| Synthesis of 3-benzo[d]imidazolylthio-methyl-4-arylideneisoxazol-5(4H)-ones |
| کد مقاله : 1145-ICOC |
| نویسندگان |
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رویا سلیم زاده *1، حمزه کیانی2، مصطفی ریاحی2 1دانشجوی دانشگاه شهرکرد 2هیات علمی دانشگاه شهرکرد |
| چکیده مقاله |
| Introduction: Isoxazoles represent a significant class of organic compounds, well known for their wide range of pharmaceutical applications. These heterocycles are particularly appreciated in drug discovery for the synthesis of a library of compounds and studying structure-activity relationships and biological effects. Isoxazole rings are widely found in natural products, biologically active compounds, and materials. Thus, great efforts have been devoted to their synthesis. Isoxazole derivatives have been synthesized via diverse methods using various acidic, basic, metallic, and organocatalytic conditions [1-3]. The development of novel, environmentally benign methods for constructing isoxazole derivatives has become a central goal of sustainable chemistry [4]. Methods: To an aqueous solution of equal amounts of arylaldehydes, ethyl 4-chloro-3-oxobutanoate, and hydroxylamine hydrochloride, KCl catalyst was added, and the reaction mixture was stirred at room temperature for a specified period. The reaction conditions were also optimized, and the best conditions were applied to the efficient synthesis of 3-chloromethyl-4-arylmethylideneisoxazol-5(4H)-ones. Then, the pre-synthesized chloromethylisoxazolones were reacted with 2-mercaptobenzoxazole, and the desired heterocyclic compounds were synthesized in acetonitrile solvent using potassium carbonate (Scheme 1). Results: The potassium chloride is found to possess acceptable catalytic activity for the promotion of three-component cyclocondensation for the construction of 3-chloromethylisoxazolones. Novel arylideneisoxazole-thiobenzoxazole hybrids were synthesized. The better yields were obtained when acetonitrile was used as a solvent. The structures of the expected products were determined using 1H-, 13C NMR, and IR spectroscopy. Conclusion: The novel compounds were obtained with modest to moderate yield. The reaction was promoted by the inexpensive reagent K2CO3 in acetonitrile under heating conditions. |
| کلیدواژه ها |
| Arylideneisoxazole, Chloromethylisoxazolone, 2-Mercaptobenzoxazole |
| وضعیت: پذیرفته شده |