Citation: Asha V. Chate, Umesh B. Rathod, Jagdish S. Kshirsagar, Pradip A. Gaikwad, Kishor D. Mane, Pravin S. Mahajan, Mukesh D. Nikam, Charansingh H. Gill. Ultrasound assisted multicomponent reactions: A green method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular reusable catalyst in water[J]. Chinese Journal of Catalysis, ;2016, 37(1): 146-152. doi: 10.1016/S1872-2067(15)61005-1 shu

Ultrasound assisted multicomponent reactions: A green method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular reusable catalyst in water

1.
Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University, Aurangabad 431004, India

Corresponding author: Charansingh H. Gill,
Received Date: 19 September 2015
Available Online: 25 October 2015

We demonstrate a superficial method for the synthesis of N-substituted 1,8-dioxo-decahydroacridines using β-cyclodextrin as a supramolecular, biodegradable, and reusable catalyst in aqueous medium. The reaction product is in excellent yield with moderate to excellent selectivity. The mechanistic transformation presumably proceeds via a one-pot, multicomponent cyclization of dimedone in the presence of aromatic aldehydes and aromatic amines/INH, undergoing a tandem Michael addition reaction. The proposed approach in this study provides a highly efficient and environmentally benign route to N-substituted 1,8-dioxo-decahydroacridines.
- Tandem reaction,
- N-Substituted 1,8-dioxo-decahydroacridines,
- β-Cyclodextrin,
- Supramolecular catalysis,
- Water
1. [1]
  [1] J. Szejtli, Chem. Rev., 1998, 98, 1743.
2. [2]
  [2] H. Dodziuk, Cyclodextrins and Their Complexes, Chemistry, Analytical Methods, Applications, Wiley-VCH, Weinheim, 2006.
3. [3]
  [3] E. M. M. Del Valle, Process Biochem., 2004, 39, 1033.
4. [4]
  [4] M. E. Davis, M. E. Brewster, Nat. Rev. Drug Disc., 2004, 3, 1023.
5. [5]
  [5] A. L. Laza-Knoerr, R. Gref, P. Couvreur, J. Drug Target., 2010, 18, 645.
6. [6]
  [6] H. B. Ji, D. P. Shi, M. Shao, Z. Li, L. F. Wang, Tetrahedron Lett., 2005, 46, 2517.
7. [7]
  [7] A. Dömling, I. Ugi, Angew. Chem. Int. Ed., 2000, 39, 3168.
8. [8]
  [8] A. Dömling, Chem. Rev., 2006, 106, 17.
9. [9]
  [9] J. P. Zhu, H. Bienaymé, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
10. [10]
  [10] R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res., 1996, 19, 123.
11. [11]
  [11] S. Girault, P. Grellier, A. Berecibar, L. Maes, E. Mouray, P. Lemiere, M. A. Debreu, E. Davioud-Charvet, C. Sergheraet, J. Med. Chem., 2000, 43, 2646.
12. [12]
  [12] Y. Mikata, M. Yokoyama, K. Mogami, M. Kato, I. Okura, M. Chikira, S. Yano, Inorg. Chim. Acta, 1998, 279, 51.
13. [13]
  [13] S. A. Gamega, J. A. Spicer, G. J. Atwell, G. J. Finlay, B. C. Baguley, W. A. Deny, J. Med. Chem., 1999, 42, 2383.
14. [14]
  [14] M. Wainwright, J. Antimicrob. Chemother., 2001, 47, 1.
15. [15]
  [15] I. Antonini, P. Polucci, L. R. Kelland, E. Menta, N. Pescalli, S. Martelli, J. Med. Chem., 1999, 42, 2535.
16. [16]
  [16] S. Gallo, S. Atifi, A. Mohamoud, C. Santelli-Rouvier, K. Wolfart, J. Molnar, J. Barbe, Eur. J. Med. Chem., 2003, 38, 19.
17. [17]
  [17] L. Ngadi, A. M. Galy, J. P. Galy, J. Barbe, A. Cremieux, J. Chevalier, D. Sharples, Eur. J. Med. Chem., 1990, 25, 67.
18. [18]
  [18] F. Bossert, W. Vater, Med. Res. Rev., 1989, 9, 291.
19. [19]
  [19] O. Berkan, B. Sarac, R. Simsek, S. Yildirim, Y. Sariogli, C. Safak, Eur. J. Med. Chem., 2002, 37, 519.
20. [20]
  [20] P. Murugan, P. Shanmugasundaram, V. T. Ramakrishnan, B. Venkatachalapathy, N. Srividya, P. Ramamurthy, K. Gunasekaran, D. Velmurugan, J. Chem. Soc., Perkin Trans. 2, 1998, 999.
21. [21]
  [21] A. Islam, P. Murugan, K. C. Hwang, C. H. Cheng, Synth. Metal, 2003, 139, 347.
22. [22]
  [22] S. J. Tu, C. B. Miao, Y. Gao, F. Fang, Q. Y. Zhuang, Y. J. Feng, D. Q. Shi, Synlett, 2004, 255.
23. [23]
  [23] A. A. Bakibaev, V. D. Fillimonov, E. S. Nevgodova, Zh. Org. Khim., 1991, 27, 1519.
24. [24]
  [24] S. J. Tu, F. Fang, S. L. Zhu, T. J. Li, X. J. Zhang, Q. Y. Zhuang, J. Heterocycl. Chem., 2004, 41, 767.
25. [25]
  [25] M. Suarez, A. Loupy, E. Salfran, L. Moran, E. Rolando, Heterocycles, 1999, 51, 21.
26. [26]
  [26] S. J. Tu, Z. S. Lu, D. Q. Shi, C. S. Yao, Y. Gao, C. Guo, Synth. Commun., 2002, 32, 2181.
27. [27]
  [27] N. Martin, M. Quinteiro, C. Seoane, J. L. Soto, A. Mora, M. Suarez, E. Ochoa, A. Morales, J. R. del Bosque, J. Heterocycl. Chem., 1995, 32, 235.
28. [28]
  [28] B. Das, P. Thirupathi, I. Mahender, V. S. Reddy, Y. K. Rao, J. Mol. Catal. A, 2006, 247, 233.
29. [29]
  [29] X. S. Wang, D. Q. Shi, D. Q. Zhang, Y. F. Wang, S. J. Tu, Chin. J. Org. Chem., 2004, 24, 430.
30. [30]
  [30] S. J. Tu, C. B. Miao, Y. A. Gao, Y. J. Feng, J. C. Feng, Chin. J. Org. Chem., 2002, 20, 703.
31. [31]
  [31] X. S. Wang, D. Q. Shi, S. H. Wang, S. J. Tu, Chin. J. Org. Chem., 2003, 23, 1291.
32. [32]
  [32] Y. L. Li, M. M. Zhang, X. S. Wang, D. Q. Shi, S. J. Tu, X. Y. Wei, Z. M. Zong, J. Chem. Res., 2005, 600.
33. [33]
  [33] X. S. Wang, M. M. Zhang, H. Jiang, D. Q. Shi, S. J. Tu, X. Y. Wei, Z. M. Zong, Synthesis, 2006, 4187.
34. [34]
  [34] T. S. Jin, J. S. Zhang, T. T. Guo, A. Q. Wang, T. S. Li, Synthesis, 2004, 2001.
35. [35]
  [35] S. Balalaie, F. Chadegan, F. Darviche, H. R. Bijanzadeh, Chin. J. Chem., 2009, 27, 1953.
36. [36]
  [36] K. Venkatesan, S. S. Pujari, K. V. Srinivasan, Synth. Commun., 2009, 39, 228.
37. [37]
  [37] M. Kidwai, D. Bhatnagar, Tetrahedron Lett., 2010, 51, 2700.
38. [38]
  [38] M. V. Seyed, K. Samad, A. B. Maryam Saeed, Arab. J. Chem., 2014, doi,101016/jarabjc201410026.
39. [39]
  [39] G. Zbancioc, O. Florea, P. G. Jones, I. I. Mangalagiu, Ultrason. Sonochem., 2012, 19, 399.
40. [40]
  [40] J. P. Hallett, T. Welton, Chem. Rev., 2011, 111, 3508.
41. [41]
  [41] P. A. Grieco, Organic Synthesis in Water. Blackie, Springer, 1998.
42. [42]
  [42] R. Breslow, Acc. Chem. Res., 2004, 37, 471.
43. [43]
  [43] N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, M. R. Saidi, J. Org. Chem., 2006, 71, 3634.
44. [44]
  [44] S. Tiwari, A. Kumar, Angew. Chem. Int. Ed., 2006, 45, 4824.
45. [45]
  [45] Y. Jung, R. A. Marcus, J. Am. Chem. Soc., 2007, 129, 5492.
46. [46]
  [46] K. A. Connors, Chem. Rev., 1997, 97, 1325.
47. [47]
  [47] M. V. Rekharsky, Y. Inoue, Chem. Rev., 1998, 98, 1875.
48. [48]
  [48] J. L. Song, Z. F. Zhang, B. X. Han, S. Q. Hu, W. J. Li, Y. Xie, Green Chem., 2008, 10, 1337.
49. [49]
  [49] K. Takahashi, Chem. Rev., 1998, 98, 2013.
50. [50]
  [50] S. S. Hu, J. Y. Li, J. F. Xiang, J. Pan, S. Z. Luo, J. P. Cheng, J. Am. Chem. Soc., 2010, 132, 7216.
51. [51]
  [51] C. F. Ke, C. Yang, T. Mori, T. Wada, Y. Liu, Y. Inoue, Angew. Chem. Int. Ed., 2009, 48, 6675.
52. [52]
  [52] K. Kanagaraj, K. Pitchumani, J. Org. Chem., 2013, 78, 744.
53. [53]
  [53] S. N. Murthy, B. Madhav, V. P. Reddy, Y. V. D. Nageswar, Tetrahedron Lett., 2010, 51, 3649.
54. [54]
  [54] G. Cafeo, F. H. Kohnke, L. Valenti, Tetrahedron Lett., 2009, 50, 4138.
55. [55]
  [55] W. K. Chan, W. Y. Yu, C. M. Che, M. K. Wong, J. Org. Chem., 2003, 68, 6576.
56. [56]
  [56] C. Rousseau, B. Christensen, T. E. Petersenb, M. Bols, Org. Biomol. Chem., 2004, 2, 3476.
57. [57]
  [57] C. Rousseau, B. Christensen, M. Bols, Eur. J. Org. Chem., 2005, 2734.
58. [58]
  [58] T. H. Manjashetty, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett., 2011, 21, 2125.
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