NOTE

Rapid and Efficient Ultrasound-Assisted Method for the Synthesis of 2-Thioxo-2H-thiopyran and 2-Amino-6-thioxodihydropyridine Derivatives

  • Lin Wei ,
  • Zheng Yongxiang ,
  • Huang Zhibin ,
  • Shi Daqing
Expand
  • a School of Chemistry and Environmental Engineering, Jiangsu Technology of University, Changzhou 213001;
    b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123

Received date: 2016-08-22

  Revised date: 2016-11-02

  Online published: 2016-11-17

Supported by

Project supported by the National Natural Science Foundation of China (No. 21502074) and the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 15KJA150006).

Abstract

A rapid and efficient ultrasound-assisted method for the synthesis of 2-thioxo-2H-thiopyran and 2-amino-6-thioxodihydropyridine derivatives by the reaction of 2-(1-phenylethylidene)malononitrile and carbon disulfide or isothiocy-anatobenzene catalyzed by NaOH has been developed. This protocol has the advantages of simple operation, short reaction times, high yields, and environmental friendliness. The structures of all the products were characterized by 1H NMR, 13C NMR, IR and MS techniques. The reported method is the efficient approach for the synthesis of 2-thioxo-2H-thiopyran and 2-amino-6-thi-oxodihydropyridine derivatives.

Cite this article

Lin Wei , Zheng Yongxiang , Huang Zhibin , Shi Daqing . Rapid and Efficient Ultrasound-Assisted Method for the Synthesis of 2-Thioxo-2H-thiopyran and 2-Amino-6-thioxodihydropyridine Derivatives[J]. Chinese Journal of Organic Chemistry, 2017 , 37(2) : 508 -513 . DOI: 10.6023/cjoc201608017

References

[1] Krauze, A.; Germane, S.; Eberlins, O. Eur. J. Med. Chem. 1999, 34, 301.
[2] (a) Brown, M. J.; Carter, P. S.; Fenwick, A. E.; Fosberry, A. P.; Hamprecht, D. W.; Hibbs, M. J.; Jarvest, R. L.; Mensah, L.; Milner, P. H.; O'Hanlon, P. J.; Pope, A. J.; Richardson, C. M.; West, A.; Witty, D. R. Bioorg. Med. Chem. Lett. 2002, 12, 3171.
(b) Quaglia, W.; Pigini, M.; Piergentili, A.; Giannella, M.; Gentili, F.; Marucci, G.; Carrieri, A.; Carotti, A.; Poggesi, E.; Leonardi, A.; Melchiorre, C. J. Med. Chem. 2002, 45, 1633.
(c) Sugita, Y.; Hosoya, H.; Terasawa, K.; Yokoe, I.; Fujisawa, S.; Sakagami, H. Anticancer Res. 2001, 21, 2629.
[3] Freifeld, L.; Shojael, H.; Langer, P. J. Org. Chem. 2006, 71, 4965.
[4] Eynde, J. J.; Defosse, F.; Mayence, A.; Haverbeke, Y. V. Tetrahedron 1995, 51, 6511.
[5] Sabitha, G.; Reddy, G. S. K. K.; Reddy, C. S.; Yadav, J. S. Tetrahedron Lett. 2003, 44, 4129.
[6] (a) Abbas, A. E.; Rahele, H. Phosphorus, Sulfur Silicon Relat. Elem. 2011, 186, 2267.
(b) Wang, W.; Li, H.; Wang, J.; Zu, L. J. Am. Chem. Soc. 2006, 128, 10354.
(c) Jagodziński, T. S.; So?nicki, J. G.; Wesolowska, A. Tetrahedron 2003, 59, 4183.
(d) Rios, R.; Sundén, H.; Ibrahem, L.; Zhao, G. L.; Eriksson, L.; Córdova, A. Tetrahedron Lett. 2006, 47, 8547.
(e) Krystyna, B. S.; Malgorzata, K. Monatsh. Chem. 2006, 137, 347.
[7] (a) Luche, J. L. Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.
(b) Ji, S. J.; Shi, D. Q. New Technology of Modern Organic Synthesis, Chemical Industry Press, Bejing, 2009 (in Chinese).(纪顺俊, 史达清, 现代有机合成新技术, 化学工业出版社, 北京, 2009.)
(c) Li, J. T.; Wang, S. X.; Chen, G. F.; Li, T. S. Curr. Org. Synth. 2005, 2, 425.
[8] (a) Wolfe, S.; Ingold, C. F. J. Am. Chem. Soc. 1983, 105, 7755.
(b) Peng, K.; Chen, F. X.; She, X. G.; Yang, C. H.; Cui, Y. X.; Pan, X. F. Tetrahedron Lett. 2005, 46, 1217.
[9] (a) Suslick, K. S.; Casadonate, D. J. Am. Chem. Soc. 1987, 109, 3459.
(b) Pasha, M. A.; Jayashankara, V. P. Ultrason. Sonochem. 2005, 12, 433.
[10] (a) Hofmann, J.; Freier, U.; Weeks, M. Ultrason. Sonochem. 2003, 10, 271.
(b) Meciarova, M.; Kiripolsky, M.; Toma, S. Ultrason. Sonochem. 2005, 12, 401.
(c) Martins, M. A. P.; Rossatto, M.; Prola, L. D. T.; Pizzuti, L.; Moreira, D. N.; Campos, P. T.; Frizzo, C. P.; Zanatta, N.; Bonacorso, H. G. Ultrason. Sonochem. 2012, 19, 227.
[11] Li, J. T.; Chen, G. F.; Xu, W. Z.; Li, T. S. Ultrason. Sonochem. 2003, 10, 115.
[12] (a) Li, J. T.; Yang, W. Z.; Wang, S. X.; Li, S. H.; Li, T. S. Ultrason. Sonochem. 2001, 4, 55.
(b) Zhang, Z. H.; Li, J. T.; Li, T. S. Ultrason. Sonochem. 2008, 15, 673.
[13] (a) Zhang, J.; Yang, F.; Ren, G.; Mark, T. C. W.; Song, M.; Wu, Y. Ultrason. Sonochem. 2008, 15, 115.
(b) Polackova, V.; Hutka, M.; Toma, S. Ultrason. Sonochem. 2005, 12, 99.
[14] (a) Tu, S. J.; Cao, L. J.; Zhang, Y.; Shao, Q. Q.; Zhou, D. X.; Li, C. M. Ultrason. Sonochem. 2008, 15, 217.
(b) Kumar, H.; Parmar, A. Ultrason. Sonochem. 2008, 15, 129.
(c) Zhou, G.; Liang, G. C.; Zhong, Y. F.; Han, X. Y.; Chen, G. F.; Song, Y. L. Chin. J. Org. Chem. 2016, 36, 143 (in Chinese).(周冠, 梁国超, 钟一凡, 韩晓燕, 陈国锋, 宋亚丽, 有机化学, 2016, 36, 143.)
[15] (a) Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H. L.; Shi, D. Q. Ultrason. Sonochem. 2011, 18, 708.
(b) Zou, Y.; Hu, Y.; Liu, H.; Shi, D. Q. ACS Comb. Sci. 2012, 14, 38.
(c) Hu, Y.; Zou, Y.; Wu, H.; Shi, D. Q. Ultrason. Sonochem. 2012, 19, 264.
(d) Yang, J. M.; Li, Q.; Zhang, J. J.; Lin, W.; Wang, J. X.; Wang, Y. C.; Huang, Z. B.; Shi, D. Q. Molecules 2013, 18, 14519.
(e) Liu, H.; Zou, Y.; Hu, Y.; Shi, D. Q. J. Heterocycl. Chem. 2011, 48, 877.
(f) Shi, D. Q.; Zou, Y.; Hu, Y.; Wu, H. J. Heterocycl. Chem. 2011, 48, 896.

Outlines

/