Nano-BF3/cellulose as a biodegradable novel catalyst for synthesis of highly functionalized tetrahydropyridines

Iranian Journal of Catalysis

مقاله 5، دوره 9، شماره 4، اسفند 2019، صفحه 321-328   

نوع مقاله: Articles

نویسندگان

Seyede Azita Fazeli-Attar؛ Bi Bi Fatemeh Mirjalili^*

Department of Chemistry, College of Science, Yazd University, Yazd, P.O. Box. 89195-741, I. R. Iran.

چکیده

Nano-cellulose with high amount of free OH groups could be used as supporting agents for boron trifluoride (BF₃). Nano-BF₃/cellulose is a solid acid and a biodegradable catalyst which was prepared via reaction of nano-cellulose and BF₃. The structure of this catalyst was studied by FT-IR, FESEM, TEM, XRD, EDS, TGA, XRF and BET. In this research, the synthesis of highly functionalized tetrahydropyridines has been developed via a five-component reaction of aldehyde, amine and ethyl acetoacetate using nano-BF₃/cellulose under solvent-free conditions. The structures of obtained products were identified by FTIR, ¹H NMR and ¹³C NMR. Some advantages of this protocol are high to good yields, environmentally benign procedure, easy work-up of reaction and moderate reusability of the catalyst.

کلیدواژه‌ها

Multicomponent reactions؛ Tetrahydropyridines؛ Nano-BF3/cellulose؛ Solid acid

مراجع

[1] L. Constantino, D. Barlocco, Curr. Med. Chem. 13 (2008) 65-85.
[2] A. Zare, E. Sharif, A. Arghoon, M. Ghasemi, B. Dehghani, S. Ahmad-Zadeh, F. Zarei, Iran. J. Catal. 7 (2017) 233-241.
[3] R. Magar, G. Pawar, S. Gadekar, M. Lande, Iran. J. Catal. 7 (2017) 1-9.
[4] R. Singh, S. Sharma, A. Sandhar, M. Saini, S. Kumar, Iran. J. Catal. 6 (2016) 1-21.
[5] R. Singh, R. Bala, R. Duvedi, S. Kumar, Iran. J. Catal. 5 (2015) 187-206.
[6] M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17 (2009) 625-633.
[7] R. Aeluri, M. Alla, V.R. Bommena, R. Murthy, N. Jain, Asian J. Org. Chem. 1 (2012) 71-79.
[8] J. Stephen, M.D. Peroutka, H. Solomon, M.D. Snyder, Am. J. Psych. 137 (1980) 1518-1522.
[9] A.D. Korczyn, Expert Opin. Investig. Drugs 9 (2000) 2259-2267.
[10] H. Kitagawa, T. Takenouchi, R. Azuma, K.A. Wesnes, W.G. Kramer, D.E. Clody, A.L. Burnett, Neuropsychopharmacology 28 (2003) 542-551.
[11] M.D. Mashkovskii, R.G. Glushkov, Pharm. Chem. J. 35 (2001) 179-182.
[12] A.T. Khan, T. Parvin, L.H. Choudhury, J. Org. Chem. 73 (2008) 8398-8402.
[13] T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51 (2010) 4419-4424.
[14] T. Khan, M.M. Khan, K.K.R. Bannuru, Tetrahedron 66 (2010) 7762-7772.
[15] H.J. Wang, L.P. Mo, Z.H. Zhang, ACS Comb. Sci.13 (2011) 181-185.
[16] S. Mishra, R. Ghosh, Tetrahedron Lett. 52 (2011) 2857-2861.
[17] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.J. Shams-Najafi, Monatsh Chem. 143 (2012) 939-945.
[18] N. Hazeri, M.T. Maghsoodlou, S.M. Habibi‐Khorassani, J. Aboonajmi, S.S. Sajadikhah, J. Chin. Chem. Soc. 60 (2013) 355-358.
[19] J. Safaei-Ghomi, A. Ziarati, J. Iran. Chem. Soc. 10 (2013) 135-139.
[20] M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun. 43 (2013) 635-644.
[21] R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68 (2012) 363-369.
[22] G. Harichandran, S.D. Amalraj, P. Shanmugam, J. Heterocyclic Chem. 50 (2013) 539-543.
[23] H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyedi, M. Abbasi, RSC Adv. 4 (2014) 39782-39789.
[24] N.R. Agrawal, S.P. Bahekar, P.B. Sarode, S.S. Zade, H.S. Chandak, RSC Adv. 5 (2015) 47053-47059.
[25] M. Daraei, M.A. Zolfigol, F. Derakhshan-Panah, M. Shiri, H.G. Kruger, M. Mokhlesi, J. Iran. Chem. Soc. 12 (2015) 855-861.
[26] M. Kataria, S. Pramanik, M. Kumar, V. Bhalla, Chem. Commun. 51 (2015) 1483-1486.
[27] M. Abbasi, S.M. Seyedi, H. Sadeghian, M. Akhbari, M. Enayaty, A. Shiri, Heterocycl. Commun. 22 (2016) 117-121.
[28] M. Maghsoodlou, N. Hazeri, E. Fereidooni, S. Salahi, N. Mahmoudabadi, N. Khorshidi, J. Aboonajmi, M. Lashakri, Iran. J. Catal. 5 (2015) 245-252.
[29] Z. Benzekribe, H. Serrar, A. Zarguil, S. Boukhris, A. Souizi, Iran. J. Catal. 8 (2018) 1-7.
[30] S.C. Azimi, H. Kefayati, Iran. J. Catal. 3 (2013) 123-128.
[31] K.F. Shelke, S.B. Sapkal, G.K. Kakade, B.B. Shingate, M.S. Shingare, Green Chem. Lett. Rev. 3 (2010) 27-32.
[32] J. Safari, S.H. Banitaba, S.D. Khalili, J. Mol. Catal A: Chem. 335 (2011) 46-50.
[33] S. Azad, B.F. Mirjalili, RSC Adv. 6 (2016) 96928-96934.
[34] C. Mukhopadhyay, S. Rana, R.J. Butcher, A.M. Schmiedekamp, Tetrahedron Lett. 52 (2011) 5835-5840.
[35] E. Babaei, B. F. Mirjalili, Res. Chem. Intermed. 44 (2018) 3493–3505.