Synthesis of novel substituted 2-aryl-3-(3’-oxobutenyl)benzoxazole

【作者】 Kaixuan Wang； 王兰芝；

【Author】 Kaixuan Wang;Lanzhi Wang;The College of Chemistry and Material Science, Hebei Normal University;

【机构】 The College of Chemistry and Material Science, Hebei Normal University； 河北师范大学；

【摘要】 N-Heterocyclic compounds are the main building blocks in synthetic organic chemistry.Especially,benzoxazole derivatives have attracted considerable attention because of their wide variety of applications in agrochemicals, natural products, functional materials and pharmaceutically active molecules¹.Some of the benzoxazole derivatives, which are already booming in the market, to quote a few, pseudopteroxazole（antimicrobial agent）, UK-1（anticancer agent）, flunoxaprofen（NSAID）, tafamidis（hereditary amyloidosis）².Owing to such significance,the synthesis of benzoxazole and its derivatives has been an attractive goal for organic and medicinal chemists.Therefore, we designed and synthesized a series of unreported novel substituted 2-aryl-3-（3’-oxobutenyl）benzoxazole in three steps.The intermediates（5a-5i） were obtained via the condensation reaction of 2-aminophenol（1） with para-substituted benzaldehyde（2） and 3-butyn-2-one（4） under CH₃CH₂OH at ambient temperature.Treatment of intermediates 5 in the presence of a catalytic amount of CH₃COOH in CH₂Cl₂ at 25℃ resulted in the formation of the 2-aryl-3-（3’-oxobutenyl）benzoxazole（6a～6i） in 90% yield（Scheme 1）.The target compounds were determined by ¹HNMR, ¹³CNMR, MS, IR and elemental analysis.更多还原

【Abstract】 N-Heterocyclic compounds are the main building blocks in synthetic organic chemistry.Especially,benzoxazole derivatives have attracted considerable attention because of their wide variety of applications in agrochemicals, natural products, functional materials and pharmaceutically active molecules¹.Some of the benzoxazole derivatives, which are already booming in the market, to quote a few, pseudopteroxazole（antimicrobial agent）, UK-1（anticancer agent）, flunoxaprofen（NSAID）, tafamidis（hereditary amyloidosis）².Owing to such significance,the synthesis of benzoxazole and its derivatives has been an attractive goal for organic and medicinal chemists.Therefore, we designed and synthesized a series of unreported novel substituted 2-aryl-3-（3’-oxobutenyl）benzoxazole in three steps.The intermediates（5a-5i） were obtained via the condensation reaction of 2-aminophenol（1） with para-substituted benzaldehyde（2） and 3-butyn-2-one（4） under CH₃CH₂OH at ambient temperature.Treatment of intermediates 5 in the presence of a catalytic amount of CH₃COOH in CH₂Cl₂ at 25℃ resulted in the formation of the 2-aryl-3-（3’-oxobutenyl）benzoxazole（6a～6i） in 90% yield（Scheme 1）.The target compounds were determined by ¹HNMR, ¹³CNMR, MS, IR and elemental analysis.更多还原