Reviews

Development of Domino Reactions with β-Enamino Esters as Key Intermediates

  • Han Ying ,
  • Sun Jing ,
  • Sun Yan ,
  • Gao Hong ,
  • Yan Chaoguo
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  • College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002

Received date: 2012-06-08

  Revised date: 2012-07-17

  Online published: 2012-07-12

Supported by

Project supported by the National Natural Science Foundation of China (Nos.20972132, 21172189)

Abstract

Domino reactions have attracted much high attention in recent years due to its convergence, productivity, facile execution and generation of highly diverse and complex products from easily available starting materials in a single operation. Addition of primary amines to electron-deficient alkynes could generated reactive enaminone (ester) in mild conditions, which have shown versatile reactivity and have been widely used in domino procedure as key reactive intermediate to develop a number of carbon-carbon bond formation reactions, heterocyclic and spiro cyclic constructions. In this paper the recent developments of the domino reactions with enamino esters as key intermediates based on our experimental investigation are reviewed.

Cite this article

Han Ying , Sun Jing , Sun Yan , Gao Hong , Yan Chaoguo . Development of Domino Reactions with β-Enamino Esters as Key Intermediates[J]. Chinese Journal of Organic Chemistry, 2012 , 32(9) : 1577 -1586 . DOI: 10.6023/cjoc201206008

References

[1] (a) Huisgen, R.; Morikawa, M.; Herbig, K.; Brunn, E. Chem. Ber. 1967, 100, 1094.   

(b) Huisgen, R. Z. Chem. 1968, 8, 290.

[2] Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekanth, A. R.; Mathen, J. S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.   

[3] Nair, V.; Menon, R. S.; Sreekanth, A.; Abhilash, N.; Biju, A. T. Acc. Chem. Res. 2006, 39, 520.   

[4] Yavari, I.; Mirzaei, A.; Moradi, L.; Khalili, G. Tetrahedron Lett. 2010, 51, 396.   

[5] Tejedor, D.; L髉ez-Tosco, S.; Cruz-Acosta, F.; M閚dez-Abt, G.; Garc韆-Tellado, F. Angew. Chem., Int. Ed. 2009, 48, 2090.   

[6] Dai, L. Z.; Qi, M. J.; Shi, Y. L.; Liu, X. G.; Shi, M. Org. Lett. 2007, 9, 3191.   

[7] Wang, Y. G.; Cui, S. L.; Lin, X. F. Org. Lett. 2006, 8, 1241.   

[8] (a) Cho, C. S. Tetrahedron Lett. 2005, 46, 1415.   

(b) Ziyaei-Halimehjani, A.; Saidi, M. R. Tetrahedron Lett. 2008, 49, 1244.   

[9] Zhu, Q. H.; Jiang, H. F.; Li, J. H.; Zhang, M.; Wang, X. J.; Qi, C. R. Tetrahedron 2009, 65, 4604.   

[10] (a) Lue, P.; Greenhill, J. V. Adv. Heterocycl. Chem. 1997, 67, 215.

(b) Elassara, A. Z.; El-Khair, A. A. Tetrahedron 2003, 59, 8463.   

[11] (a) Katritzky, A. R.; Hayden, A. E.; Kirichenko, K.; Pelphrey, P.; Ji, Y. J. Org. Chem. 2004, 69, 5108.  

(b) Sirijindalert, H.; Hansuthirakul, K.; Rashatasakhon, P.; Sukwattanasinitt, M.; Ajavakom, A. Tetrahedron 2010, 66, 5161.   

[12] (a) Vohra, R. K.; Bruneau, C.; Renaud, J. Adv. Synth. Catal. 2006, 348, 2571.  

(b) Kumar, A.; Maurya, R. A. Tetrahedron 2008, 64, 3477.   

[13] (a) Arcadi, A.; Bianchi, G.; Di Giuseppe, S.; Marinelli, F. Green Chem. 2003, 64.  

(b) Khosropour, A. R.; Khodaei, M. M.; Kookhazadeh, M. Tetrahedron Lett. 2004, 45, 1725.   

[14] (a) Liu, W. B.; Jiang, H. F.; Huang, L. B. Org. Lett. 2010, 12, 312.  

(b) Liu, W. B.; Jiang, H. F.; Zhang, M.; Qi, C. R. J. Org. Chem. 2010, 75, 966.  

(c) Bayat, M.; Imanieh, H.; Hassanzadeh, F. Tetrahedron Lett. 2010, 51, 1873.  

(d) Terzidis, M. A.; Stephanidou-Stephanatou, J.; Tsoleridis, C. A.; Terzis, A.; Raptopoulou, C. P.; Psycharis, V. Tetrahedron 2010, 66, 947.   

[15] (a) Yavari, I.; Mirzaei, A.; Moradi, L.; Khalili, G. Tetrahedron Lett. 2010, 51, 396.  

(b) Yavari, I.; Seyfi, S.; Hossaini, Z. Tetrahedron Lett. 2010, 51, 2193.  

(c) Kumaraswamy, G.; Rambabu, D.; Jayaprakash, N.; Rao, G. V.; Sridhar, B. Eur. J. Org. Chem. 2009, 4158.   

[16] (a) Alizadeh, A.; Rostamnia, S.; Hu, M. L. Synlett 2006, 1592.

(b) Adib, M.; Mohammadi, B.; Mahdavi, M.; Abbasi, A.; Kesheh, M. R. Synlett 2007, 2497.

(c) Alizadeh, A.; Rostamnia, S.; Zhu, L. G. Tetrahedron Lett. 2010, 51, 4750.  

(d) Teimouri, M. B.; Abbasi, T. Tetrahedron 2010, 66, 3795.   

[17] (a) Kielland, N.; Lavilla, R. Top. Heterocycl. Chem. 2010, 25, 127.  

(b) Shaabani, A.; Rezayan, A. H.; Sarvary, A. Mol. Divers. 2011, 15, 41.   

[18] Sun, J.; Xia, E. Y.; Wu, Q.; Yan, C. G. Org. Lett. 2010, 12, 3678.   

[19] Yamuna, E.; Zeller, M.; Prasad, K. J. R. Tetrahedron Lett. 2011, 52, 6805.   

[20] Lei, M.; Zhan, Z. J.; Tian, W.; Lu, P. Tetrahedron 2012, 68, 3361.   

[21] Zhang, M.; Jiang, H. F.; Liu, H. L.; Zhu, Q. H. Org. Lett. 2007, 9, 4111

[22] Sun, J.; Xia, E. Y.; Wu, Q.; Yan, C. G. ACS Comb. Sci. 2011, 13, 421.   

[23] Sun, J.; Wu, Q.; Xia, E. Y.; Yan, C. G. Eur. J. Org. Chem. 2011, 2981.   

[24] Sun, J.; Sun, Y.; Gao, H.; Yan, C. G. Eur. J. Org. Chem. 2012, 1976.

[25] Sun. J.; Wu, Q.; Zhang, L. J.; Yan, C. G. Chin. J. Chem. 2012, 30, 1548.   

[26] Kiruthika, S. E.; Lakshmi, N. V.; Banu, B. R.; Perumal, P. T. Tetrahedron Lett. 2011, 52, 6508.   

[27] Sun, Y.; Sun, J.; Yan, C. G. Tetrahedron Lett. 2012, 53, 3647.   

[28] Alizadeh, A.; Rezvanian, A.; Zhu, L. G. J. Org. Chem. 2012, 77, 4385.   

[29] Sun, J.; Sun, Y.; Gao, H.; Yan, C. G. Eur. J. Org. Chem. 2011, 6952.   

[30] Zhu, Q.; Jiang, H. F.; Li, J.; Liu, S.; Xia, C.; Zhang, M. J. Comb. Chem. 2009, 11, 685.   

[31] Khan, A. T.; Ghosh, A.; Khan, A. M. Tetrahedron Lett. 2012, 53, 2622.   

[32] Liu, W. B.; Jiang, H. F.; Huang, L. B. Org. Lett. 2010, 12, 312.   

[33] Das, B.; Chinna Reddy, G.; Balasubramanyam, P.; Aneyulu, V. Synthesis 2010, 1625.

[34] Nagarapu, L.; Mallepalli, R.; Yeramanchi, L.; Bantu, R. Tetrahedron Lett. 2011, 52, 3401.   

[35] Ghabraie, E.; Balalaie, S.; Bararjanian, M.; Bijanzadeh, H. R.; Rominger, F. Tetrahedron 2011, 67, 5415.   

[36] Yavari, I.; Bayat, M. J.; Sirouspour, M.; Souri, S. Tetrahedron 2010, 66, 7995.   

[37] Yavari, I.; Bayat, M. J. Tetrahedron Lett. 2011, 52, 6649.   

[38] Samai, S.; Nandi, G. C.; Chowdhury, S.; Singh, M. S. Tetrahedron 2011, 67, 5935.   

[39] Khan, A. T.; Khan, M. M. Tetrahedron Lett. 2011, 52, 3455.  

[40] Teimouri, M. B.; Abbasi, T. Tetrahedron 2010, 66, 3795.  

[41] Ramesh, K.; Murthy, S. N.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 2362.   

[42] Yin, G. W.; Zhu, Y. X.; Lu, P.; Wang, Y. G. J. Org. Chem. 2011, 76, 8922.   

[43] Tu, X. C.; Feng, H.; Tu, M S.; Jiang, B.; Wang, S. L.; Tu, S. J. Tetrahedron Lett. 2012, 53, 3169.   

[44] Zohreh, N.; Alizadeh, A. Tetrahedron 2011, 67, 4595.   

[45] Alizadeh, A.; Zarei, A.; Alizadeh, A. R. A.; Zarei, A.; Rezvanian, A. Helv. Chim. Acta 2012, 95, 278.  

[46] Sirijindalert, T.; Hansuthirakul, K.; Rashatasakhon, P.; Sukwattanasinitt, M.; Ajavakom, A. Tetrahedron Lett. 2011, 52, 5789.   

[47] Sun, J.; Sun, Y.; Xia, E. Y.; Yan, C. G. ACS Comb. Sci. 2011, 13, 436.   

[48] Kikuchi, S.; Iwai, M.; Murayama, H.; Fukuzawa, S. Tetrahedron Lett. 2008, 49, 114.   

[49] Sun, J.; Sun, Y.; Gao, H.; Yan, C. G. Synthesis 2012, 1069.

[50] Sun, Y.; Sun, J.; Yan, C. G. Mol. Divers. 2012, 16, 163.   

[51] Teimouri, M. B.; Abbasi, T.; Mivehchi, H. Tetrahedron 2008, 64, 10425.  

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