Cu(ii)-Mediated aerobic oxidative synthesis of sulfonated chromeno[4,3-c]pyrazol-4(2H)-ones

被引：6

作者：

Zhou, Quan ^{[1
,2
]}

Yu, Hai-Yan ^{[1
,2
]}

Zhou, Yaqing ^{[3
]}

Wei, Jing-Ru ^{[1
,2
]}

Wang, Lei ^{[1
,2
,4
]}

机构：

[1] Taizhou Univ, Adv Res Inst, Taizhou 318000, Zhejiang, Peoples R China

[2] Taizhou Univ, Dept Chem, Taizhou 318000, Zhejiang, Peoples R China

[3] Taizhou Jiaxin Metering & Testing Co Ltd, Dept Chem, Taizhou 317000, Zhejiang, Peoples R China

[4] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2022年 / 20卷 / 28期

基金：

中国国家自然科学基金;

关键词：

SELECTIVE INHIBITORS; DERIVATIVES; CYCLIZATION; DISCOVERY; COUMARIN; CARBONYL; LIGANDS; POTENT;

D O I：

10.1039/d2ob00639a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, starting with propiolates and sulfonyl hydrazides, we developed a concise and facile synthesis of 2-sulfonylated chromeno [4,3-c]pyrazol-4(2H)-ones or 2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-ones via Cu(ii)-promoted oxidative cascade C-C/C-N bond formation. This protocol has the advantages of atom economy and good functional group tolerance. The primary mechanism studies indicate that the reaction involves a free-radical process as well as terminal alkyne C-H activation.

引用

页码：5575 / 5581

页数：7

共 37 条

[1] New 2-arylpyrazolo[4,3-c]quinoline derivatives as potent and selective human A3 adenosine receptor antagonists [J].

Baraldi, PG ;

Tabrizi, MA ;

Preti, D ;

Bovero, A ;

Fruttarolo, F ;

Romagnoli, R ;

Zaid, NA ;

Moorman, AR ;

Varani, K ;

Borea, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) :5001-5008

[2] Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity [J].

Borges, F ;

Roleira, F ;

Milhazes, N ;

Santana, L ;

Uriarte, E .

CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) :887-916

[3] Organocatalytic Electrosynthesis of Cinnolines through Cascade Radical Cyclization and Migration [J].

Cai, Chen ;

Lu, Yi ;

Yuan, Chengcheng ;

Fang, Zheng ;

Yang, Xiaobing ;

Liu, Chengkou ;

Guo, Kai .

ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2021, 9 (50) :16989-16996

[4] Total Syntheses of the Coumarin-Containing Natural Products Pimpinellin and Fraxetin Using Au(I)-Catalyzed Intramolecular Hydroarylation (IMHA) Chemistry [J].

Cervi, Aymeric ;

Aillard, Paul ;

Hazeri, Nourallah ;

Petit, Laurent ;

Chai, Christina L. L. ;

Willis, Anthony C. ;

Banwell, Martin G. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) :9876-9882

[5] A phosphine-catalysed one-pot domino sequence to access cyclopentene-fused coumarins [J].

Chen, Yan-Shan ;

Zheng, Yu ;

Chen, Zhi-Jun ;

Xie, Zhen-Zhen ;

He, Xian-Chen ;

Xiao, Jun-An ;

Chen, Kai ;

Xiang, Hao-Yue ;

Yang, Hua .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (32) :7074-7080

[6] Disposition of fipronil in rats [J].

Cravedi, J. P. ;

Delous, G. ;

Zalko, D. ;

Viguie, C. ;

Debrauwer, L. .

CHEMOSPHERE, 2013, 93 (10) :2276-2283

[7] Cu(OAc)2-Promoted Cascade Carboamination/Oxidative Cyclization of C-Acylimines with Alkenes [J].

Dang, Ling ;

Liang, Libo ;

Qian, Cheng ;

Fu, Meiqin ;

Ma, Tongmei ;

Xu, Dingguo ;

Jiang, Huanfeng ;

Zeng, Wei .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) :769-776

[8] Light-Enabled Radical 1,4-Aryl Migration Via a Phospho-Smiles Rearrangement [J].

De Abreu, Maxime ;

Belmont, Philippe ;

Brachet, Etienne .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05) :3758-3767

[9] Carbonyl and olefin adducts of coinage metals supported by poly(pyrazolyl)borate and poly(pyrazolyl)alkane ligands and silver mediated atom transfer reactions [J].

Dias, H. V. Rasika ;

Lovely, Carl J. .

CHEMICAL REVIEWS, 2008, 108 (08) :3223-3238

[10] Iodine-Catalyzed Double [4+2] Oxidative Annulations for the Synthesis of Bipyrazines from Ketones and Diamines by a Domino Strategy [J].

Ding, Yuxin ;

Zhang, Ruiqin ;

Ma, Renchao ;

Ma, Yongmin .

ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (02) :355-361

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