Nano-CrY zeolite as a new and reusable catalyst for synthesis 2-aryl-1H-benzothiazoles
محورهای موضوعی : Iranian Journal of CatalysisMojgan Zendehdel 1 , Kaveh Khosravi 2 , Maryam Javadizadeh 3
1 - Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran.
2 - Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran.
3 - Department of Chemistry, Faculty of Science, Arak University, Arak 38156-8-8349, Iran.
کلید واژه: 2-Aryl-1H-benzothiazoles, Nano-CrY zeolite, nanocatalyst, 2-Aminothiophenol, Cyclocondensation,
چکیده مقاله :
The Nano-CrY zeolite synthesized and characterized by Fourier transfer infrared (FT-IR), X-ray diffraction (XRD),and Scanning electron microscopy (SEM).The result show that nano catalyst prepared with mainly particles size about 30-80 nm .The XRD show the structure of the zeolite does not collapse. This Nano-CrY zeolite has been used as new, and nontoxic catalyst for catalyzes of synthesis of 2-aryl-1H-benzothiazoles at mild condition . This procedure is simple, effective, inexpensive and green. The products were obtained in high yields and the catalyst is reusable. Since products were obtained by aqua work-up in good purity and complex purification methods are not necessary.
[1] H. Ulrich, Sci. Synth. 11 (2002) 835-912.
[2] (a) C.G. Mortimer, G. Wells, J.P. Crochard, E.L. Stone, T.D. Bradshaw, M.F. Stevens, A.D. Westwell, J. Med. Chem. 49 (2006) 179-85. (b) I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, M.F.G. Stevens, J. Med. Chem. 44 (2001) 1446-1455. (c) T.D. Bradshaw, A. D. Westwell, Curr. Med. Chem. 11 (2004) 1009-1021.
[3] M.K. Singh, R. Tilak, G. Nath, S.K. Awasthi, A. Agarwal, J. Med. Chem. 63 (2013) 635-644.
[4] (a) A. Benazzouz, T. Boraud, P. Dubedat, A. Boireau, J. M. Stutzmann, C. Gross, Eur. J. Pharmacol. 284 (1995) 299-307. (b) P. Jimonet, F. Audaiau, M. Barreau, J.C. Blanchard, A. Boireau, Y. Bour, M.H. Coleno, A. Doble, G. Doerflinger, C.D. Huu, M.H. Donat, J.M. Duchesne, P. Ganil, C. Guérémy, E. Honoré, B. Just, R. Kerphirique, S. Gontier, P. Hubert, P.M. Laduron, J.L. Blevec, M. Meunier, J.M. Miquet, C. Nemecek, M. Pasquet, O. Piot, J. Pratt, J. Rataud, M. Reibaud, J.M. Stutzmann, S. Mignani, J. Med. Chem. 42 (1999) 2828-2843.
[5] B. Lara, L. Gandia, A. Tores, R. Martinez,-Sierra, A.G. Garcia, M.G. Lopez, Eur. J. Pharmacol. 325 (1997) 109-119.
[6] (a) N. Ashizawa, T. Aotsuka, Drugs Fut. 23 (1998) 521-529. (b) T. Kotani, Y. Nagaki, A. Ishii, Y. Konishi, H. Yago, S. Suehiro, N. Okukado, K. Okamoto, J. Med. Chem. 40 (1997) 684-694.
[7] (a) G. Sato, T. Chimoto, T. Aoki, S. Hosokawa, S. Sumigama, K. Tsukidate, F. Sagami, J. Toxicol. Sci. 24 (1999) 165-17. (b) T. Naitoh, S. Kawaguchi, M. Kakiki, H. Ohe, A. Kajiwara, T. Horie, Xenobiotica 28 (1998) 269-280. (c) T. Kagaya, A. Kajiwara, S. Nagato, K. Akasaka, A. Kubota, J. Pharmacol. Exp. Ther. 278 (1996) 243-251.
[8] (a) D. J. Hadjipavlou-Litina, A.A. Geronikaki, Drug Des. Discovery 15 (1997) 199-206. (b) K. Oketani, T. Inoue, M. Murakami, Eur. J. Pharmacol. 427 (2001) 159-166.
[9] R. Paramashivappa, P. Phani Kumar, P.V. Subba Rao, A. Srinivasa Rao, Bioorg. Med. Chem. Lett. 13 (2003) 657-660.
[10] A.A. Nagel, D.R. Liston, S. Jung, M. Mahar, L.A. Vincent, D. Chapin, Y.L. Chen, S. Hubbard, J.L. Ives, S. B. Jones, J. Med. Chem. 38 (1995) 1084-1089.
[11] J.H. Matthews, R. Krishnan, M.J. Costanzo, B.E. Maryanoff, Biophys. J. 70 (1996) 2830-2837.
[12] T.H. Jonckers, M.C. Rouan, G. Haché, W. Schepens, S. Hallenberger, J. Baumeister, J.C. Sasaki, Bioorg. Med. Chem. 22 (2012) 4998-5002.
[13] S.K. Sohn, M.S. Chang, W.S. Choi, K.B. Kim, T.W. Woo, S.B. Lee, Y.K. Chung, Can. J. Physiol. Pharmacol. 77 (1999) 330-338.
[14] C.H. Chiang, C.H. Hsieh, D.W. Lu, K.D. Kao, J. Pharm. Sci. 81 (1992) 299-302.
[15] C.W. Phoon, P.Y. Ng, A.E. Ting, S.L. Yeo, M.M. Sim, Bioorg. Med. Chem. Lett. 11 (2001) 1647-1650.
[16] D. Loos, E. Sidoova, V. Sutoris, Molecules 4 (1999) 81-93.
[17] (a) A. Ben-Alloum, S. Bakkas, M. Soufiaoui, Tetrahedron. Lett. 38 (1997) 6395-6396. (b) K. Bougrin, A. Loupy, M. Soufiaoui, Tetrahedron 54 (1998) 8055-8064. (c) C. Benedi, F. Bravo, P. Uriz, E. Fernandez, C. Claver, S. Castillon, Tetrahedron. Lett. 44 (2003) 6073-6077. (d) S.–J. Choi, H.J. Park, S.K. Lee, S.W. Kim, G. Han, H.Y.P. Choo, Biorg. Med. Chem. 14 (2006) 1229-1235.
[18] (a) L.L. Joyce, G. Evindar, R.A. Batey, Chem. Commun. (2004) 446-467. (b) X.J. Mu, J.P. Zou, R.S. Zeng, J.C. Wu, Tetrahedron. Lett. 46 (2005) 4345-4347. (c) F.M. Moghaddam, H.Z. Boeini, Synlett (2005) 1612-1614. (d) D.S. Bose, M. Idrees, J. Org. Chem. 71 (2006) 8261-8263.
[19] (a) R.M. Batista, S.P.G. Costa, M.M.M. Raposo, Tetrahedron. Lett. 45 (2004) 2825-2828. (b) B.C. Ranu, R. Jana, S. Dey, Chem. Lett. 33 (2004) 274-275. (c) T. Itoh, K. Nagata, H. Ishikawa, A. Ohsawa, Heterocycles 62 (2004) 197-201. (d) K. Bougrin, A. Loupy, M. Soufiaoui, Tetrahedron 54 (1998) 8055-8064. (e) M. Hayashi, Y. Kawashita, Lett. Org. Chem. 3 (2006) 571-578. (f) R. Gupta, M. Gupta, A. Paul, Synth. Commun. 32 (2002) 3541-3547. (g) S. Rostamizadeh, S.A.G. Housaini, Phosphorus, Sulfur, Silicon Relat. Elem. 180 (2005) 1321-1326. (h) M. Okimoto, T. Yoshida, M. Hoshi, K. Hottori, M. Komata, K. Tomozawa, T. Chiba, Heterocycles 75 (2008) 35-42. (i) A.K. Chakraborti, S. Rundrawar, K.B. Jadhav, G. Kuar, S.V. Chankeshwara, Green Chem. 9 (2007) 1335-1340.
[20] (a) S. Mourtas, D. Gatos, K. Barlos, Tetrahedron. Lett. 42 (2001) 2201-2204. (b) Y. Njoya, A. Gellis, M. Crozet, P. Vanelle, Sulfur Lett. 26 (2003) 67-75. (c) A.K. Chakraborti, C. Selvam, G. Kaur, S. Bhagat, Synlett (2004) 851-854. (d) I. Yildiz-Oren, I. Yalcin, E. Aki-Sener, N. Ucarturk, Eur. J. Med. Chem. 39 (2004) 291-298. (e) C. Chen, Y.J. Chen, Tetrahedron. Lett. 45 (2004) 113-115.
[21] R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Mol. Catal. A: Chem. 214 (2004) 155-160.
[22] H. Matsushita, S.H. Lee, M. Joung, B. Clapham, K.D. Janda, Tetrahedron. Lett. 45 (2004) 313-316.
[23] S. Paul, M. Gupta, R. Gupta, Synth. Commun. 32 (2002) 3541-3547.
[24] V.J. Majo, J. Prabhakaram, J.J. Mann, S.D. Kumar, Tetrahedron. Lett. 44 (2003) 8535-8537.
[25] D. Alagille, R. M. Baldwin, G.D. Tamagnan, Tetrahedron. Lett. 46 (2005) 1349-1351.
[26] R.H. Tale, Org. Lett. 4 (2002) 1641-1642.
[27] D. Azarifar, B. Maleki, M. Setayeshnazar,
Phosphorus, Sulfur, Silicon Relat. Elem.184 (2009) 2097-2102.
[28] M. Kalhor, N. Khodaparast, M. Zendehdel, Lett. Org. Chem. 10 (2013) 573-577.
[29] M. Zendehdel, M. Kooti, M.M. Amini, J. Porous Mater. 12 (2005) 143-149.
[30] M. Kooti, M. Zendehdel, M.A. Mohammadpour, J. Inclusion Phenom. Macrocyclic Chem. 42 (2002) 265-268.
[31] M. Zendehdel, G. Cruciani, M. Dondi, J. Porous Mater. 19 (2012) 361-368.
[32] J. Liu, D. Yin, D. Yin, Z. Fu, Q. Li, G. Lu, J. Mol. Catal. A: Chem. 209 (2004) 171-177.
[33] D.W. Breck, N.Y. Tonawanda, Crystalline zeolite Y. US Patent: 3130007, 1964.
[34] M. Zendehdel, A. Mobinikhaledi, J.F. Hasanvand, J. Inclusion Phenom. Macrocyclic Chem. 9 (2007) 41-44.