环氧查尔酮的制备及其与苯肼和脲的反应
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摘要
环氧查尔酮是一类重要的有机中间体，通过开环、缩合、加成等反应，可以转化为种类繁多的合成子，广泛应用于具有生理活性的天然产物、农药和药物的合成。
本文在总结本研究室近期研究工作的基础上，继续开展新的研究课题，拓宽其研究领域。综述了近几年来环氧查尔酮反应的进展；在超声辐射下，以过氧化氢为氧化剂由芳香醛和取代苯乙酮于乙醇中一锅法反应改进了环氧查尔酮的合成；以盐酸为催化剂由环氧查尔酮和苯肼于乙醇溶剂中合成1,3-二苯基-5-芳基吡唑；以KOH为催化剂由环氧查尔酮和脲(或硫脲)合成5-苯基-5-芳基甲基海因(或5-苯基-5-芳基甲基-2-硫代海因)，均取得预期效果，操作简便、条件温和、收率较高。由环氧查尔酮和苯肼在无溶剂条件下加热回流合成1,3-二苯基-5-芳基吡唑也获得良好结果。
Epoxychalcones are very important synthetic intermediates and can serve as versatileprecursors in synthesis of many natural products, pesticide and drug molecules.
Based on the previous work of our laboratory, some new approaches to the synthesis ofthe heterocyclic compounds were explored to extend research field. In this paper, we presentesome results as follows: Under ultrasound irradiation, the synthesis of epoxychalcone via theone-pot way reactions of acetophenones and arylaldehydes oxidated by aqueous hydrogenperoxide in ethanol, the synthesis of 5-aryl-1,3-diphenylpyrazole via the reactions ofepoxychalcone and phenylhydrazine catalyzed by HCl and the synthesis of 5-phenyl-5-arylmethylhydantoin (or 5-phenyl-5-arylmethy-2-thiol hydantoin) via the reactions ofepoxylchalcone with urea(or thiourea) catalyzed by KOH in ethanol at 50 oC. Epoxylchalconeand phenylhydrazine reacted to synthesize 1,3-diphenyl-5-arylpyrazoles at 230 oC undersolvent-free condition also give a favorable result.
本文在总结本研究室近期研究工作的基础上，继续开展新的研究课题，拓宽其研究领域。综述了近几年来环氧查尔酮反应的进展；在超声辐射下，以过氧化氢为氧化剂由芳香醛和取代苯乙酮于乙醇中一锅法反应改进了环氧查尔酮的合成；以盐酸为催化剂由环氧查尔酮和苯肼于乙醇溶剂中合成1,3-二苯基-5-芳基吡唑；以KOH为催化剂由环氧查尔酮和脲(或硫脲)合成5-苯基-5-芳基甲基海因(或5-苯基-5-芳基甲基-2-硫代海因)，均取得预期效果，操作简便、条件温和、收率较高。由环氧查尔酮和苯肼在无溶剂条件下加热回流合成1,3-二苯基-5-芳基吡唑也获得良好结果。
Epoxychalcones are very important synthetic intermediates and can serve as versatileprecursors in synthesis of many natural products, pesticide and drug molecules.
Based on the previous work of our laboratory, some new approaches to the synthesis ofthe heterocyclic compounds were explored to extend research field. In this paper, we presentesome results as follows: Under ultrasound irradiation, the synthesis of epoxychalcone via theone-pot way reactions of acetophenones and arylaldehydes oxidated by aqueous hydrogenperoxide in ethanol, the synthesis of 5-aryl-1,3-diphenylpyrazole via the reactions ofepoxychalcone and phenylhydrazine catalyzed by HCl and the synthesis of 5-phenyl-5-arylmethylhydantoin (or 5-phenyl-5-arylmethy-2-thiol hydantoin) via the reactions ofepoxylchalcone with urea(or thiourea) catalyzed by KOH in ethanol at 50 oC. Epoxylchalconeand phenylhydrazine reacted to synthesize 1,3-diphenyl-5-arylpyrazoles at 230 oC undersolvent-free condition also give a favorable result.
引文
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