Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Preparation and Characterization of a Novel Glycine-based Ionic Liquid and its Application in the Synthesis of Xanthenediones and Dihydropyrimidones in Water

Author(s): Masoumeh Salami and Ali Ezabadi*

Volume 19, Issue 12, 2022

Published on: 05 August, 2022

Page: [1047 - 1061] Pages: 15

DOI: 10.2174/1570178619666220324122621

Price: $65

Abstract

Aim and Objective: A novel amino acid ionic liquid was synthesized, characterized, and approved as an efficient and recyclable catalyst for synthesizing xanthenediones and DHPMs in water at reflux temperature.

Materials and Methods: The ionic liquid was synthesized by a two-step method. In the first step, pyridine- N-sulfonic acid was prepared by the reaction of pyridine with chlorosulfonic acid. In the second step, the reaction of as-prepared ionic liquid with glycine in water afforded the desired amino acid ionic liquid. Then, the ionic liquid was fully characterized by FT-IR, 1H NMR, 13C NMR, MS, TG/DTG, and Hammett acidity function.

Results: We disclose a new strategy to incorporate glycine as the amino acid-based cation in the ionic liquid structure. The prepared IL exhibited remarkable catalytic activity in synthesizing xanthendiones and DHPMs in water at reflux temperature.

Conclusion: We have developed a green and efficient amino acid ionic liquid to synthesize xanthenediones in water at reflux temperature. The advantage of this protocol is highlighted by the novelty of the ionic liquid, using H2O as the solvent, simple work-up, high yields, and short reaction times.

Keywords: Amino acid ionic liquid, glycine, water, xanthenediones, DHPMS, reflux temperature.

Next »
Graphical Abstract

[1]
Vafaeezadeh, M.; Alinezhad, H. J. Mol. Liq., 2016, 218, 95-105.
[http://dx.doi.org/10.1016/j.molliq.2016.02.017]
[2]
Kumar, P.S.V.; Suresh, L.; Bhargavi, G.; Basavoju, S.; Chandramouli, G. ACS Sustain. Chem.& Eng., 2015, 3(11), 2944-2950.
[http://dx.doi.org/10.1021/acssuschemeng.5b00900]
[3]
Liu, H.; Yu, H. J. Mater. Sci. Technol., 2018, 35(4), 674-686.
[http://dx.doi.org/10.1016/j.jmst.2018.10.007]
[4]
Wu, C.; Zhang, H.; Yu, B.; Chen, Y.; Ke, Z.; Guo, S.; Liu, Z. ACS Catal., 2017, 7(11), 7772-7776.
[http://dx.doi.org/10.1021/acscatal.7b02231]
[5]
Zhang, W-H.; Shen, J-J.; Wu, J.; Liang, X-Y.; Xu, J.; Liu, P.; Xue, B.; Li, Y-X. Mol. Catal., 2017, 443, 262-269.
[http://dx.doi.org/10.1016/j.mcat.2017.10.018]
[6]
Davarpanah, J.; Kiasat, A.R. Technology (Singap.), 2017, 8, 12.
[7]
Kukawka, R.; Pawlowska-Zygarowicz, A.; Dzialkowska, J.; Pietrowski, M.; Maciejewski, H.; Bica, K.; Smiglak, M. ACS Sustain. Chem.& Eng., 2019, 7(5), 4699-4706.
[http://dx.doi.org/10.1021/acssuschemeng.8b04357]
[8]
Sadjadi, S.; Heravi, M.M.; Raja, M. Int. J. Biol. Macromol., 2019, 122, 228-237.
[http://dx.doi.org/10.1016/j.ijbiomac.2018.10.160] [PMID: 30393138]
[9]
Zhao, Q.; Zhao, X.; Peng, H.; Liu, Y.; Yang, L.; Sun, J.; Yang, L.; Shen, Y. Catal. Sci. Technol., 2019, 9(13), 3445-3453.
[http://dx.doi.org/10.1039/C9CY00620F]
[10]
Vekariya, R.L. J. Mol. Liq., 2017, 227, 44-60.
[http://dx.doi.org/10.1016/j.molliq.2016.11.123]
[11]
Javed, F.; Ullah, F.; Zakaria, M.R.; Akil, H.M. J. Mol. Liq., 2018, 271, 403-420.
[http://dx.doi.org/10.1016/j.molliq.2018.09.005]
[12]
Reddy, P.N.; Padmaja, P.; Reddy, B.V.S.; Rambabu, G. RSC Advances, 2015, 5(63), 51035-51054.
[http://dx.doi.org/10.1039/C5RA08625F]
[13]
Han, H-Y.; Geng, X.; Zhang, B-X.; Meng, J.; Liu, X.; He, X-M.; Liu, Z-G.; Gao, Y-F.; Liu, D.; Hu, X-M. RSC Advances, 2019, 9(51), 29652-29658.
[http://dx.doi.org/10.1039/C9RA06243B]
[14]
Lei, Y.; Yu, L.; Shen, M.; Luo, S.; Gao, Z. New J. Chem., 2019, 43, 15700-15705.
[http://dx.doi.org/10.1039/C9NJ02581B]
[15]
Pereira, V.A.; Mendonça, P.V.; Coelho, J.F.; Serra, A.C. Polym. Chem., 2019, 10(36), 4904-4913.
[http://dx.doi.org/10.1039/C9PY00865A]
[16]
Hirose, D.; Kusuma, S.B.W.; Ina, D.; Wada, N.; Takahashi, K. Green Chem., 2019, 21(18), 4927-4931.
[http://dx.doi.org/10.1039/C9GC01333D]
[17]
Peris, E.; Porcar, R.; Burguete, M.I.; García‐Verdugo, E.; Luis, S.V. ChemCatChem, 2019, 11(7), 1955-1962.
[http://dx.doi.org/10.1002/cctc.201900086]
[18]
Chen, F.F.; Huang, K.; Zhou, Y.; Tian, Z.Q.; Zhu, X.; Tao, D.J.; Jiang, D.E.; Dai, S. Angew. Chem. Int. Ed. Engl., 2016, 55(25), 7166-7170.
[http://dx.doi.org/10.1002/anie.201602919] [PMID: 27136274]
[19]
Chen, F.F.; Huang, K.; Fan, J.P.; Tao, D.J. AIChE J., 2018, 64(2), 632-639.
[http://dx.doi.org/10.1002/aic.15952]
[20]
Ossowicz, P.; Rozwadowski, Z.; Gano, M.; Janus, E. Pol. J. Chem. Technol., 2016, 18(4), 90-95.
[http://dx.doi.org/10.1515/pjct-2016-0076]
[21]
Fukumoto, K.; Yoshizawa, M.; Ohno, H. J. Am. Chem. Soc., 2005, 127(8), 2398-2399.
[http://dx.doi.org/10.1021/ja043451i] [PMID: 15724987]
[22]
Song, Z.; Liang, Y.; Fan, M.; Zhou, F.; Liu, W. RSC Advances, 2014, 4(37), 19396-19402.
[http://dx.doi.org/10.1039/c3ra47644h]
[23]
Mu, L.; Shi, Y.; Guo, X.; Ji, T.; Chen, L.; Yuan, R.; Brisbin, L.; Wang, H.; Zhu, J. RSC Advances, 2015, 5(81), 66067-66072.
[http://dx.doi.org/10.1039/C5RA11093A]
[24]
Karthikeyan, P.; Kumar, S.S.; Arunrao, A.S.; Narayan, M.P.; Bhagat, P.R. Res. Chem. Intermed., 2013, 39(3), 1335-1342.
[http://dx.doi.org/10.1007/s11164-012-0689-4]
[25]
Azarifar, D.; Badalkhani, O.; Abbasi, Y. Appl. Organomet. Chem., 2018, 32(1), e3949.
[http://dx.doi.org/10.1002/aoc.3949]
[26]
Khodamorady, M.; Sohrabnezhad, S.; Bahrami, K. Polyhedron, 2020, 178, 114340.
[http://dx.doi.org/10.1016/j.poly.2019.114340]
[27]
Singh, M.S.; Nagaraju, A.; Verma, G.K.; Shukla, G.; Verma, R.K.; Srivastava, A.; Raghuvanshi, K. Green Chem., 2013, 15(4), 954-962.
[http://dx.doi.org/10.1039/c3gc37047j]
[28]
Kumar, R.; Raghuvanshi, K.; Verma, R.K.; Singh, M.S. Tetrahedron Lett., 2010, 51(45), 5933-5936.
[http://dx.doi.org/10.1016/j.tetlet.2010.09.017]
[29]
Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem., 2000, 65(12), 3864-3868.
[http://dx.doi.org/10.1021/jo9919052] [PMID: 10864778]
[30]
Maleki, A.; Zand, P.; Mohseni, Z. ChemistrySelect, 2017, 2(9), 2740-2744.
[http://dx.doi.org/10.1002/slct.201700131]
[31]
Kariya, V.H.; Mulani, V.; Savant, M.M. Res.J.Chem.Sci., 2017, 7, 63-65.
[32]
Devthade, V.; Kamble, G.; Ghugal, S.G.; Chikhalia, K.H.; Umare, S.S. ChemistrySelect, 2018, 3(14), 4009-4014.
[http://dx.doi.org/10.1002/slct.201800591]
[33]
Kolosov, M.A.; Kulyk, O.G.; Al-Ogaili, M.J.; Orlov, V.D. Tetrahedron Lett., 2015, 56(32), 4666-4669.
[http://dx.doi.org/10.1016/j.tetlet.2015.06.041]
[34]
Khatri, C.K.; Rekunge, D.S.; Chaturbhuj, G.U. New J. Chem., 2016, 40(12), 10412-10417.
[http://dx.doi.org/10.1039/C6NJ03120J]
[35]
He, L.; Qin, S.; Liu, J.; Zhao, W.; Chang, T. World J. Eng., 2020, 17, 21-26.
[http://dx.doi.org/10.1108/WJE-09-2019-0255]
[36]
Hideo, T.; Teruomi, J. Chem. Abstr., 1981, 95, 80922b.
[37]
Poupelin, J.P.; Saint-Ruf, G.; Foussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lacroix, R. Eur. J. Med. Chem., 1978, 13, 67.
[38]
Lambert, R.W.; Martin, J.A.; Merrett, J.H.; Parkes, K.E.B.; Thomas, G.J. Chem. Abstr., 1997, 126, 212377y.
[39]
Saint-Ruf, G. Huynh-Trong-Hieu; Poupelin, J.P. Naturwissenschaften, 1975, 62(12), 584-585.
[http://dx.doi.org/10.1007/BF01166986] [PMID: 1214868]
[40]
Ion, R.M.; Planner, A.; Wiktorowicz, K.; Frackowiak, D. Acta Biochim. Pol., 1998, 45(3), 833-845.
[http://dx.doi.org/10.18388/abp.1998_4279] [PMID: 9918512]
[41]
Shirini, F.; Khaligh, N.G. Dyes Pigm., 2012, 95(3), 789-794.
[http://dx.doi.org/10.1016/j.dyepig.2012.06.022]
[42]
Lue, H.Y.; Li, J.J.; Zhang, Z.H. Appl. Organomet. Chem., 2009, 23(4), 165.
[http://dx.doi.org/10.1002/aoc.1488]
[43]
Zhou, Z.; Deng, X. J. Mol. Catal. Chem., 2013, 367, 99.
[http://dx.doi.org/10.1016/j.molcata.2012.11.002]
[44]
Maleki, B.; Davoodi, A.; Azghandi, M.V.; Baghayeri, M.; Akbarzadeh, E.; Veisi, H.; Ashrafi, S.S.; Raei, M. New J. Chem., 2016, 40(2), 1278-1286.
[http://dx.doi.org/10.1039/C5NJ02707A]
[45]
Das, P.J.; Das, J. RSC Advances, 2015, 5(16), 11745-11752.
[http://dx.doi.org/10.1039/C4RA12298D]
[46]
Ilangovan, A.; Malayappasamy, S.; Muralidharan, S.; Maruthamuthu, S. Chem. Cent. J., 2011, 5(1), 81.
[http://dx.doi.org/10.1186/1752-153X-5-81] [PMID: 22152051]
[47]
Dadhania, A.N.; Patel, V.K.; Raval, D.K. J. Saudi Chem. Soc., 2017, 21, S163-S169.
[http://dx.doi.org/10.1016/j.jscs.2013.12.003]
[48]
Zhang, Z-H.; Liu, Y-H. Catal. Commun., 2008, 9(8), 1715.
[http://dx.doi.org/10.1016/j.catcom.2008.01.031]
[49]
Venkatesan, K.; Pujari, S.S.; Lahoti, R.J.; Srinivasan, K.V. Ultrason. Sonochem., 2008, 15(4), 548-553.
[http://dx.doi.org/10.1016/j.ultsonch.2007.06.001] [PMID: 17658286]
[50]
Azizi, N.; Abbasi, F.; Abdoli‐Senejani, M. ChemistrySelect, 2018, 3(13), 3797.
[http://dx.doi.org/10.1002/slct.201800138]
[51]
Amoozadeh, A.; Hosseininya, S.F.; Rahmani, S. Res. Chem. Intermed., 2018, 44(2), 991-1011.
[http://dx.doi.org/10.1007/s11164-017-3148-4]
[52]
Abbasi, F.; Azizi, N.; Abdoli-Senejani, M. J. Iran. Chem. Soc., 2017, 14(10), 2097-2103.
[http://dx.doi.org/10.1007/s13738-017-1146-5]
[53]
Banakar, S.H.; Dekamin, M.G.; Yaghoubi, A. New J. Chem., 2018, 42(17), 14246-14262.
[http://dx.doi.org/10.1039/C8NJ01053F]
[54]
Tajfirooz, F.; Davoodnia, A.; Pordel, M.; Ebrahimi, M.; Khojastehnezhad, A. Appl. Organomet. Chem., 2018, 32(1), e3930.
[http://dx.doi.org/10.1002/aoc.3930]
[55]
Hazeri, N.; Masoumnia, A.; Mghsoodlou, M.T.; Salahi, S.; Kangani, M.; Kianpour, S.; Kiaee, S.; Abonajmi, J. Res. Chem. Intermed., 2015, 41(7), 4123.
[http://dx.doi.org/10.1007/s11164-013-1516-2]
[56]
Rajabi, F.; Pinilla-de Dios, M.; Abdollahi, M.; Luque, R. Catal. Commun., 2019, 120, 95-100.
[http://dx.doi.org/10.1016/j.catcom.2018.10.004]
[57]
Sahebi, H.; Konoz, E.; Ezabadi, A. New J. Chem., 2019, 43(34), 13554-13570.
[http://dx.doi.org/10.1039/C9NJ02200G]
[58]
Salami, M.; Ezabadi, A. Res. Chem. Intermed., 2019, 45(7), 3673.
[http://dx.doi.org/10.1007/s11164-019-03814-3]
[59]
Abdi Piralghar, Z.; Hashemi, M.M.; Ezabadi, A. Polycycl. Aromat. Compd., 2019, 1.
[http://dx.doi.org/10.1080/10406638.2018.1557709]
[60]
Ehsani-Nasab, Z.; Ezabadi, A. Comb. Chem. High Throughput Screen., 2018, 21(8), 602-608.
[http://dx.doi.org/10.2174/1386207321666181106114848] [PMID: 30398113]
[61]
Piralghar, Z.A.; Hashemi, M.M.; Ezabadi, A. Comb. Chem. High Throughput Screen., 2018, 21(7), 526-532.
[http://dx.doi.org/10.2174/1386207321666180828092546] [PMID: 30152280]
[62]
Moosavi-Zare, A.R.; Zolfigol, M.A.; Zarei, M.; Zare, A.; Khakyzadeh, V. J. Mol. Liq., 2013, 186, 63-69.
[http://dx.doi.org/10.1016/j.molliq.2013.05.009]
[63]
Sabaqian, S.; Nemati, F.; Nahzomi, H.T.; Heravi, M.M. Carbohydr. Polym., 2017, 177, 165-177.
[http://dx.doi.org/10.1016/j.carbpol.2017.08.109] [PMID: 28962755]
[64]
Karimi-Jaberi, Z.; Moaddeli, M.S. ISRN Org. Chem., 2012, 2012, 474626.
[65]
Shirini, F.; Yahyazadeh, A.; Mohammadi, K. Chin. Chem. Lett., 2014, 25(2), 341-347.
[http://dx.doi.org/10.1016/j.cclet.2013.11.016]
[66]
Masri, A.N.; Mutalib, M.A.; Aminuddin, N.F.; Lévêque, J.M. Separ. Purif. Tech., 2018, 196, 106-114.
[http://dx.doi.org/10.1016/j.seppur.2017.08.061]
[67]
Shirini, F.; Langarudi, M.S.N.; Seddighi, M.; Jolodar, O.G. Res. Chem. Intermed., 2015, 41(11), 8483-8497.
[http://dx.doi.org/10.1007/s11164-014-1905-1]
[68]
Moosavi-Zare, A.R.; Zolfigol, M.A.; Zarei, M.; Zare, A.; Khakyzadeh, V.; Hasaninejad, A. Appl. Catal., 2013, 467, 61-68.
[69]
Nisar, M.; Ali, I.; Shah, M.R.; Badshah, A.; Qayum, M.; Khan, H.; Khan, I.; Ali, S. RSC Advances, 2013, 3(44), 21753.
[http://dx.doi.org/10.1039/c3ra43506g]
[70]
Sharma, N.; Sharma, U.K.; Kumar, R. Richa, Sinha, A. K. RSC Advances, 2012, 2(28), 10648-10651.
[71]
Li, M.; Guo, W-S.; Wen, L-R.; Li, Y-F.; Yang, H-Z. J. Mol. Catal. Chem., 2006, 258(1-2), 133-138.
[http://dx.doi.org/10.1016/j.molcata.2006.05.028]
[72]
Zhang, H.; Li, H.; Liu, C. J. Org. Chem. Res., 2018, 6(02), 61.
[http://dx.doi.org/10.12677/JOCR.2018.62010]
[73]
Elhamifar, D.; Shábani, A. Chemistry, 2014, 20(11), 3212-3217.
[http://dx.doi.org/10.1002/chem.201304349] [PMID: 24519957]
[74]
Jain, S.L.; Joseph, J.K.; Sain, B. Catal. Lett., 2007, 115(1-2), 52-55.
[http://dx.doi.org/10.1007/s10562-007-9070-4]
[75]
Sudhan, P.N.; Ghashang, M.; Mansoor, S.S. J. Saudi Chem. Soc., 2017, 21(7), 776-786.
[http://dx.doi.org/10.1016/j.jscs.2015.09.005]

Rights & Permissions Print Cite
Article Metrics
8
© 2024 Bentham Science Publishers | Privacy Policy