One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid

被引：22
作者：
de Andrade, Vitor S. C. [1 ]
de Mattos, Marcio C. S. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Inst Quim, Dept Quim Organ, CP 68545, BR-21974597 Rio De Janeiro, Brazil
来源：
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 24期
关键词：
heterocycles; condensation; thiazole; quinoxaline; green chemistry; tribromoisocyanuric acid; pot-ecomomy; thiourea; FACILE SYNTHESIS; N-PHENYLUREAS; 2-AMINOTHIAZOLES; ISOTHIOCYANATES; GREEN; ACID/TRIPHENYLPHOSPHINE; CHEMISTRY; REAGENT; DESIGN; SYSTEM;
D O I：
10.1055/s-0037-1610243
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A simple and efficient one-zpot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for alpha-mono-halogenation of beta-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced the corresponding 2-aminothiazoles in up to 87% yield. Extension of the reaction to thioacetamide and o-phenylenediamine led to 2-methylthiazole and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process.
引用
收藏
页码：4867 / 4874
页数：8
相关论文
共 53 条
[41]   Bioactive thiazole and benzothiazole derivatives [J].
Rouf, Abdul ;
Tanyeli, Cihangir .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :911-927
[42]   Efficient Direct Halogenation of Unsymmetrical N-Benzyl- and N-Phenylureas with Trihaloisocyanuric Acids [J].
Sanabria, Carlos M. ;
Costa, Bruno B. S. ;
Viana, Gil M. ;
de Aguiar, Lucia C. S. ;
de Mattos, Marcio C. S. .
SYNTHESIS-STUTTGART, 2018, 50 (06) :1359-1367
[43]   Highly Regioselective Iodination of N-Phenylureas with Iodine/Trichloroisocyanuric Acid [J].
Sanabria, Carlos M. ;
do Casal, Mariana T. ;
de Souza, Raphael B. A. ;
de Aguiar, Lucia C. S. ;
de Mattos, Marcio C. S. .
SYNTHESIS-STUTTGART, 2017, 49 (07) :1648-1654
[44]   Microwave-Assisted Domino Reactions of Propargylamines with Isothiocyanates: Selective Synthesis of 2-Aminothiazoles and 2-Amino-4-methylenethiazolines [J].
Scalacci, Nicolo ;
Pelloja, Chiara ;
Radi, Marco ;
Castagnolo, Daniele .
SYNLETT, 2016, 27 (12) :1883-1887
[45]   Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: An analogue-based drug design approach [J].
Sharma, Ritesh N. ;
Xavier, Franklin P. ;
Vasu, Kamala K. ;
Chaturvedi, Subhash C. ;
Pancholi, Shyam S. .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (03) :890-897
[46]   Appel Reaction of Carboxylic Acids with Tribromoisocyanuric Acid/Triphenylphosphine: a Mild and Acid-Free Preparation of Esters and Amides [J].
Sindra, Haryadylla da Cunha ;
de Mattos, Marcio C. S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2016, 27 (06) :1129-1136
[47]   Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles [J].
Tang, Xiaodong ;
Zhu, Zhongzhi ;
Qi, Chaorong ;
Wu, Wanqing ;
Jiang, Huanfeng .
ORGANIC LETTERS, 2016, 18 (02) :180-183
[48]   New 1,3-thiazole derivatives and their biological and ultrastructural effects on Trypanosoma cruzi [J].
Teixeira de Moraes Gomes, Paulo Andre ;
Barbosa, Miria de Oliveira ;
Santiago, Edna Farias ;
de Oliveira Cardoso, Marcos Verissimo ;
Capistrano Costa, Natali Tereza ;
Hernandes, Marcelo Zaldini ;
Magalhaes Moreira, Diogo Rodrigo ;
da Silva, Aline Caroline ;
Ramos dos Santos, Thiago Andre ;
Alves Pereira, Valeria Rego ;
Brayner dos Santos, Fabio Andre ;
do Nascimento Pereira, Glaecia Aparecida ;
Ferreira, Rafaela Salgado ;
Lima Leite, Ana Cristina .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 121 :387-398
[49]   Trihaloisocyanuric Acids/NaX: an environmentaly friendly system for vicinal dihalogenation of Alkenes without using molecular halogen [J].
Tozetti, Suellen D. F. ;
de Almeida, Leonardo S. ;
Esteves, Pierre M. ;
de Mattos, Marcio C. S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2007, 18 (04) :675-677
[50]   First example of the coupling of α-diazoketones with thiourea:: a novel route for the synthesis of 2-aminothiazoles [J].
Yadav, J. S. ;
Reddy, B. V. Subba ;
Rao, Y. Gopala ;
Narsaiah, A. V. .
TETRAHEDRON LETTERS, 2008, 49 (15) :2381-2383
123456