Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW12O40 as Catalyst

doi:10.6023/cjoc201212039

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (07): 1540-1544.DOI: 10.6023/cjoc201212039 Previous Articles Next Articles

Notes

无溶剂超声辐射下磷钨酸铈催化合成5-亚烃基-2,2-亚戊基-1,3-二噁烷-4,6-二酮

许招会, 林春花

江西师范大学化学化工学院南昌 330027

收稿日期:2012-12-23 修回日期:2013-03-06 发布日期:2013-03-14
通讯作者: 许招会 E-mail:gotoxzh@tom.com
基金资助:
国家科技攻关计划(No. 2001BA323C)和江西省研究生创新基金(No. YC10A051)资助项目.

Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW₁₂O₄₀ as Catalyst

Xu Zhaohui, Lin Chunhua

Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027

Received:2012-12-23 Revised:2013-03-06 Published:2013-03-14
Supported by:
Project supported by the National Science and Technology Project (No. 2001BA323C) and the Graduate Innovation Fundation of Jiangxi Province (No. YC10A051).

Eight kinds of 5-alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones were synthesized by the Knoevenagel condensation reaction of aromatic aldehydes with 2,2-pentamethylene-1,3-dioxane-4,6-dione using CePW₁₂O₄₀ as catalyst, without solvent under ultrasonic irradiation. The results indicate that the yields ranged from 87.6% to 94.1% when using 5% (molar fraction) CePW₁₂O₄₀ and reacting at room temperature for 20～35 min. Furthermore, a proposed reaction mechanism for the reaction catalyzed by CePW₁₂O₄₀ was speculated. Compared to the classical Knoevenagel condensation reaction, the main advantages of the present procedure were milder conditions, shorter reaction time and higher yields, which afforded an effective method to synthesize 5-alkenyl-isopropylidene malonate derivatines. Further study showed that CePW₁₂O₄₀ was environmentally friendly and reused for four times without any noticeable decrease in the catalytic activity.

Key words: 2,2-pentamethylene-1,3-dioxane-4,6-dione, CePW₁₂O₄₀, aromatic aldehydes, condensation reaction

Cite this article

Xu Zhaohui, Lin Chunhua. Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW₁₂O₄₀ as Catalyst[J]. Chin. J. Org. Chem., 2013, 33(07): 1540-1544.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Jacobs, R. T.; Wright, A. D.; Smith, F. X. J. Org. Chem. 1982, 47, 3769.
[2] Bruns, R.; Wernicke, A.; Koll, P. Tetrahedron 1999, 55, 9793.
[3] Huang, Z.-Z.; Wu, L.-L.; Huang, X. Chin. J. Org. Chem. 2000, 20, 88 (in Chinese). (黄志真, 吴露玲, 黄宪, 有机化学, 2000, 20, 88.)
[4] Watanabe, T.; Knöpfel, T. F.; Carreira, E. M. Org. Lett. 2003, 5, 4557.
[5] Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899.
[6] Huang, X.; Xie, L. Synth. Commun. 1988, 18, 1701.
[7] Desai, U. V.; Pore, D. M.; Mane, R. B.; Solabannavao, P. P. Synth. Commun. 2004, 34, 25.
[8] Rao, P. S.; Venkataratnam, R. V. Tetrahedron Lett. 1991, 32, 5821.
[9] Davidson, D.; Bernhard, S. A. J. Am. Chem. Soc. 1948, 70, 3426.
[10] Corey, E. J. J. Am. Chem. Soc. 1952, 74, 5897.
[11] Kraus, G. A.; Krolski, M. E. J. Org. Chem. 1986, 51, 3347.
[12] Scuster, P.; Polansky, O. E.; Wessely, F. Monatsch. Chem. 1964, 95, 53.
[13] Dumas, A. M.; Seed, A.; Zorzitto, A. K.; Fillion, E. Tetrahedron Lett. 2007, 48, 7072.
[14] Feng, R.; Zhao, Y. Y.; Bao, C. G. Ultrason. Sonochem. 1997, 4, 183.
[15] Mikkol, J. P.; Salmi, T. Catal. Today 2001, 64, 271.
[16] Ambulgekar, G. V.; Bhanage, B. M.; Samant, S. D. Tetrahedron Lett. 2005, 46, 2483.
[17] Xu, Z.-H.; Liao, W.-L; Wang, S. Chin. J. Mol. Catal. 2008, 22, 39 (in Chinese). (许招会, 廖维林, 王甡, 分子催化, 2008, 22, 39.)
[18] Xu, Z.-H.; Liao, W.-L; Tu, Y.-H.; Wang, S. Chin. J. Rare Metals 2008, 32, 220. (许招会, 廖维林, 涂缘鸿, 王甡, 稀有金属, 2008, 32, 220.)
[19] Yan, N.; Xiong, B.; Liao, W.-L.; Xu, Z.-H. Chin. J. Org. Chem. 2010, 30, 1391 (in Chinese). (严楠, 熊斌, 廖维林, 许招会, 有机化学, 2010, 30, 1391.)
[20] Xu, F.-P.; Ding, W.-F.; Zhu, B.-L. J. Shanghai Univ. Sci. Technol. 1991, 2, 96 (in Chinese). (徐福培, 丁维钰, 竺宝林, 上海科学技术大学学报, 1991, 2, 96.)

无溶剂超声辐射下磷钨酸铈催化合成5-亚烃基-2,2-亚戊基-1,3-二噁烷-4,6-二酮

Solvent-Free Synthesis of 5-Alkenyl-2,2-pentamethylene-1,3-dioxane-4,6-diones under Ultrasonic Irradiation with CePW₁₂O₄₀ as Catalyst

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	JIan Xiao, Zhiying Wu, Ziyi Chen, Pengfei Zhao. Tetraethylenepentamine Functionalized Phenolic Resin as Highly Active Acid-Base Bifunctional Catalyst for Knoevenagel Condensation Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1179-1187.
[2]	Ren Xinfeng, Song Xiaoping, Ma Yingchao, Li Ya. Method for the Synthesis of 1,1-Dichloroalkenes [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1388-1393.
[3]	Wang Lingfeng, Qian Ying. Near-Infrared Quinoline-Fluoroborodipyrrole Dye: Synthesis and Lysosomal Fluorescence Imaging [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1246-1250.
[4]	Lu Yuhan, Han Yingzhi, Sun Yadong, Abdukader Ablimit, Wang Duozhi, Liu Chenjiang. Application of Iodobenzene Acetate Promoted Oxidation in the Synthesis of 2-Amino-1,3,4-thiadiazole Molecules [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 447-453.
[5]	Zhang Wenfeng, Xu Zhaohui, Tu Yuanhong, Liao Chuanwen. Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water [J]. Chin. J. Org. Chem., 2017, 37(9): 2449-2453.
[6]	Lin Chunhua, Yuan Jianjun, Liu Deyong, Zhang Houfu, Xu Zhaohui. Efficient Synthesis of 5,5-(Phenylmethylene)bis(2,2-dimethyl-1,3-dioxane-4,6-dione) Derivatives in Biobased Gluconic Acid Aqueous Solution [J]. Chin. J. Org. Chem., 2017, 37(6): 1560-1564.
[7]	Zhang Xun, Yang Nianfa. Poly[(S)-3-acrylamide-2,2'-dihydroxy-1,1'-binaphthyl]: Synthesis and Application in the Asymmetric Addition of Diethylzinc to Aromatic Aldehydes [J]. Chin. J. Org. Chem., 2017, 37(4): 1027-1032.
[8]	Peng Lifen, Jiang Juan, Peng Chao, Dai Ningning, Tang Zilong, Jiao Yinchun, Chen Jinyang, Xu Xinhua. Synthesis of Unsymmetrical Aromatic Acetylenes by Diphenyl Chlorophosphate-Promoted Condensation Reaction of Aromatic Aldehydes and Sulfones [J]. Chin. J. Org. Chem., 2017, 37(11): 3013-3018.
[9]	Wei Li, Chen Xuwen, Liu Yunyun, Wan Jieping. Recent Advances in Organic Synthesis Employing Ethyl Lactate as Green Reaction Medium [J]. Chin. J. Org. Chem., 2016, 36(5): 954-961.
[10]	Xu Zhaohui, Zhou Peng, Liu Deyong. Efficient One-Pot Synthesis of 3,3-Dimethyl-diphenyl-2,4-dioxa-8,10-diazaspiro[5.5]undecane-1,5-dione-9-thione Derivatives [J]. Chin. J. Org. Chem., 2016, 36(5): 1099-1103.
[11]	Xu Zhaohui, Tu Yuanhong. Solvent-Free Synthesis of Spiro Heterobicyclic Derivatives under Ultrasonic Irradiation with Dawson-Type Tungsten Vanado Phosphoric Heteropoly Acid as Catalyst [J]. Chin. J. Org. Chem., 2015, 35(6): 1357-1362.
[12]	Chen Jinfang, Xu Xiaoliang, Li Xiaonian. Research Development on the Condensation Reaction of Conjugated Olefine Acid and Polyethylene Glycol [J]. Chin. J. Org. Chem., 2015, 35(1): 39-54.
[13]	Wang Wenli, He Qing, Ding Ru, He Yun, Zhang Zunting. Synthesis of 1-Hydroxy-2-phenyltriphenylene Derivatives by Three-Step Condensation [J]. Chin. J. Org. Chem., 2014, 34(9): 1875-1880.
[14]	Xu Zhaohui. Solvent-Free Synthesis of 5-[(Indol-3-yl)-methyl]-2,2-dimethyl-1,3- dioxane-4,6-dione Derivatives under Ultrasonic Irradiation with Succinimide-N-sulfonic Acid Cerium as Catalyst [J]. Chin. J. Org. Chem., 2014, 34(8): 1687-1691.
[15]	Li Zhongxian, Wang Junwei, Zhao Junhong, Zhao Canfang, Liu Xiaopei, Yu Xuejun. Advanced in the Synthesis of Triarylmethanes [J]. Chin. J. Org. Chem., 2014, 34(3): 485-494.