Citation: Nader Ghaffari Khaligh. Synthesis of benzo[g]indeno[2,1-b]quinoline derivatives via four-component and one-pot synthesis in presence of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate[J]. Chinese Journal of Catalysis, ;2014, 35(11): 1858-1863. doi: 10.1016/S1872-2067(14)60186-8 shu

Synthesis of benzo[g]indeno[2,1-b]quinoline derivatives via four-component and one-pot synthesis in presence of 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate

Nader Ghaffari Khaligh ^,

1.
Research House of Professor Reza, Education Guilan, Rasht, District 1, 41569-17139, Iran

Corresponding author: Nader Ghaffari Khaligh,
Received Date: 3 May 2013
Available Online: 2 June 2014
Fund Project:

A simple and facile synthesis of 12-arylbenzo[g]indeno[2,1-b]quinoline-6,11,13-trione derivatives was accomplished by the one-pot condensation of 2-hydroxynaphthalene-1,4-dione, aryl aldehydes, 2H-indene-1,3-dione, and ammonium acetate under solvent-free conditions in the presence of a Brönsted ionic liquid catalyst, namely 3-methyl-1-sulfonic acid imidazolium hydrogen sulfate.
1. [1]
  [1] Brock E D, Lewis D M, Yousaf T I, Harper H H. WO Patent 9 951 688, 1999
2. [2]
  [2] Beagley P, Blackie M A L, Chibale K, Clarkson C, Meijboom R, Moss J R, Smith P J, Su H. Dalton Trans, 2003: 3046
3. [3]
  [3] 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
4. [4]
  [4] Ma Z Z, Hano Y, Nomura T, Chen Y J. Bioorg Med Chem Lett, 2004, 14: 1193
5. [5]
  [5] Denton T T, Zhang X D, Cashman J R. J Med Chem, 2005, 48: 224
6. [6]
  [6] Sakata G, Makino K, Karasawa Y. Heterocycles, 1988, 27: 2481
7. [7]
  [7] Demeunynck M, Moucheron C, Mesmaeker A K D. Tetrahedron Lett, 2002, 43: 261
8. [8]
  [8] Lin X F, Cui S L, Wang Y G. Tetrahedron Lett, 2006, 47: 4509
9. [9]
  [9] Tsai A S, Tauchert M E, Bergman R G, Ellman J A. J Am Chem Soc, 2011, 133: 1248
10. [10]
  [10] Kakiuchi F, Kochi T, Mutsutani H, Kobayashi N, Urano S, Sato M, Nishiyama S, Tanabe T. J Am Chem Soc, 2009, 131: 11310
11. [11]
  [11] Yu W Y, Sit W N, Lai K M, Zhou Z Y, Chan A S C. J Am Chem Soc, 2008, 130: 3304
12. [12]
  [12] Aramoto H, Obora Y, Ishii Y. J Org Chem, 2009, 74: 628
13. [13]
  [13] Wang X S, Li Q, Yao C S, Tu S J. Eur J Org Chem, 2008: 3513
14. [14]
  [14] Kozlov N G, Gusak K N. Russ J Org Chem, 2008, 44: 1049
15. [15]
  [15] Hewlins M J E, Salter R. Synthesis, 2007: 2157
16. [16]
  [16] Yadav J S, Reddy B V S, Srinivas R, Madhuri Ch, Ramalingam T. Synlett, 2001: 240
17. [17]
  [17] Lu X L, Petersen J L, Wang K K. Org Lett, 2003, 5: 3277
18. [18]
  [18] Cho C S, Kim B T, Choi H J, Kim T J, Shim S C. Tetrahedron, 2003, 59: 7997
19. [19]
  [19] Sunami T, Nishio K, Kanzawa F, Fukuoka K, Kudoh S, Yoshikawa J, Saijo N. Cancer Chemother Pharmacol, 1999, 43: 394
20. [20]
  [20] Antony S, Jayaraman M, Laco G, Kohlhagen G, Kohn K W, Cushman M, Pommier Y. Cancer Res, 2003, 63: 7428
21. [21]
  [21] Mansake R H F, Kulka M. Org React, 1953, 7: 59
22. [22]
  [22] Povarov L S. Russ Chem Rev, 1967, 36: 656
23. [23]
  [23] Kouznetsov V V. Tetrahedron, 2009, 65: 2721
24. [24]
  [24] Haghighi M G, Rashidi M, Nabavizadeh S M, Jamali S, Puddephatt R J. Dalton Trans, 2010, 39: 11396
25. [25]
  [25] Baratta W, Fanfoni L, Magnolia S, Siega K, Rigo P. Eur J Inorg Chem, 2010: 1419
26. [26]
  [26] Prema D, Wiznycia A V, Scott B M T, Hilborn J, Desper J, Levy C J. Dalton Trans, 2007: 4788
27. [27]
  [27] Bierer D E, Dubenko L G, Zhang P S, Lu Q, Imbach P A, Garofalo A W, Phuan P W, Fort D M, Litvak J, Gerber R E, Sloan B, Luo J, Cooper R, Reaven G M. J Med Chem, 1998, 41: 2754
28. [28]
  [28] Venugopalan B, Bapat C P, DeSouza E P, DeSouza N J. Indian J Chem B, 1992, 31: 35
29. [29]
  [29] Deady L W, Desneves J, Kaye A J, Finlay G J, Baguley B C, Denny W A. Bioorg Med Chem, 2000, 8: 977
30. [30]
  [30] Rampa A, Bisi A, Belluti F, Gobbi S, Valenti P, Andrisano V, Cavrini V, Cavalli A, Recanatini M. Bioorg Med Chem, 2000, 8: 497
31. [31]
  [31] Lankin D C, Zimmer H. J Heterocyclic Chem, 1973, 10: 1035
32. [32]
  [32] Gorlitzer K, Weber J. Arch Pharm, 1981, 314: 76
33. [33]
  [33] Lu X L, Petersen J L, Wang K K. Org Lett, 2003, 5: 3277
34. [34]
  [34] Sawada Y, Kayakiri H, Abe Y, Imai K, Mizutani T, Inamura N, Asano M, Aramori I, Hatori C, Katayama A, Oku T, Tanaka H. J Med Chem, 2004, 47: 1617
35. [35]
  [35] Groisy-Delcey M, Groisy A, Carrez D, Huel C, Chiaroni A, Ducrot P, Bisagni E, Jin L, Leclercq G. Bioorg Med Chem, 2000, 8: 2629
36. [36]
  [36] Cheng C H, Chen R M, Huang C W, Yang C C. US Patent 0025995A1. 2005
37. [37]
  [37] Kim J I, Shin I S, Kim H, Lee J K. J Am Chem Soc, 2005, 127: 1614
38. [38]
  [38] Thompson M E, Ma B W, Djurovich P. US Patent 0164031A1. 2005
39. [39]
  [39] Parvulescu V I, Hardacre C. Chem Rev, 2007, 107: 2615
40. [40]
  [40] Rogers R D, Seddon K R. Ionic Liquids: Industrial Applications for Green Chemistry. Washington: Am Chem Soc, 2002
41. [41]
  [41] 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
42. [42]
  [42] Gu Y L, Shi F, Deng Y Q. J Mol Catal A, 2004, 212: 71
43. [43]
  [43] Niknam K, Damya M. J Chin Chem Soc, 2009, 56: 659
44. [44]
  [44] Tajik H, Niknam K, Sarrafan M. Synth Commun, 2011, 41: 2103
45. [45]
  [45] Khaligh N G, Mihankhah T. Res Chem Intermed, DOI 10.1007/ s11164-014-1552-6
46. [46]
  [46] Khaligh N G, Mihankhah T. Chin J Catal (催化学报), 2013, 34: 2167
47. [47]
  [47] Khaligh N G. Chin J Catal (催化学报), 2014, 35: 474
48. [48]
  [48] Khaligh N G. J Mol Catal A, 2011, 349: 63
49. [49]
  [49] Greenberg A E, Trussell R R, Clesceri L S, Franson M A H. Standard Methods for the Examination of Water and Wastewater. 16th Ed. Washington: American Public Health Association, 1985. 532
50. [50]
  [50] To Q H, Lee Y R, Kim S H. Bull Korean Chem Soc, 2012, 33: 1170
51. [51]
  [51] Wang X S, Zhang M M, Jiang H, Yao C S, Tu S J. Tetrahedron, 2007, 63: 4439
52. [52]
  [52] Sarkar A, Roy S R, Chakraborti A K. Chem Commun, 2011, 47: 4538
53. [53]
  [53] OECD Chemical Group. Ready Biodegradability: Modified OECD Screening Test. Method 301 E. OECD Revised Guidelines for Tests for Ready Biodegradability. Paris, France, 1993
54. [54]
  [54] Garcia M T, Gathergood N, Scammells P J. Green Chem, 2005, 7: 9
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