Metal-free synthesis of N-sulfonylformamidines via skeletal reconstruction of sulfonyl oximonitriles

被引：5

作者：

Li, Feng ^{[1
]}

Wu, Ziyan ^{[1
]}

Wang, Jingjing ^{[1
]}

Zhang, Siyuan ^{[1
]}

Yu, Jiaxin ^{[1
]}

Yuan, Zhen ^{[1
]}

Liu, Jingya ^{[1
]}

Shen, Renzeng ^{[1
]}

Zhou, Yao ^{[2
]}

Liu, Lantao ^{[1
,3
]}

机构：

[1] Shangqiu Normal Univ, Coll Chem & Chem Engn, Henan Engn Lab Green Synth Pharmaceut, Shangqiu 476000, Henan, Peoples R China

[2] Hubei Normal Univ, Coll Chem & Chem Engn, Hubei Key Lab Pollutant Anal & Reuse Technol, Huangshi 435002, Hubei, Peoples R China

[3] Zhengzhou Univ, Coll Chem, Zhengzhou 450052, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 03期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; CATALYZED SYNTHESIS; MIGRATION STRATEGY; REARRANGEMENT; AMIDINES; DERIVATIVES; ALKENES; DESIGN; ARYL;

D O I：

10.1039/d1qo01665b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We developed for the first time an unprecedented domino reaction of sulfonyl oximonitriles with secondary amines to streamline the synthesis of N-sulfonylformamidines in decent to high yields under mild reaction conditions. In addition, scale-up experiments and late-stage functionalization of drugs were also performed. Preliminary studies indicate that the loss of a cyano-/benzyloxy-group and a sulfonyl migration process are involved in this reaction.

引用

收藏

页码：627 / 632

页数：6

相关论文

共 65 条

[1] Highly efficient one-pot synthesis of N-sulfonylamidines by Cu-catalyzed three-component coupling of sulfonyl azide, alkyne, and amine [J].

Bae, I ;

Han, H ;

Chang, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (07) :2038-2039

[2] Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents [J].

Bekhit, Adnan A. ;

Ashour, Hayam M. A. ;

Ghany, Yasser S. Abdel ;

Bekhit, Alaa El-Din A. ;

Baraka, Azza .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (03) :456-463

[3] Air-Induced One-Pot Synthesis of N-Sulfonylformamidines from Sulfonyl Chlorides, NaN3, and Tertiary/Secondary Amines [J].

Bi, Wen-Zhu ;

Zhang, Wen-Jie ;

Li, Zi-Jie ;

Xia, Xiao-Yi ;

Chen, Xiao-Lan ;

Qu, Ling-Bo ;

Zhao, Yu-Fen .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (35) :6071-6076

[4] C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].

Brasche, Gordon ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934

[5] Metal- and solvent-free synthesis of N-sulfonylformamidines [J].

Chandna, Nisha ;

Chandak, Navneet ;

Kumar, Pawan ;

Kapoor, Jitander K. ;

Sharma, Pawan K. .

GREEN CHEMISTRY, 2013, 15 (08) :2294-2301

[6] Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of N-Sulfonylamidine Derivatives [J].

Chen, Jijun ;

Long, Wenhao ;

Yang, Yonggang ;

Wan, Xiaobing .

ORGANIC LETTERS, 2018, 20 (09) :2663-2666

[7] Interception of amide ylides with sulfonamides: synthesis of (E)-N-sulfonyl amidines catalyzed by Zn(OTf)2 [J].

Chen, Jijun ;

Long, Wenhao ;

Fang, Shangwen ;

Yang, Yonggang ;

Wan, Xiaobing .

CHEMICAL COMMUNICATIONS, 2017, 53 (99) :13256-13259

[8] Sustainable electrochemical cross-dehydrogenative coupling of 4-quinolones and diorganyl diselenides [J].

Chen, Jin-Yang ;

Wu, Hong-Yu ;

Gui, Qing-Wen ;

Yan, Shan-Shu ;

Deng, Jie ;

Lin, Ying-Wu ;

Cao, Zhong ;

He, Wei-Min .

CHINESE JOURNAL OF CATALYSIS, 2021, 42 (09) :1445-1450

[9] Direct Condensation of Sulfonamide and Formamide: Nal-Catalyzed Synthesis of N-Sulfonyl Formamidine Using TBHP as Oxidant [J].

Chen, Shulin ;

Xu, Yuan ;

Wan, Xiaobing .

ORGANIC LETTERS, 2011, 13 (23) :6152-6155

[10] The Combined C-H Functionalization/Cope Rearrangement: Discovery and Applications in Organic Synthesis [J].

Davies, Huw M. L. ;

Lian, Yajing .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :923-935

← 1 2 3 4 5 6 7 →