Triphenylphosphane: An Efficient Catalyst for Three-Component Synthesis of Arylmethylidene-isoxazole-5(4H)-ones in Green Medium
Publish place: 26th Iranian Seminar on Organic Chemistry
Publish Year: 1397
نوع سند: مقاله کنفرانسی
زبان: English
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شناسه ملی سند علمی:
ISOC26_051
تاریخ نمایه سازی: 2 شهریور 1398
Abstract:
Heterocycles are obtaining more importance in recent years due to their pharmacological activities.The isoxazole core is a significant synthetic line of attack in drug discovery, and playsa significant role in arena of natural products, agrochemicals, and medicinal chemistry [1].Compounds containing this scaffold exhibit versatile biological properties such as antibacterial,anti-obesity, anti-inflammatory, antifungal, analgesic, and fungicidal activities [2]. Conventionalmethods for the synthesis of arylmethylidene-isoxazole-5(4H)-ones are the cyclizationof O-propioloyl oximes, the reaction of ethyl acetoacetate and hydroxylamine hydrochloridefollowed condensation with aromatic aldehydes, and condensation of 1,3-dicarbonylswith benzaldoximes. Significant development has been made in reviewing different routes forthe construction of an arylmethylidene-isoxazole-5(4H)-one skeleton [2-3]. A highly yieldingapproach for the synthesis of arylmethylidene-isoxazole-5(4H)-ones has been established usingtiphenylphosphane as the efficient catalyst. Here, the three-component reaction of ethylacetoacetate, various aromatic aldehydes, and hydroxylamine hydrochloride, under aqueousconditions at room temperature is described. This procedure has expectant features, includingshorter reaction times, easy separation of pure products with high yields, simplicity experimentalprocedure, operationally simple, and eco-friendly.
Authors
Ziba Daroughehzadeh
School of Chemistry, Damghan University, Damghan, Iran
Hamzeh Kiyani
School of Chemistry, Damghan University, Damghan, Iran