Document Type : Original Research Article

Authors

Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran.

Abstract

This work described a simple and efficient synthesis of dialkyl 3-(alkylamino)-1-aryl-1H-pyrazole-4,5-dicarboxylates via a three component reaction between arylhydrazine, alkylisocyanid and dialkylacetylenedicarboxylates in the presence of phenylisocyanate and α-Fe2O3 nanoparticles. Eco friendly, solvent-free conditions, excellent yields, and short reaction times, inexpensive and readily available catalysts are the main advantages of this method. In this work, phenylisocyanate and α-Fe2O3 nanoparticles used as a potent mixed catalyst for promoting the reaction and taking it in a special way to obtain the titled compounds in good to excellent yields. This reaction was not carried out without any of the components of this mixed catalyst. It means that for performance this reaction both of the mixed catalyst components is required.

Graphical Abstract

One-pot three-component synthesis of dialkyl 3-(alkylamino)-1-aryl-1H-pyrazole-4,5-dicarboxylates using α-Fe2O3 nanoparticles and phenylisocyanate in solvent-free conditions

Keywords

Main Subjects

[1] A. Domling, I. Ugi, International Edition, 2000, 39, 3168-3210.
[2] R.C. Cioc, E. Ruijter, R.V. Orru, Green Chemistry, 2014, 16, 2958-2975.
[3] V. Nair, C. Rajesh, A. Vinod, S. Bindu, A. Sreekanth, J. Mathen, L. Balagopal, Accounts of chemical research, 2003, 36, 899-907.
[4] B. Mohammadi, M. Shafieey, H. Kazemi, A. Ramazani, Chinese Chemical Letters, 2013, 24, 497-499.
[5] B. Mohammadi, M. Adib, Chinese Chemical Letters, 2014, 25, 553-556.
[6] J. Taran, A. Ramazani, S. Woo Joo, K. Slepokura, T. Lis, Helvetica ChimicaActa, 2014,97, 1088-1096.
[7] A. Ramazani, M. Khoobi, A. Torkaman, F.Z. Nasrabadi, H. Forootanfar, M. Shakibaie, M. Jafari, A. Ameri, S. Emami, M.A. Faramarzi, European journal of medicinal chemistry, 2014,78, 151-156.
[8] A. Ramazani, A.T. Mahyari, M. Rouhani, A. Rezaei, Tetrahedron Letters, 2009, 50, 5625-5627.
[9] A.R. Kazemizadeh, A. Ramazani, Arkivoc, 2008, 15, 159-165.
[10] A.R. Kazemizadeh, A. Ramazani, Journal of the Brazilian Chemical Society, 2009, 20, 309-312.
[11] A. Ramazani, N. Noshiranzadeh, A. Ghamkhari, K. Ślepokura, T. Lis, Helvetica ChimicaActa, 2008,91,252-2261.
[12] A. Ramazani, A. Rezaei, A.T. Mahyari, M. Rouhani, M. Khoobi,
 
Helvetica ChimicaActa, 2010, 93, 2033-2036.
[13] A. Souldozi, A. Ramazani, N. Bouslimani, R. Welter, Tetrahedron Letters, 2007, 48, 2617-2620.
[14] E. Ahmadi, A. Ramazani, M.N. Haghighi, Tetrahedron Letters, 2007, 48, 6954-6957.
[15] A. Ramazani, A. Rezaei, Organic letters, 2010, 12, 2852-2855.
[16] A. Ramazani, M. Rouhani, A. Rezaei, N. Shajari, A. Souldozi, Helvetica ChimicaActa, 2011, 94, 282-288.
[17] A. Massoudi, I. Amini, A. Ramazani, F.Z. NASRABADI, Turkish Journal of Chemistry, 2012, 36, 537-544.
[18] A. Ramazani, K. Dastanra, F.Z. Nasrabadi, Z. Karimi, M. Rouhani, M. Hosseini, Turkish Journal of Chemistry, 2012, 36, 467-476.
[19] A. Massoudi, I. Amini, A. Ramazani, Turkish Journal of Chemistry, 2012, 36, 779-787.
[20] A. Ramazani, S.W. Joo, F.Z. Nasrabadi, Turkish Journal of Chemistry, 2013, 37, 405-412.
[21] K.Y. Lee, J.M. Kim, J.N. Kim, Tetrahedron letters, 2003, 44, 6737-6740.
[22] J. Elguero, A. Katritzky, C. Rees, E. Scriven, Comprehensive Heterocyclic Chemistry II, 1996, 3, 11608-11618.
[23] N. Almirante, A. Cerri, G. Fedrizzi, G. Marazzi, M. Santagostino, Tetrahedron letters, 1998, 39, 3287-3290.
[24] M.J. Genin, C. Biles, B.J. Keiser, S.M. Poppe, S.M. Swaney, W.G. Tarpley, Y. Yagi, D.L. Romero, Journal of medicinal chemistry, 2000, 43, 1034-1040.
[25] Y.R. Huang, J.A. Katzenellenbogen, Organic letters, 2000, 2, 2833-2836.
[26] H. Cheng, Q.-Y.Wu, F. Han, G.-F.Yang, Chinese Chemical Letters, 2014, 25, 705-709.
[27] J. Greenhill, Comprehensive heterocyclic chemistry, 1984, 5, 302-325.
[28] J. Tang, L.M. Shewchuk, H. Sato, M. Hasegawa, Y. Washio, N. Nishigaki, Bioorganic & medicinal chemistry letters, 2003, 13, 2985-2988.
[29] F. Mohamed, L. Senarathna, A. Percy, M. Abeyewardene, G. Eaglesham, R. Cheng, S. Azher, A. Hittarage, W. Dissanayake, M.R. Sheriff, Clinical Toxicology, 2004, 42, 955-963.
[30] L. Ma’mani, A. Heydari, M. Sheykhan, Applied Catalysis A: General, 2010, 384, 122-127.
[31] S. Shylesh, V. Schünemann, W.R. Thiel, AngewandteChemie International Edition, 2010, 49, 3428-3459.
[32] H. Nagabhushana, S. SandeepSaundalkar, L. Muralidhar, B.M. Nagabhushana, C.R. Girija, D. Nagaraja, M.A. Pasha, V.P. Jayashankara, Chinese Chemical Letters, 2011, 22, 143-146.
[33] M. Mohsenimehr, M. Mamaghani, F. Shirini, M. Sheykhan, F.A. Moghaddam, Chinese Chemical Letters, 2014, 25, 1387-1391.
[34] S. Rostamizadeh, M. Nojavan, R. Aryan, E. Isapoor, M. Azad, Journal of Molecular Catalysis A: Chemical, 2013, 374-375, 102-110.
[35] S. Rostamnia, A. Nuri, H. Xin, A. Pourjavadi, S.H. Hosseini, Tetrahedron Letters, 2013, 54, 3344-3347.
[36] S. Sobhani, M. Bazrafshan, A.A. Delluei, Z.P. Parizi, Applied Catalysis A: General, 2013, 454, 145-151.
[37] Y. Wu, X. Wang, Materials Letters, 2011, 65, 2062-2065.
[38] M. Adib, B. Mohammadi, H.R. Bijanzadeh, Synlett, 2008, 3180-3182.
[39] M. Adib, B. Mohammadi, M. Mahdavi, A. Abbasi, M.R. Kesheh, Synlett, 2007, 2497-2500.
[40] M. Adib, B. Mohammadi, E. Sheikhi, H.R. Bijanzadeh, Chinese Chemical Letters, 2011, 22, 314-317.
[41] A. Ramazani, B. Mohammadi, N. Noshiranzadeh, Phosphorus, Sulfur, and Silicon and the Related Elements, 2003, 178, 545-548.
[42] A. Ramazani, N. Noshiranzadeh, B. Mohammadi, Phosphorus, Sulfur, and Silicon and the Related Elements, 2003, 178, 761-765.
[43] A. Ramazani, N. Noshiranzadeh, B. Mohammadi, Phosphorus, Sulfur, and Silicon and the Related Elements, 2003, 178, 539-543.
[44] A. Saeed, I. Arshad, U. Flörke, Crystals, 2012, 2, 1248-1252.
[45] I. Yavari, F. Nasiri, L. Moradi, H. Djahaniani, Tetrahedron Letters, 2004, 45, 7099-7101.