Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG1000-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System

doi:10.1007/s40242-013-3087-6

高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (5): 879-883.doi: 10.1007/s40242-013-3087-6

Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System

WANG Ying-lei¹, LUO Jun¹, ZHI Hui-zhen²

1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China;
2. School of Chemical and Materials Science, Nanjing Normal University, Nanjing 210046, P. R. China

收稿日期:2013-03-04 修回日期:2013-04-03 出版日期:2013-10-01 发布日期:2013-09-17
通讯作者: LUO Jun E-mail:luojun@njust.edu.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21002050).

Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System

WANG Ying-lei¹, LUO Jun¹, ZHI Hui-zhen²

1. School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. China;
2. School of Chemical and Materials Science, Nanjing Normal University, Nanjing 210046, P. R. China

Received:2013-03-04 Revised:2013-04-03 Online:2013-10-01 Published:2013-09-17
Contact: LUO Jun E-mail:luojun@njust.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21002050).

摘要/Abstract

摘要：

A facile and efficient protocol for the synthesis of 3,4-dihydropyrimidones via one-pot Biginelli reaction in PEG₁₀₀₀-DAIL/toluene system was developed. PEG₁₀₀₀-DAIL/toluene mixture is a temperature-driven reversible biphasic system, which promises the fully display of catalytic activity and simple recycle of PEG₁₀₀₀-DAIL. As a result, PEG₁₀₀₀-DAIL/toluene mixture showed catalyst-medium double-duty in the Biginelli reaction and afforded corresponding 3,4-dihydropyrimidones in excellent yields of 80%―95% for 20 examples. No obvious loss of catalytic activity was observed even after 10 recycling runs.

关键词: Thermoregulated biphase, Ionic liquid, Multicomponent reaction, Biginelli reaction, Green chemistry, Catalysis

Abstract:

Key words: Thermoregulated biphase, Ionic liquid, Multicomponent reaction, Biginelli reaction, Green chemistry, Catalysis

WANG Ying-lei, LUO Jun, ZHI Hui-zhen. Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System[J]. 高等学校化学研究, 2013, 29(5): 879-883.

参考文献

[1] Agbaje O. C., Fadeyi O. O., Fadeyi S. A., Myles L. E., Okoro C. O., Bioorg. Med. Chem. Lett., 2011, 21, 989
[2] Chitra S., Devanathan D., Pandiarajan K., Eur. J. Med. Chem., 2010, 45, 367
[3] Biginelli P., Gazz. Chim. Ital., 1893, 23, 360
[4] Suresh, Jagir S. S., Arkivoc, 2012, i, 66
[5] Abdelmadjid D., Boudjemaa B., Mouna A., Ali B., Salah R., Bertrand C., Tetrahedron Lett., 2006, 47, 5697
[6] Chen W. Y., Qin S. D., Jin J. R., Catal. Commun., 2007, 8, 123
[7] Salehi P., Dabiri M., Zolfigol M. A., Bodaghi F. M. A., Tetrahedron Lett., 2003, 44, 2889
[8] Yu Y., Liu D., Liu C., Luo G., Bioorg. Med. Chem. Lett., 2007, 17, 3508
[9] Brindaban C. R., Alakananda H., Umasish J., J. Org. Chem., 2000, 65, 6270
[10] Chitra S., Pandiarajan K., Tetrahedron Lett., 2009, 50, 2222
[11] Fu N. Y., Yuan Y. F., Cao Z., Wang S. W., Wang J. T., Clovis P., Tetrahedron, 2002, 58, 4801
[12] Li D. P., Mao H. F., An L. T., Huang Z. H., Zou J. P., Chin. J. Chem., 2010, 28, 2025
[13] Salehi H., Guo Q. X., Chin. J. Chem., 2005, 23, 91
[14] Heravi M. M., Bakhtiari K., Bamoharram F. F., Catal. Commun., 2006, 7, 373
[15] Suresh D. S., Krishnacharya G. A., Catal. Commun., 2011, 12, 1153
[16] Ajay K. B., Suhas P., Subhendu N. G., Goutam C., Maghar S. M., Tetrahedron Lett., 2004, 45, 8351
[17] Pasunooti K. K., Chai H., Jensen C. N., Gorityala B. K., Wang S. M., Liu X. W., Tetrahedron Lett., 2011, 52, 80
[18] Liu Q. J., Pan N., Xu J. H., Zhang W. W., Kong F. P., Synthetic Commun., 2013, 43, 139
[19] Priyanka G. M., Ratnadeep S. J., Deepak R. N., Charansingh H. G., Tetrahedron Lett., 2010, 51, 3138
[20] Li B. L., Ge C. H., Ying A. G., Adv. Mater. Res., 2012, 531, 428
[21] Jia X. D., Han S. Y., Duan H. F., Lin Y. J., Cao J. G., Liang D. P., Wu M. C., Chem. Res. Chinese Universities, 2013, 29(1), 82
[22] Lin C. X., Zhan H. Y., Liu M. H., Fu S. Y., Lucia L., Chem. Res. Chinese Universities, 2013, 29(1), 159
[23] Wang Z. T., Wang S. C., Xu L. W., Helv. Chim. Acta, 2005, 88, 986
[24] Yadav L. D. S., Rai A., Rai V. K, Awasth C., Tetrahedron, 2008, 64, 1420
[25] Peng J. J., Deng Y. Q., Tetrahedron Lett., 2001, 42, 5917
[26] Li M., Guo W. S., Wen L. R., Li Y. F., Yang H. Z., J. Mol. Catal. A: Chem., 2006, 258, 133
[27] Suman L. J., Jomy K. J., Bir S., Catal. Lett., 2007, 115, 52
[28] Chen X. F., Peng Y. Q., Catal. Lett., 2008, 122, 310
[29] Fang D., Zhang D. Z., Liu Z. L., Monatsh. Chem., 2010, 141, 419
[30] Banothu J., Somarapu V. L., Bavanthu R., Heterocycl. Commun., 2012, 18, 93
[31] Liu N., Liu C., Yan B., Jin Z. L., Appl. Organometal. Chem., 2011, 25, 168
[32] Ding Y., Zhao W., J. Mol. Catal. A: Chem., 2011, 337, 45
[33] Sunitha S., Kanjilal S., Reddy P. S., Rachapudi B. N., Tetrahedron Lett., 2007, 48, 6962
[34] David E. B., Christopher H., Chayanant H., J. Org. Chem., 2011, 76, 523
[35] Yang Y. C., Jiang J. Y., Wang Y. H., Liu C., Jin Z. L., J. Mol. Catal. A: Chem., 2007, 261, 288
[36] Sun Z., Wang Y. H., Niu M. M., Yi H. Q., Jiang J. Y., Jin Z. L., Catal. Commun., 2012, 27, 78
[37] Zeng Y., Wang Y. H., Jiang J. Y., Jin Z. L., Catal. Commun., 2012, 19, 70
[38] Xu Y. C., Wang Y. H., Zeng Y., Jiang J. Y., Jin Z. L., Catal. Lett., 2012, 142, 914
[39] Zhi H. Z., Lv C. X., Zhang Q., Luo J., Chem. Commun., 2009, 2878
[40] Zhi H. Z., Luo J., Ma W., Lv C. X., Chem. J. Chinese Universities, 2008, 29(10), 2007

Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System

Preparation of 3,4-Dihydropyrimidones via Biginelli Reaction in Efficient and Recyclable PEG₁₀₀₀-DAIL/Toluene Catalyst-mediumCombined Thermoregulated Biphasic System

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