Citation: Nader Ghaffari Khaligh. Four-component one-pot synthesis of unsymmetrical polyhydroquinoline derivatives using 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as a catalyst[J]. Chinese Journal of Catalysis, ;2014, 35(7): 1036-1042. doi: 10.1016/S1872-2067(14)60038-3 shu

Four-component one-pot synthesis of unsymmetrical polyhydroquinoline derivatives using 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate as a catalyst

Nader Ghaffari Khaligh ^a,b,,

1.
a. Department of Chemistry, Qaemshahr Branch, Islamic Azad University, Qaemshahr, 47651-61964, Iran;

Corresponding author: Nader Ghaffari Khaligh,
Received Date: 12 December 2013
Available Online: 15 January 2014

3-Methyl-1-sulfonic acid imidazolium hydrogen sulfate has been used as an efficient, halogen-free, and reusable Brönsted acidic ionic liquid catalyst for the synthesis of ethyl-4-aryl/heteryl-hexahydro-trimehtyl-5-oxoquinoline-3-carboxylates via the one-pot condensation of dimedone with aryl/heteryl aldehydes, ethyl acetoacetate, and ammonium acetate under solvent-free conditions. This method has the advantage of being clean and simple, as well as providing the desired product in high yield over a short reaction time. Furthermore, the catalyst could be recycled and reused four times without any discernible reduction in activity.
- Unsymmetrical polyhydroquinoline,
- Brönsted acidic ionic liquid catalyst,
- Multicomponent reaction,
- Solvent-free condition
1. [1]
  [1] Brock E D, Lewis D M, Yousaf T I, Harper H H. WO Patent 9951688. 1999
2. [2]
  [2] Sakata G, Makino K, Karasawa Y. Heterocycles 1988, 27: 2481
3. [3]
  [3] Demeunynck M, Moucheron C, Mesmaeker A K D. Tetrahedron Lett, 2002, 43: 261
4. [4]
  [4] Ali M M, Tasneem T, Rajanna K C, Prakash P K S. Synlett, 2001: 251
5. [5]
  [5] Cho C S, Kim B T, Kim T J, Shim S C. Chem Commun, 2001: 2576
6. [6]
  [6] Crousse B, Begue J P, Bonnet-Delpon D. J Org Chem, 2000, 65: 5009
7. [7]
  [7] Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509
8. [8]
  [8] Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046
9. [9]
  [9] Sawada Y, Kayakiri H, Abe Y, Mizutani T, Inamura N, Asano M, Hatori C, Aramori I, Oku T, Tanaka H. J Med Chem, 2004, 47: 2853
10. [10]
  [10] Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193
11. [11]
  [11] Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224
12. [12]
  [12] Fokialakis N, Magiatis P, Chinou I, Mitaku S, Tillequin F. Chem Pharm Bull, 2002, 50: 413
13. [13]
  [13] Fossa P, Mosti L, Menozzi G, Marzano C, Baccichetti F, Bordin F. Bioorg Med Chem, 2002, 10: 743
14. [14]
  [14] Ryckebusch A, Deprez-Poulain R, Maes L, Debreu-Fontaine M A, Mouray E, Grellier P, Sergheraert C. J Med Chem, 2003, 46: 542
15. [15]
  [15] Morgan L R, Jursic B S, Hooper C L, Neumann D M, Thangaraj K, LeBlanc B. Bioorg Med Chem Lett, 2002, 12: 3407
16. [16]
  [16] Kouznetsov V V. Tetrahedron, 2009, 65: 2721
17. [17]
  [17] Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396
18. [18]
  [18] Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419
19. [19]
  [19] Mauzerall D, Westheimer F H. J Am Chem Soc, 1955, 77: 2261
20. [20]
  [20] Godfraind T, Miller R, Mibo M. Pharmacol Rev, 1986, 38: 321
21. [21]
  [21] Stout D M, Meyers A I. Chem Rev, 1982, 82: 223
22. [22]
  [22] Janis R A, Triggle D J. J Med Chem, 1983, 26: 775
23. [23]
  [23] Bossert F, Mayer H, Wehinger E. Angew Chem Int Ed, 1981, 20: 762
24. [24]
  [24] Toussaint C, De Pauw L, Vienne A, Gevenois P A, Quintin J, Gelin M, Pasteels J L. Am J Kidney Dis, 1993, 21: 54
25. [25]
  [25] Kawase M, Shah A, Gaveriya H, Motohashi N, Sakagami H, Varga A, Molnar J. Bioorg Med Chem, 2002, 10: 1051
26. [26]
  [26] Ladani N K, Mungra D C, Patel M P, Patel R G. Chin Chem Lett, 2011, 22: 1407
27. [27]
  [27] Wang S X, Li Z Y, Zhang J C, Li J T. Ultrason Sonochem, 2008, 15: 677
28. [28]
  [28] Wang L M, Sheng J, Zhang L, Han J W, Fan Z Y, Tian H, Qian C T. Tetrahedron, 2005, 61: 1539
29. [29]
  [29] Kumar A, Maurya R A. Tetrahedron, 2007, 63: 1946
30. [30]
  [30] Undale K A, Shaikh T S, Gaikwad D S, Pore D M. C R Chim, 2011, 14: 511
31. [31]
  [31] Ji S J, Jiang Z Q, Lu J, Loh T P. Synlett, 2004: 831
32. [32]
  [32] Maheswara M, Siddaiah V, Damu V G L, Rao C V. Arkivoc, 2006: 201
33. [33]
  [33] Sapkal S B, Shelke K F, Shingate B B, Shingare M S. Tetrahedron Lett, 2009, 50: 1754
34. [34]
  [34] Katkar S S, Mohite P H, Gadekar L S, Arbad B R, Lande M K. Green Chem Lett Rev, 2010, 3: 287
35. [35]
  [35] Safari J, Banitaba S H, Khalili S D. J Mol Catal A, 2011, 335: 46
36. [36]
  [36] Ko S, Sastry M N V, Lin C, Yao C F. Tetrahedron Lett, 2005, 46: 5771
37. [37]
  [37] Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615
38. [38]
  [38] Rogers R D, Seddon K R. Ionic Liquids: Industrial Application to Green Chemistry. Washington DC: Am Chem Soc, 2002
39. [39]
  [39] Miao C X, He L N, Wang J Q, Wang J L. Adv Synth Catal, 2009, 351: 2209
40. [40]
  [40] Cole A C, Jensen J L, Ntai I, Tran K L T, Weaver K J, Forbes D C, Davis J H Jr. J Am Chem Soc, 2002, 124: 5962
41. [41]
  [41] Arfan A, Bazureau J P. Org Process Res Dev, 2005, 9: 743
42. [42]
  [42] Wasserscheid P, Sesing M, Korth W. Green Chem, 2002, 4: 134
43. [43]
  [43] Wasserscheid P, van Hal R, Bösmann A. Green Chem, 2002, 4: 400
44. [44]
  [44] Fraga-Dubreuil J, Bourahla K, Rahmouni M, Bazureau J P, Hamelin J. Catal Commun, 2002, 3: 185
45. [45]
  [45] Gathergood N, Garcia M T, Scammells P J. Green Chem, 2004, 6: 166
46. [46]
  [46] Garcia M T, Gathergood N, Scammells P J. Green Chem, 2005, 7: 9
47. [47]
  [47] Gu Y L, Zhang J, Duan Z Y, Deng Y Q. Adv Synth Catal, 2005, 347: 512
48. [48]
  [48] Kalita P, Kumar R. Microporous Mesoporous Mater, 2012, 149: 1
49. [49]
  [49] Khaligh N G. J Mol Catal A, 2011, 349: 63
50. [50]
  [50] Khaligh N G. Catal Sci Technol, 2012, 2: 1633
51. [51]
  [51] Cave G W V, Raston C L, Scott J L. Chem Commun, 2001: 2159
52. [52]
  [52] Nagarapu L, Kumari M D, Kumari N V, Kantevari S. Catal Commun, 2007, 8: 1871
53. [53]
  [53] Saikia L, Dutta D, Dutta D K. Catal Commun, 2012, 19: 1
54. [54]
  [54] Baghbanian S M, Khaksar S, Mohammad-Vahdat S, Farhang M, Tajbakhsh M. Chin Chem Lett, 2010, 21: 563
55. [55]
  [55] Khojastehnezhad A, Moeinpour F, Davoodnia A. Chin Chem Lett, 2011, 22, 807
56. [56]
  [56] Khazaei A, Zolfigol M A, Moosavi-Zare A R, Afsar J, Zare A, Khakyzadeh V, Beyzavi M H. Chin J Catal (催化学报), 2013, 34: 1936
57. [57]
  [57] Heydari A, Khaksar S, Tajbakhsh M, Bijanzadeh H R. J Fluorine Chem, 2009, 130: 609
58. [58]
  [58] Hong M, Cai C, Yi W B. J Fluorine Chem, 2010, 131: 111
59. [59]
  [59] Surasani R, Kalita D, Rao A V D, Yarbagi K, Chandrasekhar K B. J Fluorine Chem, 2012, 135: 91
60. [60]
  [60] Donelson J L, Gibbs R A, De S K. J Mol Catal A, 2006, 256: 309
61. [61]
  [61] Heravi M M, Bakhtiari K, Javadi N M, Bamoharram F F, Saeedi M, Oskooie H A. J Mol Catal A, 2007, 264: 50
62. [62]
  [62] Tajbakhsh M, Alinezhad H, Norouzi M, Baghery S, Akbari M. J Mol Liq, 2013, 177: 44
63. [63]
  [63] Ko S, Yao C F. Tetrahedron, 2006, 62: 7293
64. [64]
  [64] Kumar A, Maurya R A. Tetrahedron Lett, 2007, 48: 3887
65. [65]
  [65] Sapkal S B, Shelke K F, Shingate B B, Shingare M S. Tetrahedron Lett, 2009, 50: 1754
66. [66]
  [66] Saha M, Pal A K. Tetrahedron Lett, 2011, 52: 4872
67. [67]
  [67] Zare A, Abi F, Moosavi-Zare A R, Beyzavi M H, Zolfigol M A. J Mol Liq, 2013, 178: 113
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