Rh(III)-Catalyzed Direct C-H Cyclization of N-Nitrosoanilines with 1,3-Dicarbonyl Compounds: A Route to Tetrahydrocarbazol-4-ones

被引：4

作者：

Jiao, Liulin ^{[1
]}

Zhang, Bo ^{[2
]}

Qu, Bohong ^{[1
]}

Zhai, Ruirui ^{[1
]}

Chen, Xun ^{[1
]}

机构：

[1] Hainan Med Univ, Sch Pharm, Hainan Prov Key Lab Res & Dev Trop Herbs, Key Lab Trop Translat Med,Minist Educ, Haikou 571199, Peoples R China

[2] Jiujiang Univ, Affiliated Hosp, Jiujiang 332000, Jiangxi, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 15期

基金：

海南省自然科学基金; 中国国家自然科学基金;

关键词：

INDOLE SYNTHESIS; BOND FORMATION; ANNULATION; ANILINES;

D O I：

10.1021/acs.joc.3c00714

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and efficient Rh(III)-catalyzed direct C-Hbondtandem annulation of N-nitrosoanilines with 1,3-dicarbonylcompounds through two C-H bond cleavage was developed. Thisprotocol provides a rapid access to a series of valuable tetrahydrocarbazol-4-oneswith the feature of readily available starting materials, broad functionalgroup tolerance, and in situ generation of carbene precursors. Importantly,some reaction products exhibited promising antiproliferative activityin cancer cell lines.

引用

页码：10662 / 10669

页数：8

共 22 条

[1] Synthesis of carbazolones and 3-acetylindoles via oxidative C-N bond formation through PIFA-mediated annulation of 2-aryl enaminones
Ban, Xu
Pan, Yan
Lin, Yingfu
Wang, Songqing
Du, Yunfei
Zhao, Kang
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (18) : 3606 - 3609
[2] Rh(III)-Catalyzed Diverse C-H Functionalization of Iminopyridinium Ylides
Dong, Zhenzhen
Li, Pengfei
Li, Xingwei
Liu, Bingxian
[J]. CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (09) : 2489 - 2494
[3] Rhodium-Catalyzed Directed C(sp2)-H Bond Addition of 2-Arylindazoles to N-Sulfonylformaldimines and Activated Aldehydes
Ghosh, Asim Kumar
Ghosh, Payel
Hajra, Alakananda
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) : 15752 - 15759
[4] Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies
Guimond, Nicolas
Gorelsky, Serge I.
Fagnou, Keith
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) : 6449 - 6457
[5] Recent advances in transition-metal-catalyzed carbene insertion to C-H bonds
He, Yuan
Huang, Zilong
Wu, Kaikai
Ma, Juan
Zhou, Yong-Gui
Yu, Zhengkun
[J]. CHEMICAL SOCIETY REVIEWS, 2022, 51 (07) : 2759 - 2852
[6] An Easy Access to Carbazolones and 2,3-Disubstituted Indoles
Janreddy, Donala
Kavala, Veerababurao
Bosco, J. W. John
Kuo, Chun-Wei
Yao, Ching-Fa
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (12) : 2360 - 2365
[7] Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation
Jiang, Yuqin
Li, Pengfei
Zhao, Jie
Liu, Bingxian
Li, Xingwei
[J]. ORGANIC LETTERS, 2020, 22 (19) : 7475 - 7479
[8] Isolation and synthesis of biologically active carbazole alkaloids
Knölker, HJ
Reddy, KR
[J]. CHEMICAL REVIEWS, 2002, 102 (11) : 4303 - 4427
[9] Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N-Nitrosoanilines and Alkynes
Liang, Yujie
Jiao, Ning
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (12) : 4035 - 4039
[10] Rhodium(III)-Catalyzed Indole Synthesis Using N-N Bond as an Internal Oxidant
Liu, Baoqing
Song, Chao
Sun, Chao
Zhou, Shuguang
Zhu, Jin
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (44) : 16625 - 16631

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