis of Spiroheterocycles by Palladium-Catalyzed Domino Cycloisomerization/Cross-Coupling of α-Allenols and Baylis-Hillman Acetates
Alcaide, Benito
Almendros, Pedro
Martinez del Campo, Teresa
Teresa Quiros, M.
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (14) : 3344 - 3346
[4] Andreani A, 2000, ANTI-CANCER DRUG DES, V15, P447
[5] Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products
Ashimori, A
Bachand, B
Overman, LE
Poon, DJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) : 6477 - 6487
[6] Strategies for the enantioselective synthesis of spirooxindoles
Ball-Jones, Nicolas R.
Badillo, Joseph J.
Franz, Annaliese K.
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5165 - 5181
[7] REACTION OF INDOLE AND INDOLE GRIGNARD-REAGENT WITH PHOSGENE - FACILE SYNTHESIS OF INDOLE-3-CARBOXYLIC ACID-DERIVATIVES
BERGMAN, J
CARLSSON, R
SJOBERG, B
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (07) : 1123 - 1134
[8] Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates
Chan, Wai-Wing
Lo, Siu-Fung
Zhou, Zhongyuan
Yu, Wing-Yiu
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) : 13565 - 13568
[9] Rh(III)-Catalyzed [4+2] Annulation of Indoles with Diazo Compounds: Access to Pyrimido[1,6-a]indole-1(2H)-ones
Chen, Xun
Hu, Xinwei
Bai, Siyi
Deng, Yuanfu
Jiang, Huanfeng
Zeng, Wei
[J]. ORGANIC LETTERS, 2016, 18 (02) : 192 - 195
[10] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
Chen, Zhengkai
Wang, Binjie
Zhang, Jitan
Yu, Wenlong
Liu, Zhanxiang
Zhang, Yuhong
[J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1107 - 1295

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