A Facile and Efficient Synthesis of 3-Carbonitrile Pyridin-2(1H)-one Derivatives under Solvent-Free Conditions

doi:10.6023/cjoc1104143

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (02): 400-403 .DOI: 10.6023/cjoc1104143 Previous Articles Next Articles

Notes

无溶剂条件下方便、有效的方法合成3-氰基-2-吡啶酮衍生物

荣良策^a,b, 刘丽华^a, 殷姗^b, 夏盛^b, 魏贤勇^a, 宗志敏^a

a 中国矿业大学化工学院徐州 221008;
b 徐州师范大学化学化工学院徐州 221116

收稿日期:2011-04-14 修回日期:2011-07-21 发布日期:2012-03-09
通讯作者: 魏贤勇 E-mail:lcrong@xznu.edu.cn or lcrong2005@yahoo.com
基金资助:
江苏省高校自然科学基础研究基金(No. 08KJB150017)、徐州师范大学科研平台(No. 10XLS02)资助项目.

A Facile and Efficient Synthesis of 3-Carbonitrile Pyridin-2(1H)-one Derivatives under Solvent-Free Conditions

Rong Liangce^a,b, Liu Lihua^a, Yin Shan^b, Xia Sheng^b, Wei Xianyong^a, Zong Zhimin^a

a School of Chemical Engineering and Technology, China University of Mining and Technology,Xuzhou 221008;
b College of Chemistry and Chemical Engineering, Xuzhou Normal University Xuzhou 221116

Received:2011-04-14 Revised:2011-07-21 Published:2012-03-09
Supported by:
Project supported by the Natural Science Foundation of Jiangsu Education Department (No. 08KJB150017), and the Research Platform Foundation of Xuzhou Normal University (No. 10XLS02).

An efficient and convenient method for the preparation of 3-carbonitrile pyridin-2(1H)-one derivative by the one-pot reaction of aromatic aldehydes, acetones and 2-cyanoacetamide in the presence of sodium hydroxide under solvent- free condition was reported. This method has the advantages of excellent yields, mild reaction conditions, easy work-up, and environmentally friendly procedure.

Key words: pyridin-2(1H)-one, heterocycle, solvent-free reaction, synthesis

Cite this article

Rong Liangce, Liu Lihua, Yin Shan, Xia Sheng, Wei Xianyong, Zong Zhimin. A Facile and Efficient Synthesis of 3-Carbonitrile Pyridin-2(1H)-one Derivatives under Solvent-Free Conditions[J]. Chin. J. Org. Chem., 2012, 32(02): 400-403 .

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[1] Cottineau, B.; Toto, P.; Marot, C.; Pipaud, A.; Chenault, J. Bioorg. Med. Chem. Lett. 2002, 12, 2105.

[2] Lee, K. Y.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2003, 44, 6737.

[3] Jia, Z. J.; Wu, Y.; Huang, W.; Zhang, P.; Song, Y.; Woolfrey, J.; Sinha, U.; Arfsten, A.; Edwards, S.; Hutchaleelaha, A.; Hollennbach, S.; Lambing, J.; Scarborough, R.; Zhu, B. Y. Bioorg. Med. Chem. Lett. 2004, 14, 1229.

[4] John, W. L.; Patera, R. M.; Plunner, M. J.; Halling, B. P.; Yuhas, D. A. Pestic. Sci. 1994, 42, 29.

[5] (a) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435. (b) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633.

[6] Pastelin, G.; Mendez, R.; Kabela, E; Farah, A. Life Sci. 1983, 33, 1787.

[7] Angibaud, P. R.; Venet, M. G.; Filliers, W.; Broeckx, R.; Ligny, Y. A.; Muller, P.; Poncelet, V. S.; End, D. W. Eur. J. Org. Chem. 2004, 479.

[8] (a) Huth, A.; Schmiechen, R.; Moto, L.; Beetz, I.; Breitkopf, A.; Frost, E.; Schumann, I.; Thielert, K. Arch. Pharm. 1988, 321, 297. (b) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304.

[9] Li, W. W.; Chen, Y.; Lam, Y. Tetrahedron Lett. 2004, 45, 6545.

[10] Gorobert, N. Y.; Yousefi, B. H.; Belaj, F.; Kaffe, C. O. Tetrahedron 2004, 60, 8633.

[11] Oberg, K. M.; Lee, E. E.; Rovis, T. Tetrahedron 2009, 69, 5056.

[12] Svetlik, J.; Kettmann, V.; Zaleska, B. Tetrahedron Lett. 2005, 46, 5511.

[13] Mont, N.; Teixido, J.; Borrell, J. I.; Kappe, C. O. Tetrahedron Lett. 2003, 44, 5385.

[14] Laschat, S.; Dickner, T. Synthesis 2000, 1781.

[15] Tanaka, T.; Toda, F. Chem. Rev. 2000, 100, 1025.

[16] Rong, L. C.; Han, H. X.; Jiang. H.; Tu, S. J. Synth. Commun. 2009, 39, 1027.

[17] Gao, L. J.; Ji, H. L.; Rong, L. C.; Han, H. X.; Shi, Y. H.; Tu, S. J. J. Heterocycl. Chem., 2010, 47, 358.

[18] Zhang, G. P.; Xia, Y. Chin. J. Org. Chem. 2010, 30, 449 (in Chinese). (张国平, 夏燕, 有机化学, 2010, 30, 449.)

[19] Yu Y.; Guo, H. Y. Chin. J. Org. Chem. 2011, 31, 96 (in Chinese). (余意, 郭红云, 有机化学, 2011, 31, 96.)

无溶剂条件下方便、有效的方法合成3-氰基-2-吡啶酮衍生物

A Facile and Efficient Synthesis of 3-Carbonitrile Pyridin-2(1H)-one Derivatives under Solvent-Free Conditions

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