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Microwave-assisted efficient synthesis of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl via 1,3-dipolar cycloaddition.
Mol Divers ; 2019 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-31309395
ABSTRACT
An efficient strategy for synthesizing of 3-substituted bis-isoxazole ether bearing 2-chloro-3-pyridyl under microwave radiation was reported. The reactive regioselectivity was improved by changing mainly the solvent and acid-binding agent. 3-(2-Chloropyridin-3-yl)-5-(((3-substituted phenyl isoxazol-5-yl)methoxy)methyl)isoxazoles were synthesized in 31-92% yields and were characterized by FT-IR, HRMS, 1H and 13C NMR spectroscopy. The single crystal of 3-(2-chloropyridin-3-yl)-5-(((3-(p-tolyl)isoxazol-5-yl)methoxy)methyl)isoxazole was obtained, and the structure of compound has also been determined by X-ray diffraction technique. Weak intra- and intermolecular C-H∙∙∙O interactions and a C-H∙∙∙π interaction link molecules into a three-dimensional network. The results showed that the synthesized compounds belonged to triclinic system, and their regioselectivity depended on the solvent and acid-binding agent. The merits of this method include the environmentally friendly, efficient, simple operation, and higher regional selectivity. An efficient synthesis of 3-substituted bis-isoxazole ethers was developed via 1,3-dipolar cycloaddition reaction starting from 3-substituted phenyl-5-((prop-2-yn-1-yloxy))methyl)isoxazoles and (Z)-2-chloro-N-hydroxynicotinimidoyl chloride using NaHCO3 as an acid-binding agent in THF solvent-dissolved trace water under catalyst-free microwave-assisted conditions.

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Texto completo: Disponível Coleções: Bases de dados internacionais Base de dados: MEDLINE Idioma: Inglês Assunto da revista: Biologia Molecular Ano de publicação: 2019 Tipo de documento: Artigo