期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2014, 期 31, 页码 6945-6952出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201402808
关键词
Synthetic methods; Selenium heterocycles; Selenium; Carboxylic acids
资金
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES)
- Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)
- Instituto Nacional de Ciencias e Tecnologia de Catalise em Sistemas Moleculares e Nanoestruturados (INCT-CMN)
- Fundacao de Amparo a Pesquisa do Estado do Rio Grande do Sul (FAPERGS) [PRONEM 11/2024-9]
- CNPq
We report a general, practical, and simple metal-free method for the synthesis of 2-substituted 1,3-benzoselenazoles by the reaction of bis(2-aminophenyl)diselenide with a wide range of carboxylic acids, promoted by tributylphosphine. This efficient reaction furnishes 2-aryl-1,3-benzoselenazoles in good yields and tolerates a variety of substituents at the aryl moiety of carboxylic acids. For the first time, 2-alkyl-1,3-benzoselenazoles could be obtained from aliphatic carboxylic acids and thiazolidine-4-carboxylic acid in high chemical yields. The use of focused microwave irradiation considerably decreased the reaction time from 48 to 2 h. The experimental data provide insights into the mechanism of the reaction.
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