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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.
【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.
- 【会议录名称】 中国化学会·第十五届全国有机合成化学学术研讨会会议论文集
- 【会议名称】中国化学会·第十五届全国有机合成化学学术研讨会
- 【会议时间】2018-08-02
- 【会议地点】中国甘肃兰州
- 【分类号】O626
- 【主办单位】中国化学会、国家自然科学基金委员会