Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes

被引:5
作者
Chen, Shao-Yong [1 ,2 ,3 ]
Zheng, Yi-Chuan [3 ]
Liu, Xu-Ge [4 ]
Song, Jia-Lin [3 ]
Shu, Bing [3 ]
Zheng, Tao [3 ]
Xiao, Lin [3 ]
Zhang, Shang-Shi [3 ]
Cao, Hua [1 ,2 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Zhongshan 528458, Peoples R China
[2] Guangdong Pharmaceut Univ, Guangdong Cosmet Engn & Technol Res Ctr, Zhongshan 528458, Peoples R China
[3] Guangdong Pharmaceut Univ, Ctr Drug Res & Dev, Guangzhou 510006, Peoples R China
[4] Henan Univ, Sch Pharm, Kaifeng 475004, Henan, Peoples R China
关键词
Indazolones; Rh(III)-Catalyzed; C-H activation; Amidation; ACTIVATION; FUNCTIONALIZATION; DERIVATIVES; CINNOLINES; RECEPTOR;
D O I
10.1002/adsc.202200570
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The Cp*Rh(III)-catalyzed indazolone-directed C-H bond amidation of arenes has been realized by employing sulfonyl azide agents and dioxazolones as nitrogen source. This protocol displays mild conditions, broad substrate scope and high functional group compatibility. What' more, the late-stage modifications of structure complicated drugs, such as Gemfibrozil, Oxaprozin, Probenecid and Naproxen, has been demonstrated. Furthermore, preliminary mechanistic investigation and an exploratory reaction mechanism were also proposed.
引用
收藏
页码:3302 / 3309
页数:8
相关论文
共 47 条
[1]   Synthesis and antiinflammatory activity of novel indazolones [J].
Abouzid, KAM ;
El-Abhar, HS .
ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (01) :1-8
[2]   O-Directed C-H functionalization via cobaltacycles: a sustainable approach for C-C and C-heteroatom bond formations [J].
Banjare, Shyam Kumar ;
Nanda, Tanmayee ;
Pati, Bedadyuti Vedvyas ;
Biswal, Pragati ;
Ravikumar, Ponneri Chandrababu .
CHEMICAL COMMUNICATIONS, 2021, 57 (30) :3630-3647
[3]   Indazole derivatives as novel bradykinin B1 receptor antagonists [J].
Bodmer-Narkevitch, Vera ;
Anthony, Neville J. ;
Cofre, Victoria ;
Jolly, Samson M. ;
Murphy, Kathy L. ;
Ransom, Richard W. ;
Reiss, Duane R. ;
Tang, Cuyue ;
Prueksaritanont, Thomayant ;
Pettibone, Douglas J. ;
Bock, Mark G. ;
Kuduk, Scott D. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :7011-7014
[4]   The recent impact of solid-phase synthesis on medicinally relevant benzoannelated nitrogen heterocycles [J].
Bräse, S ;
Gil, C ;
Knepper, K .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (08) :2415-2437
[5]   INDAZOLINONES, A NEW SERIES OF REDOX-ACTIVE 5-LIPOXYGENASE INHIBITORS WITH BUILT-IN SELECTIVITY AND ORAL ACTIVITY [J].
BRUNEAU, P ;
DELVARE, C ;
EDWARDS, MP ;
MCMILLAN, RM .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :1028-1036
[6]   Substituted Indazoles as Nav1.7 Blockers for the Treatment of Pain [J].
Frost, Jennifer M. ;
DeGoey, David A. ;
Shi, Lei ;
Gum, Rebecca J. ;
Fricano, Meagan M. ;
Lundgaard, Greta L. ;
El-Kouhen, Odile F. ;
Hsieh, Gin C. ;
Neelands, Torben ;
Matulenko, Mark A. ;
Daanen, Jerome F. ;
Pai, Madhavi ;
Ghoreishi-Haack, Nayereh ;
Zhan, Cenchen ;
Zhang, Xu-Feng ;
Kort, Michael E. .
JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (07) :3373-3391
[7]   Synthesis of indazole motifs and their medicinal importance: An overview [J].
Gaikwad, Digambar D. ;
Chapolikar, Archana D. ;
Devkate, Chandrashekhar G. ;
Warad, Khandu D. ;
Tayade, Amit P. ;
Pawar, Rajendra P. ;
Domb, Abraham J. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 :707-731
[8]   Mild metal-catalyzed C-H activation: examples and concepts [J].
Gensch, T. ;
Hopkinson, M. N. ;
Glorius, F. ;
Wencel-Delord, J. .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) :2900-2936
[9]   Synthesis of quaternary carbon-centered indolo[1,2-a]quinazolinones and indazolo[1,2-a]indazolones via C-H functionalization [J].
Gogoi, Kongkona ;
Bora, Bidisha R. ;
Borah, Geetika ;
Sarma, Bipul ;
Gogoi, Sanjib .
CHEMICAL COMMUNICATIONS, 2021, 57 (11) :1388-1391
[10]   Palladium-Catalyzed Transformations of Alkyl C-H Bonds [J].
He, Jian ;
Wasa, Masayuki ;
Chan, Kelvin S. L. ;
Shao, Ojan ;
Yu, Jin-Quan .
CHEMICAL REVIEWS, 2017, 117 (13) :8754-8786