Citation: Sajjad Salahi, Malek Taher Maghsoodlou, Nourallah Hazeri, Mojtaba Lashkari, Santiago Garcia-Granda, Laura Torre-Fernandez. An efficient green synthesis of dispirohydroquinolines via a diastereoselective one-pot eight-component reaction[J]. Chinese Journal of Catalysis, ;2015, 36(7): 1023-1028. doi: 10.1016/S1872-2067(15)60846-4 shu

An efficient green synthesis of dispirohydroquinolines via a diastereoselective one-pot eight-component reaction

1.
a Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran;

Corresponding author: Malek Taher Maghsoodlou,
Received Date: 25 January 2015
Available Online: 19 March 2015

The one-pot eight-component reaction between Meldrum's acid, an aromatic aldehyde, and an aryl amine was achieved in the presence of citric acid catalyst. The corresponding dispirohydroquinolines were obtained in good yields with excellent diastereoselectivity. This method is a combination of the Knoevenagel and Michael reactions.
- Eight-component reaction,
- Dispirohydroquinoline,
- Meldrum's acid,
- Citric acid
1. [1]
  [1] Kumar A, Gupta G, Srivastava S. Green Chem, 2011, 13: 2459
2. [2]
  [2] Kumar A, Gupta M K, Kumar M. Green Chem, 2012, 14: 290
3. [3]
  [3] Tanaka K, Sugino T, Toda F. Green Chem, 2000, 2: 303
4. [4]
  [4] Raston C L, Scott J L. Green Chem, 2000, 2: 49
5. [5]
  [5] Anastas P T, Warner J C. Green Chemistry: Theory and Practice. Oxford: Oxford University Press, 1998
6. [6]
  [6] McNulty J, Das P. Eur J Org Chem, 2009: 4031
7. [7]
  [7] McNulty J, Das P. Tetrahedron Lett, 2009, 50: 5737
8. [8]
  [8] McNulty J, Das P, McLeod D. Chem Eur J, 2010, 16: 6756
9. [9]
  [9] Das P, McLeod D, McNulty J. Tetrahedron Lett, 2011, 52: 199
10. [10]
  [10] Dömling A. Chem Rev, 2006, 106: 17
11. [11]
  [11] Zhu J P, Bienayme H. Multicomponent Reactions. Weinheim: Wiley-VCH, 2005
12. [12]
  [12] Ramon D J, Yus M. Angew Chem Int Ed, 2005, 44: 1602
13. [13]
  [13] Dömling A, Wang W, Wang K. Chem Rev, 2012, 112: 3083
14. [14]
  [14] de Graaff C, Ruijter E, Orru R V A. Chem Soc Rev, 2012, 41: 3969
15. [15]
  [15] Duque M M S, Allais C, Isambert N, Constantieux T, Rodriguez J. Top Heterocycl Chem, 2010, 23: 227
16. [16]
  [16] Toure B B, Hall D G. Chem Rev, 2009, 109: 4439
17. [17]
  [17] Clarke P A, Santos S, Martin W H C. Green Chem, 2007, 9: 438
18. [18]
  [18] Pozharskii A F, Soldatenkov A T, Katritzky A R. Heterocycles in Life and Society. 2nd ed. New York: Wiley & Sons, 2011
19. [19]
  [19] Sajadikhah S S, Maghsoodlou M T, Hazeri N, Habibi-Khorassani S M, Shams-Najafi S J. Monatsh Chem, 2012, 143: 939
20. [20]
  [20] Marandi G, Hazeri N, Maghsoodlou M T, Habibi-Khorassani S M, Torbati N A, Rostami-Charati F, Skelton B W, Makhad M. J Heterocyclic Chem, 2013, 50: 568
21. [21]
  [21] Sajadikhah S S, Maghsoodlou M T, Hazeri N. Chin Chem Lett, 2014, 25: 58
22. [22]
  [22] Marandi G, Maghsoodlou M T, Hazeri N, Habibi-Khorassani S M, Torbati N A, Rostami-Charati F, Skelton B W, Makha M. Mol Divers, 2011, 15: 197
23. [23]
  [23] Salahi S, Hazeri N, Maghsoodlou M T, García-Granda S, Torre-Fernández L. J Chem Res, 2014, 38: 383
24. [24]
  [24] Lashkari M, Maghsoodlou M T, Hazeri N, Habibi-Khorassani S M, Akbarzadeh-Torbati N, García-Granda S, Torre-Fernández L. J Heterocyclic Chem, 2013, doi: 10.1002/jhet.1984
25. [25]
  [25] Hazeri N, Lashkari M, García-Granda S, Torre-Fernández L. Aust J Chem, 2014, 67: 1656
26. [26]
  [26] Wang P Y, Song L P, Yi H, Zhang M, Zhu S Z, Deng H M, Shao M. Tetrahedron Lett, 2010, 51: 3975
27. [27]
  [27] Ramachary D B, Chowdari N S, Barbas C F III. Angew Chem Int Ed, 2003, 42: 4233
28. [28]
  [28] Ramachary D B, Anebouselvy K, Chowdari N S, Barbas C F III. J Org Chem, 2004, 69: 5838
29. [29]
  [29] Ramachary D B, Chowdari N S, Barbas C F III. Synlett, 2003: 1910
30. [30]
  [30] Jiang B, Hao W J, Zhang J P, Tu S J, Shi F. Org Biomol Chem, 2009, 7: 2195
31. [31]
  [31] Shults E E, Semenova E A, Johnson A A, Bondarenko S P, Bagryanskaya I Y, Gatilov Y V, Tolstikov G A, Pommier Y. Bioorg Med Chem Lett, 2007, 17: 1362
32. [32]
  [32] Shi J, Liu Y B, Wang M, Lin L L, Liu X H, Feng X M. Tetrahedron, 2011, 67: 1781
33. [33]
  [33] Pizzirani D, Roberti M, Recanatini M. Tetrahedron Lett, 2007, 48: 7120
34. [34]
  [34] Hao W J, Jiang B, Tu S J, Wu S S, Han Z G, Cao X D, Zhang X H, Yan S, Shi F. J Comb Chem, 2009, 11: 310
35. [35]
  [35] Pizzirani D, Roberti M, Grimaudo S, Di Cristina A, Pipitone R M, Tolomeo M, Recanatini M. J Med Chem, 2009, 52: 6936
36. [36]
  [36] Tu S J, Zhu X T, Zhang J P, Xu J N, Zhang Y, Wang Q, Jia R H, Jiang B, Zhang J Y, Yao C S. Bioorg Med Chem Lett, 2006, 16: 2925
37. [37]
  [37] Wang X S, Zhang M M, Jiang H, Yao C S, Tu S J. Tetrahedron, 2007, 63: 4439
38. [38]
  [38] Sun J, Xia E Y, Wu Q, Yan C G. ACS Comb Sci, 2011, 13: 421
39. [39]
  [39] Ramachary D B, Barbas C F III. Chem Eur J, 2004, 10: 5323 Dumas A M, Seed A, Zorzitto A K, Fillion E. Tetrahedron Lett, 2007, 48: 7072
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沈阳化工大学材料科学与工程学院沈阳 110142