Rh(III)-Catalyzed Oxidative Annulation of 2-Arylquinoxalines with Cyclic 2-Diazo-1,3-diketones by C-H Bond Activation

被引:3
作者
Ajay, Chidrawar [1 ,3 ]
Chary, Devulapally Yogananda [1 ,3 ]
Balasubramanian, Sridhar [2 ]
Reddy, Basi Subba V. [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Fluoro & Agrochem, Hyderabad 500007, India
[2] CSIR Indian Inst Chem Technol, Lab Xray Crystallog, Hyderabad 500007, India
[3] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, Uttar Pradesh, India
关键词
C-H activation; Cyclic alpha-diazo carbonyl compounds; Transition metal catalysis; 2-Arylquinoxalines; 2; 3-Dihydrodibenzo[a; c]phenazin-4(1H)-ones; AMINATION; DERIVATIVES; AZOBENZENES; ALKYLATION; CATALYSIS; KETONES; ALKYNES;
D O I
10.1002/ejoc.202201361
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rh(III)-catalyzed C -H bond annulation of 2-arylquinoxalines with cyclic 2-diazo-1,3-diketones has been accomplished for the first time to synthesize a novel series of 2,3dihydrodibenzo[a,c]phenazin-4(1H)-one frameworks by means of carbene insertion followed by condensation. The reaction proceeds through the C -H bond activation and functionalization of 2-arylquinoxalines using Rh(III)/AgSbF6 complex to produce highly substituted 2,3-dihydrodibenzo[a,c]phenazin4(1H)-one and benzo[5,6][1,2,4]thiadiazino[2,3-f]phenanthridin5(6H)-one-10,10-dioxide derivatives in good to excellent yields.
引用
收藏
页数:8
相关论文
共 50 条
[41]   Rh(III)-Catalyzed Redox-Neutral C-H Activation/[3+2] Annulation of N-Phenoxy Amides with Propargylic Monofluoroalkynes [J].
Zhong, Xiuhua ;
Lin, Shuang ;
Gao, Hui ;
Liu, Fu-Xiaomin ;
Zhou, Zhi ;
Yi, Wei .
ORGANIC LETTERS, 2021, 23 (06) :2285-2291
[42]   Rh(III)-Catalyzed Synthesis of 2-Nitro-2H -azirines via sp3 C-H Activation [J].
Huang, Xiaojun ;
Ge, Yun ;
Qian, Yang ;
Zhang, Zhengyu .
SYNLETT, 2022, 33 (10) :969-972
[43]   Quinoxaline as an integrated directing group in palladium-catalyzed ortho-C-H bond arylation of the aryl unit of 2-arylquinoxalines [J].
Idris, Imane ;
Derridj, Fazia ;
Roisnel, Thierry ;
Doucet, Henri ;
Soule, Jean-Francois .
NEW JOURNAL OF CHEMISTRY, 2018, 42 (19) :16036-16039
[44]   Rh(III)-Catalyzed C-H Activation/Annulation of N-Methyl Arylhydrazines with Iodonium Ylides toward Ring-fused Cinnolines [J].
Pan, Changduo ;
Yuan, Cheng ;
Chen, Dongdong ;
Chen, Yuefeng ;
Yu, Jin-Tao .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (02)
[45]   The regioselective synthesis of 2-phosphinoylindoles via Rh(III)-catalyzed C-H activation [J].
Wang, Huanan ;
Li, Shuaiqi ;
Wang, Baiquan ;
Li, Bin .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (01) :88-91
[46]   Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C-H/C-C bond activation [J].
Cui, Yixin ;
Bai, Dachang ;
Liu, Bingxian ;
Chang, Junbiao ;
Li, Xingwei .
CHEMICAL COMMUNICATIONS, 2020, 56 (100) :15631-15634
[47]   Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation [J].
Zhang, Yan-Bo ;
Li, Bin-Shi ;
Xu, Guo-Jie ;
Sun, Wei ;
Sun, Meng .
ORGANIC LETTERS, 2023, 25 (21) :3922-3926
[48]   Ru(II)- or Rh(III)-Catalyzed Annulation of Aromatic/Vinylic Acids withAlkylidenecyclopropanes via C-H Activation [J].
Ramesh, Balu ;
Jeganmohan, Masilamani .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) :5668-5681
[49]   One-Pot Construction of Indolo[2,3-b]quinoxalines through Ruthenium-Catalyzed Ortho C-H Bond Functionalization of 2-Arylquinoxalines with Sulfonyl Azides [J].
Laru, Sudip ;
Bhattacharjee, Suvam ;
Ghosh, Sumit ;
Hajra, Alakananda .
ORGANIC LETTERS, 2021, 23 (19) :7624-7629
[50]   One-Pot Rh(III)-Catalyzed Twofold C-H Activation/Oxidative Annulation of N-Arylpyrroles with Alkynes to Fluorescent Ullazines [J].
Otero-Riesgo, Sergio ;
Varela, Jesus A. ;
Saa, Carlos .
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) :2312-2323