A novel nano perfluoro ionic liquid as an efficient catalyst in the synthesis of chromenes under mild and solvent-free conditions

محورهای موضوعی : Iranian Journal of Catalysis

Javad Afsar ¹ (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.)
Ardeshir Khazaei ² (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.)
Mohammad Ali Zolfigol ³ (Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.)

تاریخ دریافت : 1396/10/07 تاریخ پذیرش : 1397/01/24 تاریخ انتشار : 1397/12/10

کلید واژه: Solvent-free conditions, Chromenes, Nano perfluoro ionic liquid, [mim]C6F5O, 1-Methyl-1H-imidazol-3-ium-2, 3, 4, 5, 6-pentafluorophenolate,

چکیده مقاله :

1-Methyl-1H-imidazol-3-ium 2,3,4,5,6-pentafluorophenolate [mim]C6F5O as a novel nano ionic liquid was designed, synthesized and characterized by using various techniques such as Fourier transform spectroscopy infrared (FT-IR), nuclear magnetic resonance (NMR), x-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive x-ray spectroscopy (EDX), thermal gravimetric analysis (TGA), derivative thermal gravimetric (DTG) and elemental analysis (CHN). The described nano perfluoro ionic liquid was used as an efficient catalyst in the synthesis of 2-amino-4,5-dihydropyrano[3,2-c]chromene, 3-amino-1H-benzo[f]chromene and 2-amino-4H-chromene derivatives under mild and solvent-free conditions. Short reaction times, good yields of products, easy work-up are the major advantages of this work.

منابع و مأخذ:

[1] a) E. G. Hope, A. M. Stuart, J. Fluorine Chem. 100 (1999) 75-83; b) J. A. Gladysz, D. P. Curran, Tetrahedron 58 (2002) 3823-3825; c) C. B. Murray, G. Sandford, S. R. Korn, J. Fluorine Chem. 123 (2003) 81-84; d) M. Wende, F. Seidel, J. Gladysz, J. Fluorine Chem. 124 (2003) 45-54.
[2] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 94 (1999) 183-193.
[3] a) A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000), 3168-3210; b) A. Dömling, D. Kan Wang, W. Wang, Chem. Rev. 112 (2012), 3083-3135; c) A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, J. Afsar, A. Zare, V. Khakyzadeh, M. H. Beyzavi, Chin. J. Catal. 34 (2013) 1936-1944; d) A. R. Moosavi-Zare, M. A. Zolfigol, M. Zarei, A. Zare, J. Afsar, Appl. Catal., A 505 (2015) 224-234.
[4] M. A. Zolfigol, T. Azadbakht, V. Khakyzadeh, R. Nejatyami, D. M. Perrin, RSC Adv. 4 (2014) 40036-40042.
[5] S. B. Sapkal, K. F. Shelke, B. B. Shingate, M. S. Shingare, Tetrahedron Lett. 50 (2009) 1754-1756.
[6] M. A. Zolfigol, V. Khakyzadeh, A. R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, M. H. Beyzavi, R. Luque, Green Chem. 15 (2013) 2132-2140.
[7] a) K. R. Seddon, A. Stark, M. J. Torres, Pure Appl. Chem. 72 (2000) 2275-2287; b) M. A. Zolfigol, S. Baghery, A. R. Moosavi-Zare, S. M. Vahdat, H. Alinezhad, M. Norouzi, RSC Adv. 5 (2015) 45027-45037.
[8] a) A. R. Moosavi-Zare, M. A. Zolfigol, O. Khaledian, V. Khakyzadeh, M. D. Farahani, H. G. Kruger, New J. Chem. 38 (2014) 2342-2347; b) A. Ouadi, O. Klimchuk, C. Gaillard, I. Billard, Green Chem. 9 ( 2007) 1160-1162.
[9] A. R. Moosavi-Zare, M. A. Zolfigol, V. Khakyzadeh, C. Böttcher, M. H. Beyzavi, A. Zare, A. Hasaninejad, R. Luque, J. Mater. Chem. 2 (2014) 770-777.
[10] M. A. Zolfigol, S. Baghery, A. R. Moosavi-Zare, S. M.Vahdat, RSC Adv. 5 (2015) 32933-32940.
[11] M. M. Kandeel, A. M. Kamal, E. K. Abdelall, H. A. Elshemy, Eur. J. Med. Chem. 59 (2013)183-193.
[12] T. Raj, R. K. Bhatia, M. Sharma, A. Saxena, M. Ishar, Eur. J. Med. Chem. 45 (2010) 790-794.
[13] T. Raj, R. K. Bhatia, R. K. Sharma, V. Gupta, D. Sharma, M. P. S. Ishar, Eur. J. Med. Chem. 44 (2009) 3209-3216.
[14] M. Azizmohammadi, M. Khoobi, A. Ramazani, S. Emami, A. Zarrin, O. Firuzi, R. Miri, A. Shafiee, Eur. J. Med. Chem. 59 (2013) 15-22.
[15] F. M. Abdelrazek, P. Metz, E. K. Farrag, Arch. Pharm. 337 (2004) 482-485.
[16] A. Kumar, R.A. Maurya, S. Sharma, P. Ahmad, A. Singh, G. Bhatia, A. K. Srivastava, Bioorg. Med. Chem. Lett. 19 (2009) 6447-6451.
[17] T. Symeonidis, K. C. Fylaktakidou, D. J. Hadjipavlou-Litina, K. E. Litinas, Eur. J. Med. Chem. 44 (2009) 5012-5017.
[18] M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 14 (2008) 6329-6332.
[19] a) M. A. Zolfigol, D. Habibi, B. F. Mirjalili, A. Bamoniri, Tetrahedron Lett. 44 (2003) 3345-3349; b) M. A. Zolfigol, I. Mohammadpoor-Baltork, D. Habibi, B. F. Mirjalili, A. Bamoniri, Tetrahedron Lett. 44 (2003) 8165-8167; c) M. A. Zolfigol, I. Mohammadpoor-Baltork, D. Habibi, B. F. Mirjalili, A. Bamoniri, Phosphorus, Sulfur, Silicon Relat. Elem. 179 (2004) 2189-2193.
[20] N. Karak, Fundamentals of polymers: Raw matertials to finish products, PHI learning private Ltd, New Delhi, 2009.
[21] N. Hazeri, M. T. Maghsoodlou, F. Mir, M. Kangani, H. Saravani, E. Molashahi, Chin. J. Catal. 35 (2014) 391-395.
[22] S. Khodabakhshi, B. Karami, K. Eskandari, S. J. Hoseini, C. R. Chim. 17 (2014) 35-40.
[23] K. Niknam, A. Jamali, Chin. J. Catal. 33 (2012) 1840-1849.
[24] M. A. Zolfigol, N. Bahrami-Nejad, F. Afsharnadery, S. Baghery, J. Mol. Liq. 221 (2016) 851-859.
[25] Z. Vafajoo, H. Veisi, M. T. Maghsoodlou, H. Ahmadian, C. R. Chim. 17 (2014) 301-304.
[26] M. Safaiee, M. A. Zolfigol, F. Afsharnadery, S. Baghery, RSC Adv. 5 (2015) 102340-102349.
[27] M. Kidwai, S. Saxena, M. K. R. Khan, S. S. Thukral, Bioorg. Med. Chem. Lett. 15 (2005) 4295-4298.
[28] M. M. Heravi, K. Bakhtiari, V. Zadsirjan, F. F. Bamoharram, O. M. Heravi, Bioorg. Med. Chem. Lett. 17 (2007) 4262-4265.
[29] S. Abdolmohammadi, M. Afsharpour, S. S. Keshavarz-Fatideh, Afr. J. Chem. 67 (2014) 203-210.
[30] K. Azizi, M. Karimi, H. R. Shaterian, A. Heydari, RSC Adv.4 (2014) 42220-42225.
[31] S. Javanshir, M. Safari, M. Dekamin, Sci. Iran. Trans. C 21 (2014) 742-747.
[32] S. R. Kale, S. S. Kahandal, A. S. Burange, M. B. Gawande, R. V. Jayaram, Catal. Sci. Tech. 3 (2013) 2050-2056.
[33] J. M. Khurana, B. Nand, P. Saluja, Tetrahedron 66 (2010) 5637-5641.
[34] J. M. Khurana, S. Kumar, Tetrahedron Lett. 50 (2009) 4125-4127.
[35] S. Paul, P. Bhattacharyya, A. R. Das, Tetrahedron Lett. 52 (2011) 4636-4641.
[36] M. Khoobi, L. Ma’mani, F. Rezazadeh, Z. Zareie, A. Foroumadi, A. Ramazani, A. Shafiee, J. Mol. Catal. A: Chem. 359 (2012) 74-80.
[37] Y. Wang, H. Ye, G. Zuo, J. Luo, J. Mol. Liq. 212 (2015) 418-422.
[38] M. Sedaghat, M. R. Booshehri, M. Nazarifar, F. Farhadi, Appl. Clay. Sci. 95 (2014) 55-59.
[39] M. M. Heravi, B. A. Jani, F. Derikvand, F. F. Bamoharram, H. A. Oskooie, Catal. Commun. 10 (2008) 272-275.