Novel acidic ChCl/TFA DES as reaction medium and catalyst for Biginelli and Hantzsch reactions
الموضوعات :
Iranian Journal of Catalysis
Adeleh Moshtaghi Zonouz
1
,
Abdolreza Abri
2
,
Nasrin babajani
3
,
Hemayat Shekaari
4
1 - Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz – Iran
2 - Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz – Iran
3 - Chemistry Department, Faculty of Science, Azarbaijan Shahid Madani University, Tabriz – Iran
4 - Faculty of Chemistry, Tabriz University, Tabriz – Iran
تاريخ الإرسال : 23 الخميس , جمادى الأولى, 1442
تاريخ التأكيد : 17 الجمعة , صفر, 1443
تاريخ الإصدار : 24 الأربعاء , محرم, 1443
الکلمات المفتاحية:
Biginelli reaction,
Choline chloride,
Hantzsch reaction,
Deep eutectic mixture,
Triflouroacetic acid,
ملخص المقالة :
Novel deep eutectic solvent (DES) using Choline Chloride (ChCl) as the hydrogen bond acceptor and triflouroacetic acid (TFA) as hydrogen bond donor (1.0:1.5 molar ratio) was prepared at room temperature and characterized by FT- IR and 1H NMR spectroscopy. Also, this novel acidic RTDES (room temperature deep eutectic solvent) was successfully used both as a reaction medium and catalyst in Biginelli, Biginelli-like, and Hantzsch reactions. The procedures have the advantages of high yields, short reaction times and easy work-up as well as relatively mild conditions and they do not require additional catalysts and organic solvents. The DES could be easily recycled without considerable loss of activity even after more than three cycles.
المصادر:
P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Chem. Commun. 1 (2003), 70−71.
L. Smith, A.P. Abbott, K.S. Ryder, Chem. Rev. 114 (2014), 11060-11082.
Reichardt, T. Welton, Solvents and solvent effects in organic chemistry, John Wiley & Sons, 2011
A. Wender, Nat. prod. rep. 31 (2014), 433-440
Biginelli, Eur. J. Org. Chem. 24 (1891), 2962-2967
Hantzsch, Eur. J. Org. Chem. 14 (1881), 1637-1638
Puripat, R. Ramozzi, M. Hatanaka, W. Parasuk, V. Parasuk, K. Morokuma, J. Org. Chem. 80 (2015), 6959-6967
Sharma, M. Gupta, Green Chem. 17 (2015), 1100-1106
Bakavoli, H. Eshghi, M. Rahimizadeh, M.R. Housaindokht, A. Mohammadi, H. Monhemi, Res. Chem. Intermed. 41 (2015), 3497-3505
J. Triggle, Cell. Mol. Neurobiol. 23 (2003), 293-303
Moshtaghi Z., S. Baradaran H., Synth. Commun. 38 (2008), 290-296
Sehout, R. Boulcina, B. Boumoud, T. Boumoud, A. Debache, Synth. Commun. 47 (2017), 1185-1191
Azuaje, C.R. Tubío, L. Escalante, M. Gómez, F. Guitián, A. Coelho, O. Caamaño, A. Gil, E. Sotelo, Appl. Catal. A, 530 (2017), 203-210
Pasinszki, M. Krebsz, G.G. Lajgut, T. Kocsis, L. Kótai, S. Kauthale, S. Tekale, R. Pawar, New J. Chem. 42 (2018), 1092-1098
Elhamifar, P. Badin, G. Karimipoor, J. Colloid Interface Sci. 499 (2017), 120-127
Zhang, X.-M. Ma, H.-X. Wei, X. Zhao, J. Luo, RSC Adv. 7 (2017), 53861-53870
Rouhani, A. Morsali, New J. Chem. 41 (2017), 15475-15484
Rafiee, S. Eavani, S. Rashidzadeh, M. Joshaghani, Inorg. Chim. Acta 362 (2009), 3555-3562
G. Dekamin, S. Ilkhanizadeh, Z. Latifidoost, H. Daemi, Z. Karimi, M. Barikani, RSC Adv. 4 (2014), 56658-56664
C. Rovnyak, K.S. Atwal, A. Hedberg, S.D. Kimball, S. Moreland, J.Z. Gougoutas, B.C. O'Reilly, J. Schwartz, M.F. Malley, J. Med. Chem. 35 (1992), 3254-3263
Mukhopadhyay, A. Datta, B.K. Banik, J. Heterocycl. Chem. 44 (2007), 979-981
Hazarkhani, B. Karimi, Synthesis 8 (2004), 1239-1242
Liang, X. Wang, J.-X. Wang, Z. Du, Tetrahedron 63 (2007), 1981-1986
Saha, J.N. Moorthy, J. Org. Chem. 76 (2010), 396-402
Zhang, X. Wang, Z. Li, W. Wu, J. Liu, H. Wu, S. Cui, K. Guo, RSC Adv. 4 (2014), 19710-19715
Sheykhan, A. Yahyazadeh, Z. Rahemizadeh, RSC Adv. 6 (2016), 34553-34563
Nagarajaiah, A. Mukhopadhyay, J.N. Moorthy, Tetrahedron Lett. 57 (2016), 5135-5149
Biginelli, P. Gazz, Chim. Ital. 23 (1893), 360-416
P. Baruah, S. Gadhwal, D. Prajapati, J.S. Sandhu, Chem. Lett. 31 (2002), 1038-1039
-T. Wang, L.-W. Xu, C.-G. Xia, H.-Q. Wang, Tetrahedron lett. 45 (2004), 7951-7953
Russowsky, E.V. Benvenutti, G.S. Roxo, F. Grasel, Lett. Org. Chem. 4 (2007), 39-42
Gopalakrishnan, P. Sureshkumar, J. Thanusu, V. Kanagarajan, M.R. Ezhilarasi, Lett. Org. Chem. 5 (2008), 142-147
Arfan, L. Paquin, J. Bazureau, Russ. J. Org. Chem. 43 (2007), 1058-1064
-S. Wang, J.-T. Li, Z.-P. Lin, Lett. Org. Chem. 3 (2006), 523-525
Safari, S. Gandomi-Ravandi, J. Mol. Catal. A: Chem. 373 (2013), 72-77
Wan, R. Yuan, H.h. Xu, C. Wang, J.l. Qi, H. Wu, J. Heterocycl. Chem. 51 (2014), E123–E128
R. Hajipour, Y. Ghayeb, N. Sheikhan, A.E. Ruoho, Synth. Commun. 41 (2011), 2226-2233
Z.D. Heirati, F. Shirini, A.F. Shojaei, RSC Adv. 6 (2016), 67072-67085
Javidi, M. Esmaeilpour, F.N. Dodeji, RSC Adv. 5 (2015), 308-315
Liu, B. Xu, Tetrahedron Lett. 59 (2018), 869-872
Fujita, I. Takahashi, M. Hayashi, J. Wang, K. Fuchibe, J. Ichikawa, Eur. J. Org. Chem. 2 (2017), 262-265
G. Andrews, R. Faizova, R.M. Denton, Nat. Commun. 8 (2017), 15913-15919
M. Hosseini, E. Kolvari, N. Koukabi, M. Ziyaei, M.A. Zolfigol, Catal. Lett. 146 (2016), 1040-1049
M. El-Saghier, E.A. Ahmed, A.M. Mahmoud, J. Pharm. Appl. Chem. 1 (2015), 9-19
Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50 (2009), 5248-5250
P. Reddy, S. Sarveswari, V. Vijayakumar, Res. Chem. Intermed. 41 (2015), 6877-6883
Hong, C. Cai, W.-B. Yi, J. Fluor. Chem. 131 (2010), 111-114
-M. Ren, J.-J. Shao, Z.-C. Wu, M.-D. Xu, Org. Prep. Proced. Int. 46 (2014), 545-550
H. Nia, M. Mamaghani, F. Shirini, K. Tabatabaeian, M. Heidary, Org. Prep. Proced. Int. 46 (2014), 152-163
A. Navarro, C.A. Sierra, C. Ochoa-Puentes, RSC Adv. 6 (2016), 65355-65365
Moeinpour, A. Khojastehnezhad, E- J. Chem. 9 (2012), 504-509
Bednarz, M. Fluder, M. Galica, D. Bogdal, I. Maciejaszek, J. Appl. Polym. Sci. 131 (2014), 40608-40612
Shirini, M.A. Zolfigol, A. Abri, J. Iran. Chem. Soc., 5 (2008), 96-99.
M. Amini, A. Shaabani, A. Bazgir, catalysis. 7 (2006), 843-847.
Abri, M.G. Khojasteh, Lett. Org. Chem., (2017), 172-180
Valizadeh, A. Shockravi, Heteroat. Chem. 20 (2009), 284-288.
S. Yadav, B.V.S. Reddy, P. Sridhar, J.S.S. Reddy, K. Nagaiah, N.Lingaiah, P.S. Saiprasad, Eur. J. Org. Chem. 3 (2004), 552-557.
Ghosh, S. Maiti, A. Chakraborty, J. Mol. Catal. A Chem. 217 (2004), 47-50.