CdO nanoparticles as an efficient, mild and recyclable catalyst for the synthesis of 2-aryl benzoxazole derivatives by grinding method
محورهای موضوعی : Iranian Journal of CatalysisAshok Borhade 1 , Bhagwat Uphade 2
1 - Department of Chemistry, Research Center, HPT Arts and RYK Science College, Nasik, 422005, India.
2 - bDepartment of Chemistry, Research Center, Padmashri Vikhe Patil College, Pravaranagar, 413713, India.
کلید واژه: Solvent free, Nano-catalyst, Benzoxazole derivatives, CdO nanoparticles, Grinding method,
چکیده مقاله :
CdO nanoparticles efficiently catalyzes the condensation of aromatic aldehydes with 2-aminophenol at room temperature to afford 2-aryl benzoxazole derivatives by grinding method. The reactions proceed under heterogeneous and mild conditions to provide 2-aryl benzoxazoles in excellent yields (87-97 %) with high purity under solvent free condition. The reaction requires short time (5-23 minutes) under moderate conditions. The purification of products by non-chromatographic methods is additional feature of this method. A series of 2-aryl bezoxazole have been successfully synthesized by this method. Ease of recycled catalyst, cleaner process, solvent free and lower catalytic loading are the most advantages of the proposed method.
[1] A. Burger, C. Hansch, P.G. Sammes, J.B. Taylor, Comprehensive Medicinal Chemistry. Pergamon Press Oxford, 1990.
[2] T. Ozlem, O. Likay, S. Esin, Y. Ismail, U. Nejat, Farmaco 53 (1998) 337-341.
[3] A. Zafer, Kaplancikli, T.Z. Gulhan, R. Gilbert, G. Kiymet, Arch. Pharma. Res. 27 (2004) 1081-1085.
[4] T. Yi- Ping, L. Yan-Wen, Inorg. Chim. Acta 362 (2009) 2033-2038.
[5] P. Kohli, S.D. Srivastava, S.K. Srivastava, J. Chin. Chem. Soc. 54 (2007) 1003-1010.
[6] J. Nishiu, M. Ito, Y. Ishida, M. Kakutani, T. Shibata, M. Matsushita, M. Shindo, Diabetes Obes. Metab. 8 (2006) 508-518.
[7] J.A. Grobler, G. Dornadula, M.R. Rice, A.L. Simcoe, D.J. Hazuda, M.D. Miller, J. Biol. Chem. 282 (2007) 8005-8010.
[8] K. Rasmussen, M.A. Hsu, Y. Yang, Neuropsycho-pharmacology 32 (2007) 786-792.
[9] I.H. Leaver, B. Milligan, Dyes Pigm. 5 (1984) 109-144.
[10] M. Terashima, M. Ishii, Y. Kanaoka, Synthesis 6 (1982) 484-485.
[11] K. Bougrin, A. Loupy, M. Soufiaoui, Tetrahedron 54 (1998) 8055-8064.
[12] J. Chang, K. Zhao, S. Pan. Tetrahedron Lett. 43 (2002) 951-954.
[13] C. Praveen, K.H. Kumar, D. Muralidharan, P.T. Perumal, Tetrahedron 64 (2008) 2369-2374.
[14] R.S. Varma, D. Kumar, J. Heterocycl. Chem. 35 (1998) 1539-1540.
[15] R.S. Varma, R.K. Saini, O. Prakash, Tetrahedron Lett. 38 (1997) 2621-2622.
[16] R.G. Srivastava, P.S. Venkataramani, Synth. Commun. 18 (1988) 1537-1544.
[17] K. Nakagawa, H. Onoue, J. Sugita, Chem. Pharm. Bull. 12 (1964) 1135-1138.
[18] S. Maddila, S.B. Jonnalagadda, J. Chil. Chem. Soc. 57 (2012) 1099-1100.
[19] Y. Liu, D. Mao, S. Lou, J. Qian, Z. Xu, J. Zhejiang Univ. Sci. B 10 (2009) 472-478.
[20] M.M. Heravi, S. Sadjadi, H.A. Oskooie, R.K. Shoar, F.F. Bamoharram, J. Chin. Chem. Soc. 55 (2008) 890-895.
[21] S. Ramineni, R.K. Kannasani, V.V.S. Peruri, Green Chem. Lett. Rev. 7 (2014) 85-89.
[22] M.D. Khunt, V.C. Kotadiya, D.J. Viradiya, B.H. Baria, U.C. Bhoya, Int. Lett. Chem. Phys. Astron. 6 (2014) 61-68.
[23] G.M. Ziarani, A. Badiei, M.S. Nahad, M. Hassanzadeh, Eur. J. Chem. 3 (2012) 433-436.
[24] H. Reyes, H.I. Beltran, E. Rivera-Becerril, Tetrahedron Lett. 52 (2011) 308-310.
[25] I.M. Baltork, A.R. Khosropour, S.F. Hojati, Catal. Commun. 8 (2007) 1865-1870.
[26] R.N. Nadaf, S.A. Siddiqui, T. Daniel, R.J. Lahoti, K.V. Srinivasan, J. Mol. Catal. A: Chem. 214 (2004) 155-160.
[27] I.M. Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, M.A. Zolfigol, S.F. Hojati, J. Iran. Chem. Soc. 5 (2008) S65-S70.
[28] M.M. Guru, M.A. Ali, T. Punniyamurthy, Org. Lett. 13 (2011) 1194-1197.
[29] B. Wang, Y. Zhang, P. Li, L. Wang, Chin. J. Chem. 28 (2010) 1697-1703.
[30] P. Saha, T. Ramana, N. Purkait, M.A. Ali, R. Paul, T. Punniyamurthy, J. Org. Chem. 74 (2009) 8719-8725.
[31] S.M. Vahdat, S.G. Raz, S. Baghery, J. Chem. Sci. 126 (2014) 579-585.
[32] F.F. Stephens, J.D. Bower, J. Chem. Soc. (1949) 2971-2972.
[33] R. Shelkar, S. Sarode, J. Nagarkar, Tetrahedron Lett. 54 (2013) 6986-6990.
[34] M.B. Madhusudana Reddy, A. Nizam, M.A. Pasha, Synth. Commun. 41 (2011) 1838-1842.
[35] W.J. Zhou, X.Zh. Zhang, X.B. Sun, B. Wang, J.X. Wang, L. Bai, Russ. Chem. Bull. Int. Ed. 62 (2013) 1244-1247.
[36] H. Sharma, N. Singh, D.O. Jang, Green Chem. 16 (2014) 4922-4930.
[37] A.V. Borhade, B.K. Uphade, D.R. Tope, J. Chem. Sci. 125 (2013) 583-589.
[38] A.V. Borhade, B.K. Uphade, D.R. Tope, Res. Chem. Intermed. 40 (2014) 211-223.
[39] A.V. Borhade, B.K. Uphade, A.G. Gadhave, Res. Chem. Intermed. 41 (2015) 1447-1458.
[40] A.V. Borhade, B.K. Uphade, J. Iran. Chem. Soc. 12 (2015) 1107-1113.
