Highly selective and efficient synthesis of 3-arylamino-substituted 5-aminopyrazole-4-carboxylates under microwave irradiation

被引：10

作者：

Lim, Felicia Phei Lin ^{[1
]}

Gan, Rowena Xin Yi ^{[1
]}

Dolzhenko, Anton V. ^{[1
,2
]}

机构：

[1] Monash Univ Malaysia, Sch Pharm, Jalan Lagoon Selatan, Bandar Sunway 47500, Selangor Darul, Malaysia

[2] Curtin Univ, Curtin Hlth Innovat Res Inst, Sch Pharm, Fac Hlth Sci, GPO Box U1987, Perth, WA 6845, Australia

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 08期

关键词：

Microwave-assisted synthesis; Selectivity; Pyrazole; Hydrazine; 3-AMINOPYRAZOLE INHIBITORS; ONE-POT; ASSISTED SYNTHESIS; CRYSTAL-STRUCTURE; KINASE INHIBITOR; ANTITUMOR AGENTS; DERIVATIVES; SAR; 2-CYANOACRYLATES; IDENTIFICATION;

D O I：

10.1016/j.tetlet.2017.01.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved microwave-assisted method was developed for the preparation of ethyl 5-aminopyrazole carboxylates from ethyl 2-cyano-3-methylthioacrylates and hydrazine. It was shown that using microwave irradiation significantly reduced the reaction time and improved the process selectivity and yield. The reaction proved to be reproducible in different microwave reactors and on large scale, affording the desired products in high yields and purity. A representative library of 3-arylamino-substituted 5aminopyrazole-4-carboxylates was successfully prepared to assess the scope of the method. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：775 / 778

页数：4

共 31 条

[1] SYNTHESIS OF SOME NOVEL α-CYANOKETENE-N, S-ACETALS DERIVED FROM SECONDARY ALIPHATIC AMINES AND THEIR USE IN PYRAZOLE SYNTHESIS [J].

Al-Adiwish, Wedad M. ;

Tahir, M. I. M. ;

Yaacob, W. A. .

SYNTHETIC COMMUNICATIONS, 2013, 43 (23) :3203-3216

[2]

De La Hoz A, 2004, CURR ORG CHEM, V8, P903

[3] Novel cyanoketene N,S-acetals and pyrazole derivatives using potassium 2-cyanoethylene-1-thiolates [J].

Elgemeie, Galal H. ;

Elghandour, Ahmed H. ;

Elaziz, Ghada W. Abd .

SYNTHETIC COMMUNICATIONS, 2007, 37 (17) :2827-2834

[4] Microwave-assisted synthesis of N-heterocycles in medicinal chemistry [J].

Garella, Davide ;

Borretto, Emily ;

Di Stilo, Antonella ;

Martina, Katia ;

Cravotto, Giancarlo ;

Cintas, Pedro .

MEDCHEMCOMM, 2013, 4 (10) :1323-1343

[5] Regioselective Synthesis of 7-(Trimethylsilylethynyl)pyrazolo[1,5-a]pyrimidines via Reaction of Pyrazolamines with Enynones [J].

Golubev, Pavel ;

Karpova, Ekaterina A. ;

Pankova, Alena S. ;

Sorokina, Mariia ;

Kuznetsov, Mikhail A. .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22) :11268-11275

[6]

Hassan Ashraf S, 2015, Sci Pharm, V83, P27, DOI 10.3797/scipharm.1409-14

[7] 5-Aminopyrazole-4-carboxamide analogues are selective inhibitors of Plasmodium falciparum microgametocyte exflagellation and potential malaria transmission blocking agents [J].

Huang, Wenlin ;

Hulverson, Matthew A. ;

Zhang, Zhongsheng ;

Choi, Ryan ;

Hart, Kevin J. ;

Kennedy, Mark ;

Vidadala, Rama Subba Rao ;

Maly, Dustin J. ;

Van Voorhis, Wesley C. ;

Lindner, Scott E. ;

Fan, Erkang ;

Ojo, Kayode K. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (22) :5487-5491

[8] SAR Studies of 5-Aminopyrazole-4-carboxamide Analogues as Potent and Selective Inhibitors of Toxoplasma gondii CDPK1 [J].

Huang, Wenlin ;

Ojo, Kayode K. ;

Zhang, Zhongsheng ;

Rivas, Kasey ;

Vidadala, Rama Subba Rao ;

Scheele, Suzanne ;

DeRocher, Amy E. ;

Choi, Ryan ;

Hulverson, Matthew A. ;

Barrett, Lynn K. ;

Bruzual, Igor ;

Siddaramaiah, Latha Kallur ;

Kerchner, Keshia M. ;

Kurnick, Matthew D. ;

Freiberg, Gail M. ;

Kempf, Dale ;

Hol, Wim G. J. ;

Merritt, Ethan A. ;

Neckermann, Georg ;

de Hostos, Eugenio L. ;

Isoherranen, Nina ;

Maly, Dustin J. ;

Parsons, Marilyn ;

Doggett, J. Stone ;

Van Voorhis, Wesley C. ;

Fang, Erkang .

ACS MEDICINAL CHEMISTRY LETTERS, 2015, 6 (12) :1184-1189

[9] Highly diastereoselective synthesis of quinoline-2,5-diones and pyrazolo[3,4-b]pyridin-6(7H)-ones under microwave irradiation [J].

Jiang, Bo ;

Liang, Yan-Bo ;

Kong, Li-Fang ;

Tu, Xing-Jun ;

Hao, Wen-Juan ;

Ye, Qin ;

Tu, Shu-Jiang .

RSC ADVANCES, 2014, 4 (97) :54480-54486

[10] Arylazopyrazole AAP1742 Inhibits CDKs and Induces Apoptosis in Multiple Myeloma Cells via Mcl-1 Downregulation [J].

Jorda, Radek ;

Navratilova, Jana ;

Huskova, Zlata ;

Schuetznerova, Eva ;

Cankar, Petr ;

Strnad, Miroslav ;

Krystof, Vladimir .

CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 84 (04) :402-408

← 1 2 3 4 →