﻿<?xml version="1.0" encoding="utf-8" ?>
<XML>
  <ISCJOURNAL>
    <YEAR>2022</YEAR>
    <VOL>4</VOL>
    <NO>12</NO>
    <MOSALSAL>12</MOSALSAL>
    <PAGE_NO>5</PAGE_NO>
    <ARTICLES>
      <ARTICLE>
        <LANGUAGE_ID>1</LANGUAGE_ID>
        <TitleF/>
        <TitleE>Choline chloride based eutectic solvent: a highly efficient reaction media for the synthesis of 3,4-dihydropyrimidin-2(1H)-thiones</TitleE>
        <URL>https://jourcc.com/index.php/jourcc/article/view/jcc434</URL>
        <DOI>10.52547/jcc.4.3.4</DOI>
        <ABSTRACTS>
          <ABSTRACT>
            <LANGUAGE_ID>1</LANGUAGE_ID>
            <CONTENT>A mild and green protocol was developed to the 3,4-dihydropyrimidin-2(1H)-thione derivatives preparation in deep eutectic solvent without the use of a catalyst or any other additive. The procedure offers a number of benefits, including clean reaction profile, avoiding the use of typical toxic catalysts, an easy workup procedure, short reaction times, and low prices.</CONTENT>
          </ABSTRACT>
        </ABSTRACTS>
        <PAGES>
          <PAGE>
            <FPAGE>153</FPAGE>
            <TPAGE>157</TPAGE>
          </PAGE>
        </PAGES>
        <AUTHORS>
          <AUTHOR>
            <Name/>
            <MidName/>
            <Family/>
            <NameE>Fatemeh</NameE>
            <MidNameE/>
            <FamilyE>Malamiri</FamilyE>
            <Organizations>
              <Organization>Ahvaz Branch, Islamic Azad University (IAU)</Organization>
            </Organizations>
            <Countries>
              <Country>Iran</Country>
            </Countries>
            <EMAILS>
              <Email>info@jourcc.com</Email>
            </EMAILS>
          </AUTHOR>
          <AUTHOR>
            <Name/>
            <MidName/>
            <Family/>
            <NameE>Rashid</NameE>
            <MidNameE/>
            <FamilyE>Badri</FamilyE>
            <Organizations>
              <Organization>Ahvaz Branch, Islamic Azad University (IAU)</Organization>
            </Organizations>
            <Countries>
              <Country>Iran</Country>
            </Countries>
            <EMAILS>
              <Email>info@jourcc.com</Email>
            </EMAILS>
          </AUTHOR>
          <AUTHOR>
            <NameE>Samad</NameE>
            <MidNameE/>
            <FamilyE>Khaksar</FamilyE>
            <Organizations>
              <Organization>Ayatollah Amoli Branch, Islamic Azad University (IAU)</Organization>
            </Organizations>
            <Countries>
              <Country>Iran</Country>
            </Countries>
            <Organizations>
              <Organization>Ayatollah Amoli Branch, Islamic Azad University (IAU)</Organization>
              <Organization>The University of Georgia</Organization>
            </Organizations>
            <Countries>
              <Country>Georgia</Country>
              <Country>Iran</Country>
            </Countries>
            <EMAILS>
              <Email>s.khaksar@ug.edu.ge</Email>
            </EMAILS>
          </AUTHOR>
          <AUTHOR>
            <Name/>
            <MidName/>
            <Family/>
            <NameE>Peyman</NameE>
            <MidNameE/>
            <FamilyE>Salahshour</FamilyE>
            <Organizations>
              <Organization>The University of Georgia</Organization>
            </Organizations>
            <Countries>
              <Country>Georgia</Country>
            </Countries>
            <EMAILS>
              <Email>info@jourcc.com</Email>
            </EMAILS>
          </AUTHOR>
        </AUTHORS>
        <KEYWORDS>
          <KEYWORD>
            <KeyText>Deep Eutectic Solvent</KeyText>
          </KEYWORD>
          <KEYWORD>
            <KeyText>Green solvent</KeyText>
          </KEYWORD>
          <KEYWORD>
            <KeyText>Dihydropyrimidine</KeyText>
          </KEYWORD>
          <KEYWORD>
            <KeyText>Multicomponent</KeyText>
          </KEYWORD>
          <KEYWORD>
            <KeyText>Biginelli condensation</KeyText>
          </KEYWORD>
        </KEYWORDS>
        <PDFFileName>Article4.pdf</PDFFileName>
        <REFRENCES>
          <REFRENCE>
            <REF>[1] P. Liu, J.-W. Hao, L.-P. Mo, Z.-H. Zhang, Recent advances in the application of deep eutectic solvents as sustainable media as well as catalysts in organic reactions, RSC Advances 5(60) (2015) 48675-48704.##[2] C. Ruß, B. König, Low melting mixtures in organic synthesis–an alternative to ionic liquids?, Green Chemistry 14(11) (2012) 2969-2982.##[3] Q. Zhang, K.D.O. Vigier, S. Royer, F. Jerome, Deep eutectic solvents: syntheses, properties and applications, Chemical Society Reviews 41(21) (2012) 7108-7146.##[4] Y. Yu, X. Lu, Q. Zhou, K. Dong, H. Yao, S. Zhang, Biodegradable naphthenic acid ionic liquids: synthesis, characterization, and quantitative structure–biodegradation relationship, Chemistry–A European Journal 14(35) (2008) 11174-11182.##[5] K.D. Weaver, H.J. Kim, J. Sun, D.R. MacFarlane, G.D. Elliott, Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications, Green Chemistry 12(3) (2010) 507-513.##[6] S.K. Ghosh, R. Nagarajan, Deep eutectic solvent mediated synthesis of quinazolinones and dihydroquinazolinones: synthesis of natural products and drugs, RSC Advances 6(33) (2016) 27378-27387.##[7] P.M. Pawar, K.J. Jarag, G.S. Shankarling, Environmentally benign and energy efficient methodology for condensation: an interesting facet to the classical Perkin reaction, Green Chemistry 13(8) (2011) 2130-2134.##[8] G. Imperato, E. Eibler, J. Niedermaier, B. König, Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions, Chemical Communications (9) (2005) 1170-1172.##[9] F. Ilgen, B. König, Organic reactions in low melting mixtures based on carbohydrates and L-carnitine—a comparison, Green Chemistry 11(6) (2009) 848-854.##[10] G. Imperato, S. Höger, D. Lenoir, B. Koenig, Low melting sugar–urea–salt mixtures as solvents for organic reactions—estimation of polarity and use in catalysis, Green Chemistry 8(12) (2006) 1051-1055.##[11] U.B. Patil, A.S. Singh, J.M. Nagarkar, Choline chloride based eutectic solvent: an efficient and reusable solvent system for the synthesis of primary amides from aldehydes and from nitriles, RSC Advances 4(3) (2014) 1102-1106.##[12] A. Shaabani, S.E. Hooshmand, M.T. Nazeri, R. Afshari, S. Ghasemi, Deep eutectic solvent as a highly efficient reaction media for the one-pot synthesis of benzo-fused seven-membered heterocycles, Tetrahedron Letters 57(33) (2016) 3727-3730.##[13] S. Gore, S. Baskaran, B. Koenig, Efficient synthesis of 3, 4-dihydropyrimidin-2-ones in low melting tartaric acid–urea mixtures, Green Chemistry 13(4) (2011) 1009-1013.##[14] Y. Dai, J. van Spronsen, G.-J. Witkamp, R. Verpoorte, Y.H. Choi, Ionic liquids and deep eutectic solvents in natural products research: mixtures of solids as extraction solvents, Journal of natural products 76(11) (2013) 2162-2173.##[15] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Novel solvent properties of choline chloride/urea mixtures, Chemical Communications (1) (2003) 70-71.##[16] R. Gautam, N. Kumar, J.G. Lynam, Theoretical and experimental study of choline chloride-carboxylic acid deep eutectic solvents and their hydrogen bonds, Journal of Molecular Structure 1222 (2020) 128849.##[17] P. Biginelli, Aldehyde-urea derivatives of aceto-and oxaloacetic acids, Gazz. chim. ital 23(1) (1893) 360-413.##[18] M. Karimi, E. Sadeghi, S.K. Bigdeli, M. Zahedifar, Synthesis, feasibility study of production of singlet oxygen and hydroxyl radical and performance in antibacterial activity of ZnS: Eu QDs, Journal of Composites and Compounds 4(11) (2022) 77-82.##[19] R. Kaur, S. Chaudhary, K. Kumar, M.K. Gupta, R.K. Rawal, Recent synthetic and medicinal perspectives of dihydropyrimidinones: A review, European journal of medicinal chemistry 132 (2017) 108-134.##[20] A.H. Saleh, D. Kumar, I. Sirakov, P. Shafiee, M. Arefian, Application of nano compounds for the prevention, diagnosis, and treatment of SARS-coronavirus: A review, Journal of Composites and Compounds 3(9) (2021) 230-246.##[21] A. Bakhtiari, A. Cheshmi, M. Naeimi, S.M. Fathabad, M. Aliasghari, A.M. Chahardehi, S. Hassani, V. Elhami, Synthesis and characterization of the novel 80S bioactive glass: bioactivity, biocompatibility, cytotoxicity, Journal of Composites and Compounds 2(4) (2020) 110-114.##[22] H. Murata, H. Ishitani, M. Iwamoto, Synthesis of Biginelli dihydropyrimidinone derivatives with various substituents on aluminium-planted mesoporous silica catalyst, Organic and biomolecular chemistry 8(5) (2010) 1202-1211.##[23] T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, T.J. Mitchison, Small molecule inhibitor of mitotic spindle bipolarity identified in a phenotype-based screen, Science 286(5441) (1999) 971-974.##[24] D. Russowsky, R.m.F. Canto, S.A. Sanches, M.G. D’Oca, Â. de Fátima, R.A. Pilli, L.K. Kohn, M.A. Antoˆnio, J.E. de Carvalho, Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: monastrol, oxo-monastrol and oxygenated analogues, Bioorganic chemistry 34(4) (2006) 173-182.##[25] R.S. Chang, T.-B. Chen, S.S. O'Malley, D.J. Pettibone, J. DiSalvo, B. Francis, M.G. Bock, R. Freidinger, D. Nagarathnam, S.W. Miao, In vitro studies on L-771,688 (SNAP 6383), a new potent and selective α1A-adrenoceptor antagonist, European journal of pharmacology 409(3) (2000) 301-312.##[26] K.S. Atwal, B.N. Swanson, S.E. Unger, D.M. Floyd, S. Moreland, A. Hedberg, B.C. O'Reilly, Dihydropyrimidine calcium channel blockers. 3. 3-Carbamoyl-4-aryl-1, 2, 3, 4-tetrahydro-6-methyl-5-pyrimidinecarboxylic acid esters as orally effective antihypertensive agents, Journal of medicinal chemistry 34(2) (1991) 806-811.##[27] R.N. Azadani, M. Sabbagh, H. Salehi, A. Cheshmi, A. Raza, B. Kumari, G. Erabi, Sol-gel: Uncomplicated, routine and affordable synthesis procedure for utilization of composites in drug delivery, Journal of Composites and Compounds 3(6) (2021) 57-70.##[28] P. Fazlali, A. Mahdian, M.S. Soheilifar, S.M. Amininasab, P. Shafiee, I.A. Wani, A.M.A.A. AL-Mokaram, Nanobiosensors for early detection of neurodegenerative disease, Journal of Composites and Compounds 4(10) (2022) 24-36.##[29] P. Biginelli, Aldureides of ethylic acetoacetate and ethylic oxalacetate, Gazz. Chim. Ital 23 (1893) 360-416.##[30] V.P.S. Sidhu, R. Borges, M. Yusuf, S. Mahmoudi, S.F. Ghorbani, M. Hosseinikia, P. Salahshour, F. Sadeghi, M. Arefian, A comprehensive review of bioactive glass: synthesis, ion substitution, application, challenges, and future perspectives, Journal of Composites and Compounds 3(9) (2021) 247-261.##[31] S. Padervand, M. Amiri, Optimization of electrolyte concentration for surface modification of tantalum using plasma electrolytic nitridation, International Journal of Refractory Metals and Hard Materials 87 (2020) 105146.##[32] S. Askari, M. Ghashang, G. Sohrabi, Synthesis and mechanical properties of Bi2O3-Al4Bi2O9 nanopowders, Journal of Composites and Compounds 2(5) (2020) 171-174.##[33] P. Shafiee, M.R. Nafchi, S. Eskandarinezhad, S. Mahmoudi, E. Ahmadi, Sol-gel zinc oxide nanoparticles: advances in synthesis and applications, Synthesis and Sintering 1(4) (2021) 242-254.##[34] N. Ahmed, Z.N. Siddiqui, Sulphated silica tungstic acid as a highly efficient and recyclable solid acid catalyst for the synthesis of tetrahydropyrimidines and dihydropyrimidines, Journal of Molecular Catalysis A: Chemical 387 (2014) 45-56.##[35] S.D. Salim, K.G. Akamanchi, Sulfated tungstate: an alternative, eco-friendly catalyst for Biginelli reaction, Catalysis Communications 12(12) (2011) 1153-1156.##[36] C.K. Khatri, D.S. Rekunge, G.U. Chaturbhuj, Sulfated polyborate: a new and eco-friendly catalyst for one-pot multi-component synthesis of 3, 4-dihydropyrimidin-2 (1 H)-ones/thiones via Biginelli reaction, New Journal of Chemistry 40(12) (2016) 10412-10417.##[37] S. Khaksar, S.M. Vahdat, R.N. Moghaddamnejad, Pentafluorophenylammonium triflate: an efficient, practical, and cost-effective organocatalyst for the Biginelli reaction, Monatshefte für Chemie-Chemical Monthly 143(12) (2012) 1671-1674.##[38] O.M. Singh, M.L. Singh, S.J. Singh, SNCL2-CATALYZED SYNTHESIS OF DIHYDROPYRIMIDINONES UNDER SOLVENT-FREE CONDITIONS, Heterocyclic Communications 13(5) (2007) 277-282.##[39] J. Safari, S. Gandomi-Ravandi, S. Ashiri, Organosilane sulfonated graphene oxide in the Biginelli and Biginelli-like reactions, New Journal of Chemistry 40(1) (2016) 512-520.##[40] S. Nagarajan, T.M. Shaikh, E. Kandasamy, Synthesis of 1-alkyl triazolium triflate room temperature ionic liquids and their catalytic studies in multi-component Biginelli reaction, Journal of Chemical Sciences 127(9) (2015) 1539-1545.##[41] Q. Liu, N. Pan, J. Xu, W. Zhang, F. Kong, Microwave-assisted and iodine-catalyzed synthesis of dihydropyrimidin-2-thiones via biginelli reaction under solvent-free conditions, Synthetic Communications 43(1) (2013) 139-146.##[42] D. Bhuyan, M. Saikia, L. Saikia, ZnO nanoparticles embedded in SBA-15 as an efficient heterogeneous catalyst for the synthesis of dihydropyrimidinones via Biginelli condensation reaction, Microporous and Mesoporous Materials 256 (2018) 39-48.##[43] M. Moghaddas, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, Sulfonated carbon catalyzed Biginelli reaction for one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones and-thiones, Chinese Journal of Catalysis 33(4-6) (2012) 706-710.##[44] S. Padervand, S. Sarihi, S. Mousavi Khoei, N. Shakiba, Determining the Optimal Processing Time for Tantalum Surface Modification through Plasma Electrolytic Nitridation, Journal of Surface Investigation: X-ray, Synchrotron and Neutron Techniques 15(4) (2021) 877-884.##[45] S. Padervand, S. Khoei, N. Shakiba, Access to Optimum Working Voltage of Plasma Electrolytic Nitridation of Tantalum Alloys, Surface Engineering and Applied Electrochemistry 56(6) (2020) 704-711.##[46] N. Aboualigaledari, M. Rahmani, A review on the synthesis of the TiO2-based photocatalyst for the environmental purification, Journal of Composites and Compounds 3(6) (2021) 25-42.##[47] A.J. Rad, Synthesis of copper oxide nanoparticles on activated carbon for pollutant removal in Tartrazine structure, Journal of Composites and Compounds 2(3) (2020) 99-104.##[48] E.M. Abdelraheem, S. Khaksar, K. Kurpiewska, J. Kalinowska-Tłuścik, S. Shaabani, A. Dömling, Two Step Macrocycle Synthesis by Classical Ugi Reaction, The Journal of organic chemistry (2018).##[49] S. Khaksar, M. Gholami, An eco-benign and highly efficient access to dihydro-1H-indeno [1, 2-b] pyridines in 2, 2, 2-trifluoroethanol, Journal of Molecular Liquids 196 (2014) 159-162.##[50] S. Khaksar, H. Radpeyma, Pentafluorophenylammonium triflate: A highly efficient catalyst for the synthesis of quinoxaline derivatives in water, Comptes Rendus Chimie 17(10) (2014) 1023-1027.##[51] S. Khaksar, S.M. Talesh, Three-component one-pot synthesis of 2, 3-dihydroquinazolin-4 (1H)-one derivatives in 2, 2, 2-trifluoroethanol, Comptes Rendus Chimie 15(9) (2012) 779-783.##[52] M.R. Nafchi, R. Ebrahimi-kahrizsangi, Synthesis of Zn-Co-TiO2 nanocomposite coatings by electrodeposition with photocatalytic and antifungal activities, Journal of Composites and Compounds 3(9) (2021) 213-217.##[53] C.K. Khatri, S.M. Potadar, G.U. Chaturbhuj, A reactant promoted solvent free synthesis of 3, 4-dihydropyrimidin-2 (1H)-thione analogues using ammonium thiocyanate, Tetrahedron Letters 58(18) (2017) 1778-1780.##[54] S. Mohammadi, Z. Mohammadi, Functionalized NiFe2O4/mesopore silica anchored to guanidine nanocomposite as a catalyst for synthesis of 4H-chromenes under ultrasonic irradiation, Journal of Composites and Compounds 3(7) (2021) 84-90.##[55] Y. Cui, C. Li, M. Bao, Deep eutectic solvents (DESs) as powerful and recyclable catalysts and solvents for the synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones/thiones, Green Processing and Synthesis 8(1) (2019) 568-576.##[56] N.S. Pawar, P.N. Patil, R.N. Pachpande, An Efficient Synthesis and Antibacterial Activity of Some Novel 3, 4–Dihydropyrimidin-2-(1H)-Ones, Chemistry Proceedings 8(1) (2021) 37.##[57] A. Mobinikhaledi, A. Yazdanipour, M. Ghashang, A green one-pot Biginelli synthesis of 3, 4-dihydropyrimidin-2-(1H)-ones catalyzed by novel Aurivillius nanostructures under solvent-free conditions, Reaction Kinetics, Mechanisms and Catalysis 119(2) (2016) 511-522.</REF>
          </REFRENCE>
        </REFRENCES>

      </ARTICLE>
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