Ultrasonic activated efficient synthesis of chromenes using amino-silane modified Fe3O4 nanoparticles: A versatile integration of high catalytic activity and facile recovery

Journal of Molecular Structure

Volumn 1072, Issue 1, 2014, Pages 53-60

  Safari, Javad ^a   Zarnegar, Zohre ^a  

^a UNIVERSITY OF KASHAN   (Iran)

Author keywords

2 Amino 4H chromene; Heterogeneous catalyst; Malononitrile; Ultrasonic

Indexed keywords

MOLECULAR STRUCTURE; STRUCTURE (COMPOSITION); ULTRASONICS;

2-AMINO-4H-CHROMENE; CATALYTIC TRANSFORMATION; HETEROGENEOUS CATALYST; MAGNETIC NANO-PARTICLES; MALONONITRILES; MILD REACTION CONDITIONS; THREE-COMPONENT COUPLING REACTION; ULTRASOUND IRRADIATION;

NANOPARTICLES;

EID: 84903317300     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2014.04.023     Document Type: Article

References (72)

1. C. Larksarp, and H. Alper J. Org. Chem. 65 2000 2773 2777
2. V. Krchnak, and M.W. Holladay Chem. Rev. 102 2002 61 91
3. B.B. Tour, and D.G. Hall Chem. Rev. 109 2009 4439 4486
4. S.M. Roopan, F.N. Khan, and B.K. Mandal Tetrahedron Lett. 51 2010 2309 2311
5. G.R Green, J.M Evans, and A.K Vong In Comprehensive Heterocyclic Chemistry II A.R. Katritzky, C.W. Rees, E.F.V. Scriven, vol. 5 1995 Springer Berlin 469
6. B.M. Rao, G.N. Reddy, T.V. Reddy, B.L.A. Prabhavathi Devi, R.B.N. Prasad, J.S. Yadav, and B.V. Subba Reddy Tetrahedron Lett. 54 2013 2466 2471
7. G. Kolokythas, N. Pouli, P. Marakos, H. Pratsinis, and D. Kletsas Eur. J. Med. Chem. 41 2006 71 79
8. M.A. Azuine, H. Tokuda, J. Takayasu, F. Enjyo, T. Mukainaka, T. Konoshima, H. Nishino, and G. Kapadia J. Pharmacol. Res. 49 2004 161 169
9. S.K. Srivastava, R.P. Tripathi, and R. Ramachandran J. Biol. Chem. 280 2005 30273 30281
10. H. Brotz-Oesterhelt, I. Knezevic, S. Bartel, T. Lampe, U. Warnecke- Eberz, K. Ziegelbauer, D. Habich, and H. Labischinski J. Biol. Chem. 278 2003 39435 39442
11. S. Toshiro, W. Noriko, Eur. Pat. Appl. EP 647445 A1 19950412, 1995.
12. Y. Ito, H. Kato, S. Yasuda, N. Kato, N. Iwasaki, H. Nishino, M. Takeshita, Jpn. Kokai Tokkyo Koho, JP 06107664 A2 19940419, 1994.
13. K. Goto, O. Yaoka, T. Oe, PCT Int. Appl. WO 8401711 A1 19840510, 1984.
14. Y. Maruyama, K. Goto, M. Terasawa, Ger. Offen. DE 3010751 19810806, 1981.
15. K. Ukawa, T. Ishiguro, H. Kuriki, and A. Nohara Chem. Pharm. Bull. 33 1985 4432 4437
16. G.P Ellis The Chemistry of Heterocyclic Compounds A. Weissberger, E.C. Taylor, Chromenes, Chromanes, and Chromones 1977 John Wiley New York, NY 13 (Chap. 2)
17. F.M. Abdel Galil, B.Y. Riad, S.M. Sherif, and M.H. Elnagdi Chem. Lett. 1982 1123 1126
18. R.S. Varma, and R. Dahiya J. Org. Chem. 63 1998 8038 8041
19. R.W. DeSimone, K.S. Currie, S.A. Mitchell, J.W. Darrow, and D.A. Pippin Comb. Chem. High Throughput Screen 7 2004 473 494
20. A.A. Patchett, and R.P. Nargund Annu. Rep. Med. Chem. 35 2000 289 298
21. L. Bonsignore, G. Loy, D. Secci, and A. Calignano Eur. J. Med. Chem. 28 1993 517 520
22. M.S. Singh, and S. Chowdhury RSC Adv. 2 2012 4547 4592
23. G. Zhang, Y. Zhang, J. Yan, R. Chen, S. Wang, Y. Ma, and R. Wang J. Org. Chem. 77 2012 878 888
24. N.M. Sabry, H.M. Mohamed, E.S.A.E.H. Khattab, S.S. Motlaq, and A.M. El-Agrody Eur. J. Med. Chem. 46 2011 765 772
25. J.S. kommer, D. Wlodkowic, M. Matto, M. Eray, and J. Pelkonen Leukemia Res. 30 2006 322 331
26. W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, C. Crogan-Grundy, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. Gourdeau, B. Tseng, J. Drewe, and S.X. Cai Bioorg. Med. Chem. Lett. 15 2005 4745 4751
27. H. Gourdeau, L. Leblond, B. Hamelin, C. Desputeau, K. Dong, I. Kianicka, D. Custeau, C. Bourdeau, L. Geerts, S.X. Cai, J. Drewe, D. Labrecque, S. Kasibhatla, and B. Tseng Mol. Cancer Ther. 3 2004 1375 1384
28. M.G. Dekamin, M. Eslami, and A. Maleki Tetrahedron 69 2013 1074 1085
29. T.S. Jin, J.C. Xiao, S.J. Wang, and T.S. Li Ultrason. Sonochem. 11 2004 393 397
30. T.S. Jin, J.S. Zhang, L.B. Liu, A.Q. Wang, and T.S. Li Synth. Commun. 36 2006 2009 2015
31. D.Q. Shi, S.I. Zhang, Q.Y. Zhuang, and X.S. Wang Chin. J. Org. Chem. 23 2003 877 879
32. T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, and X.R. Song Synlett 2003 2001 2004
33. C. Lu, X.J. Huang, Y.Q. Li, M.Y. Zhou, and W. Zheng Monatsh. Chem. 140 2009 45 47
34. L. Chen, Y.Q. Li, X.J. Huang, and W.J. Zheng Heteroat. Chem. 20 2009 91 94
35. M.M. Heravi, K. Bakhtiari, V. Zadsirjan, and F.F. Bamoharram Bioorg. Med. Chem. Lett. 17 2007 4262 4265
36. J.F. Zhou, S.J. Tu, Y. Gao, and M. Ji Chin. J. Org. Chem. 21 2001 742 745
37. K. Rad-Moghadam, and L. Yoseftabar-Miri Tetrahedron 67 2011 5693 5699
38. M.J. Khurana, B. Nand, and P. Saluja Tetrahedron 66 2010 5637 5641
39. D.S. Raghuvanshi, and K.N. Singh Arkivoc. 10 2010 305 317
40. W. Kemnitzer, S. Kasibhatla, S. Jiang, H. Zhang, J. Zhao, S. Jia, L. Xu, C. Crogan-Grundy, R. Denis, N. Barriault, L. Vaillancourt, S. Charron, J. Dodd, G. Attardo, D. Labrecque, S. Lamothe, H. gourdeau, B. Tseng, J. Drewe, and S.X. Cai Bioorg. Med. Chem. Lett. 15 2005 4745 4751
41. B. Datta, and M.A. Pasha Ultrason. Sonochem. 19 2012 725 728
42. S. Shylesh, V. Schünemann, and W.R. Thiel Angew. Chem. Int. Ed. 49 2010 3428 3459
43. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, and J.M. Basset Chem. Rev. 111 2011 3036 3075
44. J. Safari, Z. Zarnegar, and M. Heydarian Bull. Chem. Soc. Jpn. 85 2012 1332 1338
45. E. Karaoǧlu, U. Özel, C. Caner, A. Baykal, M.M. Summaka, and H. Sözeri Mater. Res. Bull. 47 2012 4316 4321
46. A.H. Lu, E.L. Salabas, and F. Schuth Angew. Chem. Int. Ed. 46 2007 1222 1244
47. Ma. Nasr-Esfahani, S.J. Hoseini, M. Montazerozohori, R. Mehrabi, and H. Nasrabadi J. Mol. Catal. A: Chem. 382 2014 99 105
48. Y. Zhu, L.P. Stubbs, F. Ho, R. Liu, C.P. Ship, J.A. Maguire, and N.S. Hosmane Chem. Catal. Chem. 2 2010 365 374
49. F. Zamani, S.M. Hosseini, and S. Kianpour Solid State Sci. 26 2013 139 143
50. B. Hu, J. Pan, H.L. Yu, J.W. Liu, and J.H. Xu Process Biochem. 44 2009 1019 1024
51. C.S. Gill, B.A. Price, and C.W. Jones J. Catal. 251 2007 145 152
52. A. Taher, J.B. Kim, J.Y. Jung, W.S. Ahn, and M.J. Jin Synlett 2009 2477 2482
53. O.C. Dalaigh, A.S. Corr, Y. Gun'ko, and J.S. Connon Angew. Chem. Int. Ed. 46 2007 4329 4332
54. Y. Zhang, Y. Zhao, and C. Xia J. Mol. Catal. A: Chem. 306 2009 107 112
55. C.W. Lim, and I.S. Lee Nano Today 5 2010 412 434
56. M.Z. Kassaee, H. Masrouri, and F. Movahedi Appl. Catal. A: Gen. 395 2011 28 33
57. K.C. Barick, M. Aslam, P.V. Prasad, V.P. Dravid, and D. Bahadur J. Magn. Magn. Mater. 321 2009 1529 1532
58. K. Can, M. Ozmen, and M. Ersoz Colloid Surf. B 71 2009 154 159
59. H. Cao, J. He, L. Deng, and X. Gao Appl. Surf. Sci. 255 2009 7974 7980
60. J. Safari, and Z. Zarnegar Ultrason. Sonochem. 20 2013 740 746
61. M. Seenuvasan, C.G. Malar, S. Preethi, N. Balaji, J. Iyyappan, M. Anil Kumar, and K.S. Kumar Mater. Sci. Eng. C 33 2013 2273 2279
62. A. Rostami, B. Tahmasbi, H. Gholami, and H. Taymorian Chin. Chem. Lett. 24 2013 211 214
63. M. Esmaeilpour, A.R. Sardarian, and J. Javidi Appl. Catal. A: Gen. 445-446 2012 359 367
64. M. Demirelli, E. Karaoǧlu, A. Baykal, H. Sozeri, and E. Uysal J. Alloy. Compd. 582 2014 201 207
65. Y. Tan, M. Chen, and Y. Hao Chem. Eng. J. 191 2012 104 111
66. T.J. Daou, J.M. Grene'che, G. Pourroy, S. Buathong, A. Derory, C. Ulhaq Bouillet, B. Donnio, D. Guillon, and S. Begin Colin Chem. Mater. 20 2008 5869 5875
67. M.E. Fleet Acta Cryst. B 37 1981 917 920
68. S. Kanimozhi, and K. Perinbam Mater. Res. Bull. 48 2013 1830 1836
69. M. Kidwai, S. Saxena, M.K.R. Khanb, and S.S. Thukral Bioorg. Med. Chem. Lett. 15 2005 4295 4298
70. H. Eshghi, S. Damavandi, and G.H. Zohuri Synth. React. Inorg. Met. Org. Chem. 41 2011 1067 1073
71. S.K. Kundu, J. Mondal, and A. Bhaumik Dalton Trans. 42 2013 10515 10524
72. S. Khaksar, A. Rouhollahpour, and S. Mohammadzadeh Talesh J. Fluorine Chem. 141 2012 11 15