Application of a mesoporous nanomaterial based on basic ionic liquid anchored to silica as a highly effective catalyst for the production of 2-amino-4H-chromenes
محورهای موضوعی : Iranian Journal of Catalysis
Zahra Abshirini
1
(Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran.)
Alireza Kohzadian
2
(Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran.)
Zahra Paryav
3
(Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran.)
Abdolkarim Zare
4
(Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran.)
کلید واژه: Solvent-free conditions, Multi-component reaction, Nanocatalyst, 2-Amino-4H-chromene, Basic ionic liquid anchored to silica, Nano-2-(dimethylamino)-N-(silica-n-propyl)-N, N-dimethylethanaminium chloride {nano-[DMSPDE][Cl]},
چکیده مقاله :
This research describes application of a mesoporous nanostructured material based on basic ionic liquid anchored to silica, i.e. nano-2-(dimethylamino)-N-(silica-n-propyl)-N,N-dimethylethanaminium chloride {nano-[DMSPDE][Cl]}, as a highly effective and heterogeneous nanocatalyst for the production of 2-amino-4H-chromenes. The one-pot multi-component reaction of aromatic aldehydes with malononitrile and 1-naphthol in the presence of nano-[DMSPDE][Cl] under solvent-free conditions affords the title compounds with high yields in short times.
[1] B. Rai, R.D. Shukla, A. Kumar, Green Chem. 20 (2018) 822-826.
[2] H. Ghafuri, B. Ghorbani, A. Rashidizadeh, M. Talebi, M. Roshani, Appl. Organomet. Chem. 32 (2018) e4147.
[3] A. Maleki, Ultrason. Sonochem. 40 (2018) 460-464.
[4] F. Manouchehri, B. Sadeghi, F. Najafi, M.H. Mosslemin, J. Iran. Chem. Soc. 15 (2018) 1673-1683
[5] S. Sajjadifar, Z. Gheisarzadeh, Appl. Organomet. Chem. 33 (2019) e4602.
[6] M. Akrami Abarghooei, R. Mohebat, Z. Karimi-Jaberi, M. H. Mosslemin, Catal. Commun. 105 (2018) 59-64.
[7] G. Mohammadi Ziarani, P. Gholamzadeh, A. Badiei, V. Fathi Vavsari, Res. Chem. Intermed. 44 (2018) 277-288.
[8] A. Zare, A. Kohzadian, Z. Abshirini, S. S. Sajadikhah, J. Phipps, M. Benamara, M.H. Beyzavi, New J. Chem. 43 (2019) 2247-2257.
[9] A. Zare, M. Merajoddin, A.R. Moosavi-Zare, M. Zarei, M.H. Beyzavi, M.A. Zolfigol, Res. Chem. Intermed. 42 (2016) 2365-2378.
[10] R. Mohammadi, S. Esmati, M. Gholamhosseini-Nazari, R. Teimuri-Mofrad, J. Mol. Liq. 275 (2019) 523-534.
[11] M. Mamaghani, M. Sheykhan, M. Sadeghpour, F. Tavakoli, Monatsh. Chem. 149 (2018) 1437-1446.
[12] A. Zare, E. Sharif, A. Arghoon, M. Ghasemi, B. Dehghani, S. Ahmad-Zadeh, F. Zarei, Iran. J. Catal. 7 (2017) 233-241.
[13] F. Tamaddon, D. Azadi, J. Mol. Liq. 255 (2018) 406-412.
[14] N. Irannejad-Gheshlaghchaei, A. Zare, S.S. Sajadikhah, A. Banaei, Res. Chem. Intermed. 44 (2018) 6253-6266.
[15] A.S. Díaz-Marta, C.R. Tubío, C. Carbajales, C. Fernández, L. Escalante, E. Sotelo, F. Guitián, V.L. Barrio, A. Gil, A. Coelho, ACS Catal. 8 (2018) 392-404.
[16] T. Salehi-Hamzehkhani, M. Hatami, A. Zare, A.R. Moosavi-Zare, A. Parhami, Z. Khedri, H. Kabgani, M. Beikagha, R. Salamipoor, Iran. J. Catal. 4 (2014) 295-303.
[17] H.H. Mardhiah, H.C. Ong, H.H. Masjuki, S. Lim, H.V. Lee, Renewable Sustainable Energy Rev. 67 (2017) 1225-1236.
[18] R.V.A. Orru, E. Ruijter, Topics in Heterocyclic Chemistry, Vol. 23, Springer-Verlag, Berlin/Heidelberg, 2010.
[19] M. Karami, A. Zare, Org. Chem. Res. 4 (2018) 174-181.
[20] M. Bakherad, A. Keivanloo, A.H. Amin, P. Ghamari Kargar, Iran. J. Catal. 8 (2018) 179-187.
[21] M. Beyrati, A. Hasaninejad, Tetrahedron Lett. 58 (2017) 1947-1951.
[22] A. Zare, Z. Nasouri, J. Mol. Liq. 216 (2016) 364-369.
[23] G. Harichandran, P. Parameswari, P. Shanmugam, Dyes Pigm. 139 (2017) 541-548.
[24] M.M. Khafagy, A.H.F.A. El-Wahas, F.A. Eid, A.M. El-Agrody, Il Farmaco 57 (2002) 715-722.
[25] A. Martínez-Grau, J. Marco, Bioorg. Med. Chem. Lett. 7 (1997) 3165-3170.
[26] S.J. Mohr, M.A. Chirigos, F.S. Fuhrman, J.W. Pryor, Cancer Res. 35 (1975) 3750-3754.
[27] K. Hiramoto, A. Nasuhara, K. Michiloshi, T. Kato, K. Kikugawa, Mutat. Res. Genet. Toxicol. Environ. Mutagen. 395 (1997) 47-56.
[28] G. Bianchi, A. Tava, Agric. Biol. Chem. 51 (1987) 2001-2002.
[29] C.P. Dell, C.W. Smith, Eur. Pat. Appl. EP 537949 (1993); Chem. Abstr. 119 (1993) 139102d.
[30] K. Gorlitzer, A. Dehre, E. Engler, Arch. Pharm. Weinheim Ger. 316 (1983) 264-270.
[31] E.R. Bissell, A.R. Mitchell, R.E. Smith, J. Org. Chem. 45 (1980) 2283-2287.
[32] G.A. Reynolds, K.H. Drexhage, Opt. Commun. 13 (1975) 222-225.
[33] H. Zollinger, Color Chemistry, 3rd ed., Wiley-VCH, Weinheim, 2003.
[34] A. Mobinikhaledi, H. Moghanian, M. Ghanbari, Appl. Organomet. Chem. 32 (2018) e4108.
[35] S.M. Baghbanian, N. Rezaei, H. Tashakkorian, Green Chem. 15 (2013) 3446-3458.
[36] M.A. Zolfigol, M. Yarie, S. Baghery, Synlett 27 (2016) 1418-1422.
[37] T.-S. Jin, J.-C. Xiao, S.-J. Wang, T.-S. Li, Ultrason. Sonochem. 11 (2004) 393-397.
[38] M. Mirza-Aghayan, S. Nazmdeh, R. Boukherroub, M. Rahimifard, A.A. Tarlani, M. Abolghasemi-Malakshah, Synth. Commun. 43 (2013) 1499-1507.
[39] S. Taghavi Fardood, A. Ramazani, P. Azimzadeh Asiabi, Y. Bigdeli Fard, B. Ebadzadeh, Asian J. Green. Chem. 1 (2017) 34-40.
[40] S. Sadjadi, M.M. Heravi, V. Zadsirjan, M. Ebrahimizadeh, Res. Chem. Intermed. 43 (2017) 5467-5483.
[41] A. Mohammadinezhad, B. Akhlaghinia, Aust. J. Chem. 71 (2018) 32-46.
[42] K. Kantharaju, S.Y. Khatavi, ChemistrySelect 3 (2018) 5016-5024.
[43] M.S. Rao, B.S. Chhikara, R. Tiwari, A. Nasrolahi Shirazi, K. Parang, A. Kumar, Chem. Biol. Interface 2 (2012) 362-372.
