SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2023 , Vol. 43 >Issue 2: 742 - 750

DOI: https://doi.org/10.6023/cjoc202207032

Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water

  • Wei Wang ,
  • Zheyu Zhang ,
  • Xue Zhang ,
  • Haifeng Yu ,
  • Hui Luo ,
  • Dongyue Huo ,
  • Yupeng Xu ,
  • Xiaobo Zhao
Expand
  • College of Chemistry, Baicheng Normal University, Baicheng, Jilin 137000
* Corresponding authors. E-mail: ;
.

Received date: 2022-07-25

  Revised date: 2022-08-23

  Online published: 2022-09-15

Supported by

Natural Science Foundation of Jilin Province(20210101128JC); Foundation of Jilin Provincial Department of Education(JJKH20200001KJ)

Fold

Abstract

For the first time, the aqueous [5C＋1N] annulation of α-alkenoyl ketene dithioacetals and amines for the synthesis of polysubstituted 2,3-dihydropyridin-4(1H)-ones was developed. In boiling water, [5C＋1N] annulation of (E)-2-(bis(ethyl- thio)methylene)-3-oxo-N,5-diarylpent-4-enamides 1 and organic amines 2 smoothly occurred, and polysubstituted 2,3-dihydropyridin-4(1H)-ones 3 was obtained in moderate yields.

Key words： aqueous reaction; ketene dithioacetals; amines; pyridinones

Cite this article

Wei Wang , Zheyu Zhang , Xue Zhang , Haifeng Yu , Hui Luo , Dongyue Huo , Yupeng Xu , Xiaobo Zhao . Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water[J]. Chinese Journal of Organic Chemistry, 2023 , 43(2) : 742 -750 . DOI: 10.6023/cjoc202207032

References

[1]
Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302.
[2]
Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415.
[3]
Kitanosono, T.; Masuda, K.; Xu, P. Y.; Kobayashi, S. Chem. Rev. 2018, 118, 679.
[4]
Song, H. X.; Han, Q. Y.; Zhao, C. L.; Zhang, C. P. Green Chem. 2018, 20, 1662.
[5]
Cao, T. T.; Zhang, W. K.; Qin, F. H.; Kang, Q. Q.; Dong, Y. R.; Li, Q.; Kang, C.; Wei, W. T. ACS Sustainable Chem. Eng. 2020, 8, 16946.
[6]
Sun, K.; Lv, Q. Y.; Chen, X. L.; Qu, L. B.; Yu, B. Green Chem. 2021, 23, 232.
[7]
Jiang, J.; Xiao, F.; He, W. M.; Wang, L. Y. Chin. Chem. Lett. 2021, 32, 1637.
[8]
Chattopadhyay, A. K.; Hanessian, S. Chem. Commun. 2015, 51, 16437.
[9]
Chattopadhyay, A. K.; Hanessian, S. Chem. Commun. 2015, 51, 16450.
[10]
Pepe, A.; Pamment, M.; Kim, Y. S.; Lee, S.; Lee, Mi. J.; Beebe, K.; Filikov, A.; Neckers, L.; Trepel, J. B.; Malhotra, S. V. J. Med. Chem. 2013, 56(21), 8280.
[11]
Eiden, C. G.; Aldrich, C. C. J. Org. Chem. 2017, 82, 7806.
[12]
Seki, H.; Georg, G. I. Synlett 2014, 25, 2536.
[13]
Kim, Y. W.; Georg, G. I. Org. Lett. 2014, 16, 1574.
[14]
Murphy, J. P.; Hadden, M.; Stevenson, P. J. Tetrahedron 1997, 53(34), 11827.
[15]
Igarashi, E.; Sakamoto, K.; Yoshimura, T.; Matsuo, J. I. Tetrahedron Lett. 2019, 60, 13.
[16]
Ma, D. W.; Sun, H. Y. Org. Lett. 2000, 2, 2503.
[17]
Leflemme, N.; Dallemagne, P.; Rault, S. Synthesis 2002, 12, 1740.
[18]
Yang, Y. RSC Adv. 2015, 5, 18894.
[19]
Yuan, Y.; Li, X.; Ding, K. L. Org. Lett. 2002, 4, 3309.
[20]
Pégot, B.; Vo-Thanh, G. Synlett 2005, 1409.
[21]
Lei, C. H.; Wang, D. X.; Zhao, L.; Zhu, J. P.; Wang, M. X. Chem.- Eur. J. 2013, 19, 16981.
[22]
Obydennov, D. L.; El-Tantawy, A. I.; Sosnovskikha, V. Y. J. Org. Chem. 2018, 83, 13776.
[23]
Svetlik, J.; Kettmanna, V.; Zaleska, B. Tetrahedron Lett. 2005, 46, 5511.
[24]
Elias, R. S.; Saeed, B. A.; Saour, K. Y.; Al-Masoudi, N. A. Tetrahedron Lett. 2008, 49, 3049.
[25]
MacDonald, F. K.; Burnell, D. J. J. Org. Chem. 2009, 74, 6973.
[26]
Ranade, A. R.; Georg, G. I. J. Org. Chem. 2014, 79, 984.
[27]
Niphakis, M. J.; Turunen, B. J.; Georg, G. I. J. Org. Chem. 2010, 75, 6793.
[28]
Gouault, N.; Roch, M. L.; Cheignon, A.; Uriac, P.; David, M. Org. Lett. 2011, 13, 437.
[29]
Trinh, T. T. H.; Nguyen, K. H.; Amaral, P. A.; Gouault, N. Beilstein J. Org. Chem. 2013, 9, 2042.
[30]
Pan, L.; Bi, X. H.; Liu, Q. Chem. Soc. Rev. 2013, 42, 1251.
[31]
Pan, L.; Liu, Q. Synlett 2011, 22, 1073.
[32]
Bi, X. H.; Dong, D. W.; Liu, Q.; Pan, W.; Zhao, L.; Li, B. J. Am. Chem. Soc. 2005, 127, 4578.
[33]
Zhang, L.; Liang, F. S.; Cheng, X.; Liu, Q. J. Org. Chem. 2009, 74, 899.
[34]
Zhao, X. B.; Wang, Y. M.; Yu, H. F.; Lv, Y. C.; Jiang, S. A.; Wang, N. Tetrahedron 2021, 97, 132427.
[35]
Dong, D. W.; Bi, X. H.; Liu, Q.; Cong, F. D. Chem. Commun. 2005, 3580.
[36]
Gui, Q. W.; Wang, B. B.; Zhu, S.; Li, F. L.; Zhu, M. X.; Yi, M.; Yu, J. L.; Wu, Z. L.; He, W. M. Green Chem. 2021, 23, 4430.
[37]
Wu, Y.; Chen, J. Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W. M. Green Chem. 2021, 23, 3950.
[38]
Gui, Q.W.; Teng, F.; Li, Z. C.; Xiong, Z. Y.; Jin, X. F.; Lin, Y. W.; Cao, Z.; He, W. M. Chin. Chem. Lett. 2021, 32, 1907.
[39]
Yu, H. F.; Liao, P. Q.; Mei, Z. M. Synthesis, 2021, 52, 2111.
[40]
Yu, H. F.; Wang, K. H.; Zhang, X.; Wang, W. J. Synthesis 2021, 53, 1989.
[41]
Yu, H. F.; Zhao, L. J.; Diao, Q. P.; Li, T. C.; Liao, P. Q.; Hou, D. Y.; Xin, G. Synlett 2017, 28, 1828.
[42]
Dong, D. W.; Ouyang, Y.; Yu, H. F.; Liu, Q.; Liu, J.; Wang, M.; Zhu, J. J. Org. Chem. 2005, 70, 4535.
[43]
Yu, H. F.; Liao, P. Q. Tetrahedron Lett. 2016, 57, 2868.
[44]
Qi, F.; Yu, H. F.; Wang, Y. N.; Lv, Y.; Li, Y. X.; Han, L.; Wang, R.; Feng, X. N. Synth. Commun. 2017, 47, 2220.
[45]
Hu, X. Y.; Yu, H. F.; Wang, W. J.; Jiang, S. A.; Liu, Q.; He, J. Chin. J. Org. Chem. 2019, 39, 3183. (in Chinese)
[45]
(胡小宇, 于海丰, 王文举, 姜思傲, 刘奇, 何洁, 有机化学, 2019, 39, 3183.)
[46]
Zhao, Y. H.; Yu, H. F.; Liao, P. Q.; Wang, W. J. Chem. Res. Chin. Univ. 2020, 36, 847.
[47]
Zhao, X. B.; Jiang, S. A.; Wang, N.; Yu, H. F. Synth. Commun. 2020, 50, 3404.
[48]
Jia, J.; Su, Y.; Yu, H. F.; Du, H. T.; Mei, Z. M. Synth. Commun. 2021, 51, 1581.
[49]
Yu, H. F.; Zhang, Z. Y.; Zhang, X.; Xu, Y. P.; Huo, D. Y.; Zhang, L. Y.; Wang, W. J. J. Org. Chem. 2022, 87, 2985.
[50]
CCDC 2163176 (3a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif
Options
Outlines

/

〈 〉