Divergent synthesis of 1,3,5-tri and 1,3-disubstituted pyrazoles under transition metal-free conditions

被引：8

作者：

Ma, Liyao ^{[1
,2
]}

Ou, Pengcheng ^{[1
,2
]}

Huang, Xueliang ^{[2
]}

机构：

[1] Fuzhou Univ, Coll Chem, Fuzhou 350116, Peoples R China

[2] Chinese Acad Sci, Univ Chinese Acad Sci, Fujian Coll,Key Lab Coal Ethylene Glycol & Its Re, Ctr Excellence Mol Synth,Fujian Inst Res Struct M, Fuzhou 350002, Fujian, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 33期

关键词：

TOSYLHYDRAZONES VERSATILE REAGENTS; 1,3-DIPOLAR; INSERTION; ACCESS; 5-LIPOXYGENASE; DERIVATIVES; INHIBITION; RIMONABANT; CHEMISTRY;

D O I：

10.1039/d0ob01478h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrazole cores are common structural motifs existing in various agrochemicals and pharmaceuticals. Herein, a transition metal-free, three-component reaction of arylaldehydes, ethyl acrylate andN-tosylhydrazones is described, which leads to the formation of 1,3,5-trisubstituted and 1,3-disubstituted pyrazoles divergently under slightly different conditions.

引用

页码：6487 / 6491

页数：5

共 52 条

[1] The Chemistry of Acetylpyrazoles and Its Utility in Heterocyclic Synthesis [J].

Abdelhamid, Abdou O. ;

Gomha, Sobhi M. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (03) :726-758

[2] A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ [J].

Aggarwal, VK ;

de Vicente, J ;

Bonnert, RV .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5381-5383

[3] Synthesis and fungicidal activity of novel pyrazole derivatives containing 5-Phenyl-2-Furan [J].

Ahmed, Wasim ;

Yan, Xiaojing ;

Hu, Dekun ;

Adnan, Muhammad ;

Tang, Ri-Yuan ;

Cui, Zi-Ning .

BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (19)

[4] Synthesis of Functionalized Pyrazoles via 1,3-Dipolar Cycloaddition of α-Diazo-β-ketophosphonates, Sufones and Esters with Electron-Deficient Alkenes [J].

Baiju, T. V. ;

Namboothiri, Irishi N. N. .

CHEMICAL RECORD, 2017, 17 (10) :939-955

[5] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions [J].

Barluenga, Jose ;

Valdes, Carlos .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) :7486-7500

[6] Recent Developments in the Chemistry of Pyrazoles [J].

Brown, Andrew W. .

ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 126, 2018, 126 :55-107

[7] Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs [J].

Charlier, C ;

Michaux, C .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (7-8) :645-659

[8] Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds [J].

Chen, Gui ;

Song, Jinshuai ;

Yu, Yinghua ;

Luo, Xuesong ;

Li, Chunsen ;

Huang, Xueliang .

CHEMICAL SCIENCE, 2016, 7 (03) :1786-1790

[9] A base-promoted cascade reaction of α,β-unsaturated N-tosylhydrazones with o-hydroxybenzyl alcohols: highly regioselective synthesis of N-sec-alkylpyrazoles [J].

Chen, Lian-Mei ;

Zhao, Juan ;

Xia, An-Jie ;

Guo, Xiao-Qiang ;

Gan, Ya ;

Zhou, Chuang ;

Yang, Zai-Jun ;

Yang, Jun ;

Kang, Tai-Ran .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (37) :8561-8570

[10] Synthesis of celecoxib analogs that possess a N-hydroxypyrid-2(1H)one 5-lipoxygenase pharmacophore: Biological evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity [J].

Chowdhury, Morshed Alam ;

Abdellatif, Khaled R. A. ;

Dong, Ying ;

Das, Dipankar ;

Suresh, Mavanur R. ;

Knaus, Edward E. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (23) :6138-6141

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