A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I

被引：5

作者：

Yang, Shang-Feng ^{[1
]}

Li, Pei ^{[1
]}

Fang, Zi-Lin ^{[1
]}

Liang, Sen ^{[1
]}

Tian, Hong-Yu ^{[1
]}

Sun, Bao-Guo ^{[1
]}

Xu, Kun ^{[2
]}

Zeng, Cheng-Chu ^{[2
]}

机构：

[1] Beijing Technol & Business Univ, Beijing Adv Innovat Ctr Food Nutr & Human Hlth, Beijing Key Lab Flavor Chem, Beijing 100048, Peoples R China

[2] Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 18卷

基金：

中国国家自然科学基金;

关键词：

2-aminothiazoles; electrosynthesis; indirect electrolysis; halide ion; SOLID ACID; DERIVATIVES; CONSTRUCTION; SYSTEM; ESTERS; PHASE;

D O I：

10.3762/bjoc.18.130

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electrochemical preparation of 2-aminothiazoles has been achieved by the reaction of active methylene ketones with thioureas assisted by ᴅʟ-alanine using NH4I as a redox mediator. The electrochemical protocol proceeds in an undivided cell equipped with graphite plate electrodes under constant current conditions. Various active methylene ketones, including 13-keto ester, 13-keto amide, 13-keto nitrile, 13-keto sulfone and 1,3-diketones, can be converted to the corresponding 2-aminothiazoles. Mechanistically, the in situ generated alpha-iodoketone was proposed to be the key active species.

引用

页码：1249 / 1255

页数：7

共 42 条

[1] A Simple and Efficient Method for the Synthesis of 2-Aminothiazoles Under Mild Conditions [J].

Abedi-Jazini, Z. ;

Safari, J. ;

Zarnegar, Z. ;

Sadeghi, M. .

POLYCYCLIC AROMATIC COMPOUNDS, 2018, 38 (03) :231-235

[2] Synthesis of novel biologically active thiazole dyes and their applications [J].

Abu-Melha, Sraa .

PIGMENT & RESIN TECHNOLOGY, 2019, 48 (05) :375-382

[3] Eelectrosynthesis of benzothiazole derivatives via C-H thiolation [J].

Ahdenov, Reza ;

Mohammadi, Ali Asghar ;

Makarem, Somayeh ;

Taheri, Salman ;

Mollabagher, Hoda .

HETEROCYCLIC COMMUNICATIONS, 2022, 28 (01) :67-74

[4] Synthesis and liquid crystalline properties of models and polymers containing thiazolo[5,4-d]thiazole and siloxane flexible spacers [J].

Al-Dujaili, AH ;

Atto, AT ;

Al-Kurde, AM .

EUROPEAN POLYMER JOURNAL, 2001, 37 (05) :927-932

[5] On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate.: Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes [J].

Alajarin, Mateo ;

Cabrera, Jose ;

Pastor, Aurelia ;

Sanchez-Andrada, Pilar ;

Bautista, Delia .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5328-5339

[6] Recent developments of 2-aminothiazoles in medicinal chemistry [J].

Das, Debasis ;

Sikdar, Papiya ;

Bairagi, Moumita .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 109 :89-98

[7] One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid [J].

de Andrade, Vitor S. C. ;

de Mattos, Marcio C. S. .

SYNTHESIS-STUTTGART, 2018, 50 (24) :4867-4874

[8] Synthesis of 2-Aminothiazole Derivatives in Easy Two-Step, One-Pot Reaction [J].

Dziuk, Blazej ;

Kyziol, Janusz B. ;

Zaleski, Jacek ;

Ejsmont, Krzysztof ;

Zarychta, Bartosz .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (03) :763-768

[9] Recent advances in the electrochemical construction of heterocycles [J].

Francke, Robert .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :2858-2873

[10] Organic electrosynthesis: a promising green methodology in organic chemistry [J].

Frontana-Uribe, Bernardo A. ;

Little, R. Daniel ;

Ibanez, Jorge G. ;

Palma, Agustin ;

Vasquez-Medrano, Ruben .

GREEN CHEMISTRY, 2010, 12 (12) :2099-2119

← 1 2 3 4 5 →