One-Pot Three-Component Synthesis of Pyrano[2,3-d]pyrimidine Derivatives in Aqueous Media under Ultrasonic Irradiation

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (07): 1138-1141. Previous Articles Next Articles

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超声辐射下水介质中三组分一锅合成吡喃并[2,3-d]嘧啶衍生物

程青芳^*,a,b; 许兴友^a,b ; 阮明杰^a ; 温艳玲^a; 何晓姜^a; 杨绪杰^b

(a淮海工学院化工系连云港 222005)
(b南京理工大学材料化学实验室南京 210094)

收稿日期:2008-09-12 修回日期:2008-12-15 发布日期:2009-07-22
通讯作者: 程青芳

One-Pot Three-Component Synthesis of Pyrano[2,3-d]pyrimidine Derivatives in Aqueous Media under Ultrasonic Irradiation

Cheng, Qingfang^*,a,b ; Xu, Xingyou ^a,b; Ruan, Mingjie ^a; Wen, Yanling^a;
He, Xiaojiang^a; Yang, Xujie^b

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

Received:2008-09-12 Revised:2008-12-15 Published:2009-07-22
Contact: Cheng, Qingfang

Abstract

One-pot three component condensation reactions of aromatic aldehydes, malononitrile, and barbituric acid were described for the preparation of a series of pyrano[2,3-d]pyrimidine derivatives under ultrasonic irradiation in aqueous media without catalyst. For the saturated aromatic aldehydes with malononitrile and barbituric acidit, the reaction was found to proceed very efficiently at room temperature giving excellent yields under ultrasonic irradiation, while for α,β-unsaturated aldehydes as well as p-phthalaldehyde with malononitrile and barbituric acid the reaction also proceeded smoothly at room temperature with good yields. The structures of the products were characterized by IR, 1H NMR spectra and elemental analyses. The work-up procedure is very simple and environmentally friendly.

Key words: one-pot synthesis, ultrasonic irradiation, aqueous media, pyrano[2,3-d]pyrimidine

Cite this article

Cheng, Qingfang^*,a,b ; Xu, Xingyou ^a,b; Ruan, Mingjie ^a; Wen, Yanling^a;
He, Xiaojiang^a; Yang, Xujie^b
. One-Pot Three-Component Synthesis of Pyrano[2,3-d]pyrimidine Derivatives in Aqueous Media under Ultrasonic Irradiation[J]. Chin. J. Org. Chem., 2009, 29(07): 1138-1141.

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超声辐射下水介质中三组分一锅合成吡喃并[2,3-d]嘧啶衍生物

One-Pot Three-Component Synthesis of Pyrano[2,3-d]pyrimidine Derivatives in Aqueous Media under Ultrasonic Irradiation

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