One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones in Aqueous Media under Ultrasonic Irradiation

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (08): 1267-1271. Previous Articles Next Articles

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超声辐射下水介质中一锅合成3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮

程青芳*,a,b ; 许兴友a,b; 王启发c ; 刘丽莎b;
刘望军b; 林俏b ; 杨绪杰a

(a南京理工大学材料化学实验室南京 210094)
(b淮海工学院化学工程系连云港 222005)
(c淮海工学院江苏省海洋生物技术重点实验室连云港 222005)

收稿日期:2008-11-12 修回日期:2009-02-06 发布日期:2009-08-30
通讯作者: 程青芳

One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones in Aqueous Media under Ultrasonic Irradiation

Cheng, Qingfang^*,a,b ; Xu, Xingyou ^a,b; Wang, Qifa ^c; Liu, Lisha ^b;
Liu, Wangjun^b; Lin, Qiao ^b; Yang, Xujie ^a

(a Materials Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094) (b Department of Chemical Technology, Huaihai Institute of Technology, Lianyungang 222005) (c Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, Lianyungang 222005)

Received:2008-11-12 Revised:2009-02-06 Published:2009-08-30
Contact: Cheng, Qingfang

Abstract

One-pot three component condensation reactions of methyl acetoacetate, hydroxylamine hydrochloride and aromatic aldehydes were used for the preparation of a series of 3-methyl-4-arylmethylene- isoxazol-5(4H)-one derivatives under ultrasonic irradiation in aqueous media at room temperature. The third component may be aldehydes bearing electron-doner or electron-drawing groups, the one-pot condensation has been found to proceed efficiently at room temperature in good to medium yields under ultrasonic irradia-tion. The condensation of methyl acetoacetate, hydroxylamine hydrochloride with α,β-unsaturated, hetero aromatic aldehydes as well as p-phthalaldehyde also proceeded smoothly at room temperature in medium yields. The structures of the products were characterized by elemental analysis, IR, 1H NMR, and X-ray sin-gle crystal analysis. The work-up procedure is very simple and environmental friendliness.

Key words: ultrasonic irradiation, aqueous media, one-pot synthes, 3-methyl-4-arylmethylene-isoxazol-5(4H)-one

Cite this article

Cheng, Qingfang^*,a,b ; Xu, Xingyou ^a,b; Wang, Qifa ^c; Liu, Lisha ^b;
Liu, Wangjun^b; Lin, Qiao ^b; Yang, Xujie ^a
. One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones in Aqueous Media under Ultrasonic Irradiation[J]. Chin. J. Org. Chem., 2009, 29(08): 1267-1271.

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超声辐射下水介质中一锅合成3-甲基-4-芳亚甲基-异噁唑-5(4H)-酮

One-Pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones in Aqueous Media under Ultrasonic Irradiation

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