Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones

被引：17

作者：

Yu, Xinzhang ^{[1
]}

Shang, Yu-Zhu ^{[2
]}

Cheng, Yu-Fei ^{[2
]}

Tian, Jun ^{[2
]}

Niu, Yulan ^{[1
]}

Gao, Wen-Chao ^{[2
]}

机构：

[1] Taiyuan Inst Nchnol, Dept Chem & Chem Engn, Taiyuan 030008, Peoples R China

[2] Taiyuan Univ Technol, Coll Biomed Engn, Taiyuan 030024, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 09期

关键词：

N-SULFANYLSUCCINIMIDES; NEXT-GENERATION; SULFUR; CYCLIZATION;

D O I：

10.1039/d0ob00050g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile method for the synthesis of 4-chalcogenylated pyrazoles has been developed via electrophilic chalcogenation/cyclization of alpha,beta-alkynic hydrazones. The cyclization of alpha,beta-alkynic aldehyde hydrazones could be induced by using either sulfenyl chloride or the S-electrophiles generated in situ from the reaction of NCS and arythiol. The developed method was successfully applied to the synthesis of the sulfenyl analogue of celecoxib.

引用

页码：1806 / 1811

页数：6

共 38 条

[1]

[Anonymous], 2018, SULFUR CHEM

[2] Review: biologically active pyrazole derivatives [J].

Ansari, Anam ;

Ali, Abad ;

Asif, Mohd ;

Shamsuzzaman .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) :16-41

[3] A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design [J].

Beno, Brett R. ;

Yeung, Kap-Sun ;

Bartberger, Michael D. ;

Pennington, Lewis D. ;

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (11) :4383-4438

[4] Synthesis of Aryl Thioethers through the N-Chlorosuccinimide-Promoted Cross-Coupling Reaction of Thiols with Grignard Reagents [J].

Cheng, Jun-Hao ;

Ramesh, Chintakunta ;

Kao, Hsin-Lun ;

Wang, Yu-Jen ;

Chan, Chien-Ching ;

Lee, Chin-Fa .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :10369-10374

[5] Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry [J].

Feng, Minghao ;

Tang, Bingqing ;

Liang, Steven H. ;

Jiang, Xuefeng .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) :1200-1216

[6] N-Alkynylthio Phthalimide: A Shelf-Stable Alkynylthio Transfer Reagent for the Synthesis of Alkynyl Thioethers [J].

Gao, Wen-Chao ;

Shang, Yu-Zhu ;

Chang, Hong-Hong ;

Li, Xing ;

Wei, Wen-Long ;

Yu, Xin-Zhang ;

Zhou, Rong .

ORGANIC LETTERS, 2019, 21 (15) :6021-6024

[7] Synthesis of 4-Sulfenyl Isoxazoles through AlCl3-Mediated Electrophilic Cyclization and Sulfenylation of 2-Alkyn-1-one O-Methyloximes [J].

Gao, Wen-Chao ;

Cheng, Yu-Fei ;

Chang, Hong-Hong ;

Li, Xing ;

Wei, Wen-Long ;

Yang, Peng .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07) :4312-4317

[8] AlCl3-Catalyzed Intramolecular Cyclization of N-Arylpropynamides with N-Sulfanylsuccinimides: Divergent Synthesis of 3-Sulfenyl Quinolin-2-ones and Azaspiro[4,5]trienones [J].

Gao, Wen-Chao ;

Liu, Tao ;

Cheng, Yu-Fei ;

Chang, Hong-Hong ;

Li, Xing ;

Zhou, Rong ;

Wei, Wen-Long ;

Qiao, Yan .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24) :13459-13467

[9] Synthesis of 3-Sulfenylated Coumarins: BF3•Et2O-Mediated Electrophilic Cyclization of Aryl Alkynoates Using N-Sulfanylsuccinimides [J].

Gao, Wen-Chao ;

Liu, Tao ;

Zhang, Bing ;

Li, Xing ;

Wei, Wen-Long ;

Liu, Qiang ;

Tian, Jun ;

Chang, Hong-Hong .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22) :11297-11304

[10] Transition-Metal-Free Thioamination of Arynes Using Sulfenamides [J].

Gaykar, Rahul N. ;

Bhattacharjee, Subrata ;

Biju, Akkattu T. .

ORGANIC LETTERS, 2019, 21 (03) :737-740

← 1 2 3 4 →