Citation: Zhao Yu, Tang Bo, Liu Xinlei, Li Wanzhen, Huang Mingyi, Wang Ming'an. Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 975-986. doi: 10.6023/cjoc201611013 shu

Regioselective Preparation of Enaminone via Enol Methyl Ether of 3-Acetyl-2-butenolide and Different Amines

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Corresponding author: Wang Ming'an, wangma@cau.edu.cn
Received Date: 10 November 2016
Revised Date: 14 December 2016

Fund Project: the National Natural Science Foundation of China 21172254the National Key Technologies R & D Program of China 2011BAE06B04

Figures(6)

The regioselective addition-elimination of 3-acetyl-4-methoxy-2-butenolide and 3-(1-methoxy ethylidene) furan-2, 4-dione having enol ether with different amines yielded novel stable enaminone derivatives in ethanol solution. Their structures were elucidated by ¹H NMR, ¹³C NMR, HRMS and X-ray diffraction data. Among of them, the Z/E isomers were observed for 3-(1-aminoethylidene)-furan-2, 4-dione. The structures of byproducts for preparing intermediates and title compounds were also characterized.
- 3-acetyl-4-methoxy-2-butenolide,
- 3-(1-methoxyethylidene)-furan-2, 4-dione,
- addition-elimination,
- enaminone
1. [1]
  Travert, N.; Al Mourabit, A. J. Am. Chem. Soc. 2004, 126, 10252. doi: 10.1021/ja047574e
2. [2]
  Paola. V.; Athina, G.; Kitka, A.; Matteo, I.; Franca, Z. Bioorg. Med. Chem. 2006, 14, 3859. doi: 10.1016/j.bmc.2006.01.043
3. [3]
  Patel, J. B.; Desai, V. A. Int. J. Drug Desi. Discovery 2011, 2, 393.
4. [4]
  Miqdad, O. A.; Abunada, N. M.; Hassaneen, H. M.; Abu Samaha, A. M. Int. J. Chem. 2011, 3, 20.
5. [5]
  (a) Nauen, R.; Jeschke, P.; Velten, R.; Beck, M. E.; Ebbinghaus-Kintscher, U.; Thielert, W.; Wolfel, K.; Haas, M.; Kunz, K.; Raupach, G. Pest Manage. Sci. 2015, 71, 850.
  (b) Jeanmart, S.; Edmunds, A. J. F.; Lamberth, C.; Pouliot, M. Bioorg. Med. Chem., 2016, 24, 317.
6. [6]
  (a) Leite, L.; Jansone, D.; Veveris, M.; Cirule, H.; Popelis, J.; Melikyan, G.; Avetisyan, A.; Lukevics, E. Eur. J. Med. Chem. 1999, 34, 859.
  (b) Melikyan, G. S.; Hovhannisyan, A. A.; Hayotsyan, S. S. Synth. Commun. 2012, 42, 2267.
7. [7]
  Lei, J. P.; Han, J. T.; Xu, Z. H.; Dong, H. B.; Wang, M. A. Chin. J. Org. Chem. 2012, 32, 1993 (in Chinese).
8. [8]
  Lei, J. P.; Dong, H. B.; Tang, B.; Wang, M. A. Chin. J. Pestc. Sci. 2012, 14, 669 (in Chinese). doi: 10.3969/j.issn.1008-7303.2012.06.14
9. [9]
  Tang, B.; Yang, M. Y.; Zhao, Y.; Kong, L. Q.; Wang, W. W.; Wang, M. A. Molecules 2015, 20, 13740. doi: 10.3390/molecules200813740
10. [10]
  Lacey, R. N. J. Chem. Soc., 1954, 832.
11. [11]
  Harras, M.; Bauer, T.; Kempe, R.; Schobert, R. Tetrahedron 2013, 69, 3677. doi: 10.1016/j.tet.2013.03.004
12. [12]
  Zimmer, H.; Amer, A.; Pham, C. V.; Schmidt, D. G. J. Org. Chem. 1988, 53, 3368. doi: 10.1021/jo00249a049
13. [13]
  (a) Eflenberger, V. F.; Klenk, H.; Reid, P. L. Angew. Chem. 1973, 85, 819.
  (b) Jackson, L. B.; Waring, A. J. J. Chem. Soc., Perkin Trans. 1 1988, 1791.
  (c) Jackson, L. B.; Waring, A. J. J. Chem. Soc., Perkin Trans. 2 1990, 1893.
  (d) Martin, R.; Lafrance, J. R.; Demerseman, P. Bull. Soc. Chim. Belg. 1991, 100, 539.
14. [14]
  Jung, M. E.; Street, L. J. J. Am. Chem. Soc. 1984, 106, 8327. doi: 10.1021/ja00338a071
15. [15]
  Porter, N. A.; Carter, R. L.; Mero, C. L.; Roepel, M. G.; Curran, D. P. Tetrahedron 1996, 52, 4181. doi: 10.1016/0040-4020(96)00077-4
16. [16]
  (a) Tietze, O.; Schiefner, B.; Ziemer, B.; Zschunke, A. Fresenius' J. Anal. Chem. 1997, 357, 477.
  (b) Hu, Y.; Wang, J. J.; Lu, A. M.; Yang, C. L. Bioorg. Med. Chem. Lett. 2014, 24, 3772.
  (c) Zhang, L. Z.; Ren, Z. J.; Lu, A. M.; Zhao, Z.; Xu, W. Q.; Bao, Q. Q.; Ding, W. J.; Yang, C. L. Chem. Res. Chin. Univ. 2015, 31, 228.
17. [17]
  Qu, Y. P.; Wang, L. X., Zhou, X. Y.; Feng, X. J.; Bao, M. Chin. J. Org. Chem. 2013, 33, 860 (in Chinese).
18. [18]
  (a) Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433.
  (b) Elassar, A-Z. A.; El-Khair, A. A. Tetrahedron 2003, 59, 8463.
19. [19]
  El-Apasery, M. A.; Al-Mousawi, S. M.; Mahmoud, H.; Elnagdi, M. H. Int. Res. J. Pure Appl. Chem. 2011, 1, 69. doi: 10.9734/IRJPAC
20. [20]
  Al-Mousawi, S. M.; El-Apasery, M. A.; Mahmoud, H.; Elnagdi, M. H. Int. Res. J. Pure Appl. Chem. 2012, 2, 77. doi: 10.9734/IRJPAC
21. [21]
  Martinez, J. C. G.; Duchowicz, P. R.; Estrada, M. R.; Zamarbide, G. N.; Castro, E. QSAR Comb. Sci. 2009, 28, 1376. doi: 10.1002/qsar.v28:11/12
22. [22]
  Liu, Y. X.; Zhao, H. P.; Wang, Z. W.; Li, Y. H.; Song, H. B.; Riches, H.; Beattie, D.; Gu, Y. C.; Wang, Q. M. Mol. Diversity 2013, 17, 701. doi: 10.1007/s11030-013-9466-6
23. [23]
  Zeng, R. J.; Sheng, H. T.; Rao, B.; Feng, Y.; Wang, H.; Sun, Y. H.; Chen, M.; Zhu, M. Z. Chem. Res. Chin. Univ. 2015, 31, 212. doi: 10.1007/s40242-015-4388-8
24. [24]
25. [25]
  Wei, Z. Z.; Xiao, L.; Wang, Y. Q.; Li, P. H. Chin. J. Org. Chem. 2014, 34, 985 (in Chinese).
26. [26]
  Shandala, M. Y.; Ayoub, M. T.; Mohammad, M. J. J. Heterocycl. Chem. 1984, 21, 1753. doi: 10.1002/jhet.v21:6
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