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

Iranian Journal of Catalysis

مقاله 5، دوره 9، شماره 1، خرداد 2019، صفحه 37-49   

نوع مقاله: Articles

نویسندگان

Javad Afsar؛ Ardeshir Khazaei^* ؛ Mohammad Ali Zolfigol^*

Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran.

چکیده

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.

کلیدواژه‌ها

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

سایر فایل های مرتبط با مقاله

SI.pdf

مراجع

[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.