Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

An Efficient and Sustainable Procedure for the Synthesis of Amidoalkyl Naphthols under Solvent-Free Conditions Using a Novel Graphene Oxide Based Catalyst Functionalized with 2-Aminobenzothiazole and Phosphoric Acid

Document Type : Research Article

Authors
Esmael Rostami
Maryam Sadat Ghorayshi Nejad
Ali Saberi
Seyed Mahdi Haghayeghi
Department of Basic Sciences, Faculty of Chemistry, Payam Noor University, Tehran, I.R. IRAN
Abstract
A highly efficient and sustainable procedure was described for the production of amidoalkyl naphthols using graphene oxide substituted 2-aminobenzothiazole which was activated by phosphoric acid (GO@ABTZ.H3PO4), catalyst. The synthesis was achieved using aldehydes, 2-naphthol, and acetamide (or urea) in the presence of catalyst through a one-pot three-component process without solvent. This eco-friendly catalyst managed to efficiently proceed organic synthesis processes. The proposed catalyst exhibited several advantages including cost-effectiveness, being non-metallic, providing green and environmentally-benign conditions, easy storage, facile handling, and durability. Moreover, the applied procedure has several priorities such as short reaction times, solvent-free conditions, simple work-up, and high yields. The stability and recoverability of the catalyst were also examined in five cycles which showed no considerable loss of activity.
Keywords
Graphene oxide
catalyst
phosphoric acid
2-aminobenzothiazole
amidoalkyl naphthol
multicomponent reaction
solvent-free synthesis

Subjects

[1] Zimmerman J.B., Anastas P.T., Erythropel H.C., Leitner W., Designing for a Green Chemistry Future, Science, 367(6476): 397-400 (2020).
[2] Sheldon R.A., Metrics of Green Chemistry and Sustainability: Past, Present, and Future, ACS Sustainable Chemistry & Engineering, 6(1): 32-48 (2018).
[3] صفایی م.، معینی مهر م.، سنتز چند جزئی مشتق های زانتن با استفاده از تانیک اسید و آلژینیک اسید به عنوان کاتالیست های طبیعی، شیمی و مهندسی شیمی ایران، (4)39: 73-86 (1399).
[4]  Rai V.K., Mahata S., Kashyap H., Singh M., Rai A., Bio-Reduction of Graphene Oxide: Catalytic Applications of (Reduced) GO in Organic Synthesis, Curr. Organ. Synth., 17(3): 164-191 (2020).
[5] ژیانی م.، قاسمی شرودانی ز.، کمالی س.، ساخت، بهینه سازی و ارزیابی الکتروکاتالیست آهن کبالت برروی بستر گرافن در واکنش آزادسازی هیدروژن، شیمی و مهندسی شیمی ایران، (3)38: 117-125 (1398).
[6] حسینی س. ق.، خدادادی پور ز.، سنتز نانوکامپوزیت گرافن Fe3O4/ و بررسی فعالیت کاتالیستی آن بر رفتار سوختن آمونیوم پرکلرات، نشریه شیمی و مهندسی شیمی ایران، (3)37: 71-79 (1397).
[7] قاسمی میر ش.، حسینی زوارمحله س.، حسن پور ف.، نبی پور ش.، حسگر آمپرومتری بیسفنول A بر پایه نانوورقه های گرافنی دارای نانوذره های دو فلزی پلاتین-پالادیوم، شیمی و مهندسی شیمی ایران، (2)39:  132-119 (1399).
[8] پورستار مرجانی ا.، محمودیان م.، نوزاد ا.، محمدی ه.، اصلاح گرافن اکسید به روش پلیمریزاسیون درجا و استفاده از آن به عنوان نانوذره موثر در بهبود ویژگی های مکانیکی نانوکامپوزیت پلی متیل متاکریلات، شیمی و مهندسی شیمی ایران، (4)38: 43-52 (1398).
[9] بهار س.، نوروزی آ.، سنتز و شناسایی نانوکامپوزیت مغناطیسی گرافن-L آرژینین و کاربرد آن در استخراج و پیش تغلیظ کاتیون مس، شیمی و مهندسی شیمی ایران، (2)39: 21-32 (1399).
[10] Georgakilas V., Tiwari J.N., Kemp K.C., Perman J.A., Bourlinos A.B., Kim K.S., Zboril R., Noncovalent Functionalization of Graphene and Graphene Oxide for Energy Materials, Biosensing, Catalytic, and Biomedical Applications, Chemical Reviews, 116(9): 5464-5519 (2016).
[11] Emami A., Ghafuri H., Kenari M.K., Maleki A., Investigating the Catalytic Performance of Graphene Oxide–Polyaniline–Lignosulfonate Nanocomposite in the Synthesis of Polysubstituted Pyridines via a Four‐Component Reaction, ChemistrySelect, 3(23): 6349-6357 (2018).
[12] Barrera E.G., dos Santos J.H., Designing Polyethylene Characteristics by Modification of the Support for FI Catalyst, Molecular Catalysis, 434: 1-6 (2017).
[13] Keane M.A., Catalytic Transformation of Waste Polymers to Fuel Oil, ChemSusChem: Chemistry & Sustainability Energy & Materials, 2(3): 207-214 (2009).
[14] Boudebbous K., Boulebd H., Boulcina R., Bendjeddou L., Bensouici C., Merazig H., Debache A., Synthesis, Crystal Structure, Biological Evaluation, Docking Study, and DFT Calculations of 1-Amidoalkyl-2-Naphthol Derivative, Journal of Molecular Structure, 1212: 128179 (2020).
[15] Abou-Elmagd W.S., Hashem A.I., Synthesis of 1-Amidoalkyl-2-Naphthols and Oxazine Derivatives with Study of Their Antibacterial and Antiviral Activities, Med. Chem. Res., 22(4): 2005-2013 (2013).
[16] Ghomi J.S., Zahedi S., Ghasemzadeh M.A., AgI Nanoparticles as a Remarkable Catalyst in the Synthesis of (Amidoalkyl) Naphthol and Oxazine Derivatives: An Eco-Friendly Approach, Monatshefte für Chemie-Chemical Monthly, 145(7): 1191-1199 (2014).
[17] Boudebbous K., Boulebd H., Bensouici C., Harakat D., Boulcina R., Debache A., Synthesis, Docking Study and Biological Activities Evaluation of 1‐Amidoalkyl‐2‐Naphthol Derivatives as Dual Inhibitors of Cholinesterase and α‐Glucosidase, ChemistrySelect, 5(19): 5515-5520 (2020).
[18] Rahimizadeh R., Mobinikhaledi A., Moghanian H., Kashaninejad S. S., Design and Synthesis of Some New Biologically Active Amidoalkyl Naphthols in the Presence of Sulfonic Acid Functionalized Silica-Coated Fe3O4 Nanoparticles, Res. Chem. Inter., 48(2): 607-627 (2022).
[19] Bankar S.R., Shelke S.N., Nanomagnetite-Supported Molybdenum Oxide (Nanocat-Fe-Mo): An Efficient Green Catalyst for Multicomponent Synthesis of Amidoalkyl Naphthols, Research on Chemical Intermediates, 44(5): 3507-3521 (2018).
[20] Kooti M., Karimi M., Nasiri E., A Novel Copper Complex Supported on Magnetic Reduced Graphene Oxide: An Efficient and Green Nanocatalyst for the Synthesis of 1-Amidoalkyl-2-Naphthol Derivatives, Journal of Nanoparticle Research, 20(2): 1-14 (2018).
[21] Li F., Zhang J., Wang L., Liu W., Yousif Q.A., Solvent-Free Synthesis of 1-Amidoalkyl-2-Naphthol and 3-Amino-1-Phenyl-1H Benzo [f] Chromene-2-Carbonitrile Derivatives by Fe3O4@Enamine-B (OSO3H)2 as an Efficient and Novel Heterogeneous Magnetic Nanostructure Catalyst, Polish Journal of Chemical Technology, 22(2): 9-19 (2020).
[22] Hoseini Z., Davoodnia A., Khojastehnezhad A., Pordel M., Phosphotungstic Acid Supported on Functionalized Graphene Oxide Nanosheets (GO-SiC3-NH3-H2PW): Preparation, Characterization, and First Catalytic Application in the Synthesis of Amidoalkyl Naphthols, Eurasian Chemical Communications, 2(3): 398-409 (2020).
[23] Ahmadi M., Moradi L., Sadeghzadeh M., Solvent-Free Synthesis of Amidoalkyl Naphthols in the Presence of MWCNTs@SiO2/SO3H as Effective Solid Acid Catalyst, Monatshefte für Chemie-Chemical Monthly, 150(6): 1111-1119 (2019).
[24] Abera D., Tesso H., Belay A., Synthesis of Some Amidoalkyl Naphthol and Benzoxanthene Derivatives by Zinc Oxide Nanoparticles Catalyst Under Solvent-Free Condition and Evaluation of Their Antimicrobial and Antioxidant Activities, Synthesis, 11(7): 15-25 (2019).
[25] Govindhan C., Nagarajan P.S., 2,6‐Pyridinedicarboxylic Acid (PDCA) Catalyzed Improved Synthetic Approach for 1‐Amidoalkyl Naphthols, Dihydropyrimidin‐2 (1H)‐ones and Bis‐Indoles, ChemistrySelect, 6(33): 8716-8726 (2021).
[26] Bahrami S., Jamehbozorgi S., Moradi S., Ebrahimi S., Synthesis of 1‐Amidoalkyl‐2‐Naphthol Derivatives Using a Magnetic Nano‐Fe3O4@SiO2@Hexamethylenetetramine‐Supported Ionic liquid as a Catalyst Under Solvent‐Free Conditions, J. Chin. Chem. Soci., 67(4): 603-609 (2020).
[27] Madankumar N., Pitchumani K., β‐Cyclodextrin‐Monosulphonic Acid Catalyzed Efficient Synthesis of 1‐Amidoalkyl‐2‐Naphthols, ChemistrySelect, 2(33): 10798-10803 (2017).
[28] Dipake S.S., Gadekar S.P., Thombre P.B., Lande M.K., Rajbhoj A.S., Gaikwad S.T., ZS-1 Zeolite as a Highly Efficient and Reusable Catalyst for Facile Synthesis of 1-Amidoalkyl-2-Naphthols Under Solvent-Free Conditions, Catalysis Letters, 151: 1-16 (2021).
[29] Hummers W.S., Offeman R.E., Graphene Oxide, Journal of the American Chemical Society, 80: 1339 (1958).
[30] Santamaría-Juárez G., Gómez-Barojas E., Quiroga-González E., Sánchez-Mora E., Quintana-Ruiz M., Santamaría-Juárez J.D., Safer Modified Hummers’ Method for the Synthesis of Graphene Oxide with High Quality and High Yield, Mater. Res. Express, 6(12): 125631 (2020).
[31] Priyadarshini E., Pradhan N., Sukla L.B., Panda P.K., Controlled Synthesis of Gold Nanoparticles Using Aspergillus Terreus IF0 and Its Antibacterial Potential Against Gram Negative Pathogenic Bacteria, Journal of Nanotechnology, 2014: 1-9 (2014).
[32] Errahali M., Gatti G., Tei L., Canti L., Fraccarollo A., Cossi M., Marchese L., Understanding Methane Adsorption in Porous Aromatic Frameworks: An FTIR, Raman, and Theoretical Combined Study, The Journal of Physical Chemistry C, 118(19): 10053-10060 (2014).
[33] Guan L., Xu H., Huang D., The Investigation on States of Water in Different Hydrophilic Polymers by DSC and FTIR, Journal of Polymer Research, 18(4): 681-689 (2011).
[34] Kvarnström C., Petr A., Damlin P., Lindfors T., Ivaska A., Dunsch L., Raman and FTIR Spectroscopic Characterization of Electrochemically Synthesized Poly (Triphenylamine), PTPA, Journal of Solid State Electrochemistry, 6(8): 505-512 (2002).
[35] Yao S.F., Chen X.T., Ye H.M., Investigation of Structure and Crystallization Behavior of Poly (Butylene Succinate) by Fourier Transform Infrared Spectroscopy, The Journal of Physical Chemistry B, 121(40): 9476-9485 (2017).
[36] Dunkhunthod B., Thumanu K., Eumkeb G., Application of FTIR Microspectroscopy for Monitoring and Miscrimination of the Anti-Adipogenesis Activity of Baicalein in 3T3-L1 Adipocytes, Vibrational Spectroscopy, 89: 92-101 (2017).
[37] Jin S., Qian L., Qiu Y., Chen Y., Xin F., High-Efficiency Flame Retardant Behavior of Bi-DOPO Compound with Hydroxyl Group on Epoxy Resin, Polymer Degradation and Stability, 166: 344-352 (2019).
[38] Das P.K., Mohapatra R.K., Patjoshi S.B., El-ajaily M.M., Dash D.C., Synthesis, Spectral Characterization and Antimicrobial Studies of Transition Metal Complexes of Benzothiazole Based Schiff Bases, Asian Journal of Chemistry, 30(12): 2608-2614 (2018).
[39] Mary Y.S., Varghese H.T., Panicker C.Y., Ertan T., Yildiz I., Temiz-Arpaci O., Vibrational Spectroscopic Studies and Ab initio Calculations of 5-Nitro-2-(p-Fluorophenyl) Benzoxazole, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71(2): 566-571 (2008).
[40] Tawiah B., Yu B., Yuen R.K., Hu Y., Wei R., Xin J.H., Fei B., Highly Efficient Flame Retardant and Smoke Suppression Mechanism of Boron Modified Graphene Oxide/Poly (Lactic acid) Nanocomposites, Carbon, 150: 8-20 (2019).
[41] Baran N.Y., Generation and Characterization of Palladium Nanocatalyst Anchored on a Novel Polyazomethine Support: Application in Highly Efficient and Quick Catalytic Reduction of Environmental Contaminant Nitroarenes, Journal of Molecular Structure, 1220: 128697 (2020).
[42] Hirashima Y., Sato H., Suzuki A., ATR-FTIR Spectroscopic Study on Hydrogen Bonding of Poly (N-Isopropylacrylamide-Co-Sodium Acrylate) Gel, Macromolecules, 38(22): 9280-9286 (2005).
[43] Li R.W., Ventura L., Gruber J., Kawano Y., Carvalho L.R., A Selective Conductive Polymer-Based Sensor for Volatile Halogenated Organic Compounds (VHOC), Sensors and Actuators B: Chemical, 131(2): 646-651 (2008).
[44] Kojio K., Nakashima S., Furukawa M., Microphase-Separated Structure and Mechanical Properties of Norbornane Diisocyanate-Based Polyurethanes, Polymer, 48(4): 997-1004 (2007).
[45] Wang F., Liao Q., Chen K., Pan S., Lu M., The Crystallization and FTIR Spectra of ZrO2-Doped 36Fe2O3–10B2O3–54P2O5 Glasses and Crystalline Compounds, Journal of Alloys and Compounds, 611: 278-283 (2014).
[46] Hakiri R., Ameur I., Abid S., Derbel N., Synthesis, X-ray Structural, Hirshfeld Surface Analysis, FTIR, MEP and NBO Analysis Using DFT Study of a 4-Chlorobenzylammonium Nitrate (C7ClH9N)+(NO3)–, Journal of Molecular Structure, 1164: 486-492 (2018).
[47] Samouhos M., Tsakiridis P., One-Step Synthesis of Amino-Functionalized Carbon Nanoparticles and Their Dispersion in Graphene Oxide. A Physicochemical Study, Mater. Lett., 254: 133-136 (2019).
[48] Chen M., Chen Y., Zhou X., Lu B., He M., Sun S., Ling X., Improving Water Resistance of Soy-Protein Wood Adhesive by Using Hydrophilic Additives, BioResources, 10(1): 41-54 (2015).
[49] Khiabani A.B., Rahimi S., Yarmand B., Mozafari M., Electrophoretic Deposition of Graphene Oxide on Plasma Electrolytic Oxidized-Magnesium Implants for Bone Tissue Engineering Applications, Materials Today: Proceedings, 5(7): 15603-15612 (2018).
[50] Vimala P.P., Mathew L., Biodegradation of Polyethylene Using Bacillus Subtilis, Procedia Technology, 24: 232-239 (2016).
[51] Baig N., Shetty S., Moustafa M.S., Al-Mousawi S., Alameddine B., Selective Removal of Toxic Organic Dyes Using Trӧger Base-Containing Sulfone Copolymers Made from a Metal-Free Thiol-Yne Click Reaction Followed by Oxidation, RSC Advances, 11(34): 21170-21178 (2021).
[52] Asensio J.A., Borrós S., Gómez‐Romero P., Proton‐Conducting Polymers based on Benzimidazoles and Sulfonated Benzimidazoles, J. Poly. Sci. Part A: Poly. Chem., 40(21): 3703-3710 (2002).
[53] Qin Z.H., Chen H., Yan Y.J., Li C.S., Rong L.M., Yang X.Q., FTIR Quantitative Analysis Upon Solubility of Carbon Disulfide/N-Methyl-2-pyrrolidinone Mixed Solvent to Coal Petrographic Constituents, Fuel Processing Technology, 133: 14-19 (2015).
[54] Zhang Q., He Y., Chen X., Hu D., Li L., Yin T., Ji L., Structure and Photocatalytic Properties of TiO2-Graphene Oxide Intercalated Composite, Chinese Science Bulletin, 56(3): 331-339 (2011).
[55] Cong H.P., He J.J., Lu Y., Yu S.H., Water‐Soluble Magnetic‐Functionalized Reduced Graphene Oxide Sheets: In Situ Synthesis and Magnetic Resonance Imaging Applications, Small, 6(2): 169-173 (2010).
[56] Zhang F., Jin J., Zhong X., Li S., Niu J., Li R., Ma J., Pd Immobilized on Amine-Functionalized Magnetite Nanoparticles: A Novel and Highly Active Catalyst for Hydrogenation and Heck Reactions, Green Chemistry, 13(5): 1238-1243 (2011).
[57] Xiao R., Yang W., Cong X., Dong K., Xu J., Wang D., Yang X., Thermogravimetric Analysis and Reaction Kinetics of Lignocellulosic Biomass Pyrolysis, Energy, 201: 117537 (2020).
[58] Jaikumar A., Kandlikar S.G., Gupta A., Pool Boiling Enhancement through Graphene and Graphene Oxide Coatings, Heat Transfer Engineering, 38(14-15): 1274-1284 (2017).
[59] Zhang Q., Gao Y.H., Qin S.L., Wei H.X., Facile One-Pot Synthesis of Amidoalkyl Naphthols and Benzopyrans Using Magnetic Nanoparticle-Supported Acidic Ionic Liquid as a Highly Efficient and Reusable Catalyst, Catalysts, 7(11): 351 (2017).
[60] Torabi M., Yarie M., Zolfigol M.A., Azizian S., Magnetic Phosphonium Ionic Liquid: Application as a Novel Dual Role Acidic Catalyst for Synthesis of 2′-Aminobenzothiazolomethylnaphthols and Amidoalkyl Naphthols, Research on Chemical Intermediates, 46(1): 891-907 (2020).
[61] Ghorbani F., Kiyani H., Pourmousavi S.A., Ajloo D., Solvent-Free Synthesis of 1-Amidoalkyl-2-Naphthols Using Magnetic Nanoparticle-Supported 2-(((4-(1-Iminoethyl) Phenyl) Imino) Methyl) Phenol Cu (II) or Zn (II) Schiff Base Complexes, Res. Chem. Inter., 46(6): 3145-3164 (2020).
[62] Rostami E., Hamidi Zare S., Double Brønsted Acidic Media Immobilized on Carbonized Sugarcane Bagasse (CSCB) as a New and Efficient Solid Acid Catalyst for the Synthesis of Coumarins, Dicoumarols and Xanthenes, ChemistrySelect, 4(45): 13295-13303 (2019).
[63] Sapkal S.B., Shelke K.F., Madje B.R., Shingate B.B., Shingare M.S., 1-Butyl-3-Methyl Imidazolium Hydrogen Sulphate Promoted One-Pot Three-Component Synthesis of Amidoalkyl Naphthols, Bulletin of the Korean Chemical Society, 30(12): 2887-2889 (2009).
[64] Dorehgiraee A., Khabazzadeh H., Saidi K., Heteropoly Acid Catalyzed Synthesis of 1-Amidoalkyl-2-Naphthols in the Presence of Molten Tetraethylammonium Chloride, Arkivoc, 7: 303-310 (2009).
[65] Safari J., Zarnegar Z., Ultrasound Mediation for One-Pot Multi-Component Synthesis of Amidoalkyl Naphthols Using New Magnetic Nanoparticles Modified by Ionic Liquids, Ultrasonics Sonochemistry, 21(3): 1132-1139 (2014).
[66] Supal A.R., Gokavi G.S., An Environmentally Benign Three Component One-Pot Synthesis of Amidoalkyl Naphthols Using H4SiW12O40 as a Recyclable Catalyst, Journal of Chemical Sciences, 122(2): 189-192 (2010).
[67] Khabazzadeh H., Saidi K., Seyedi N., Cu-Exchanged Heteropoly Acids as Efficient and Reusable Catalysts for Preparation of 1-Amidoalkyl-2-Naphthols, J. Chem. Sci., 121(4): 429-433 (2009).
[68] Narayanan D.P., Cherikallinmel S.K., Sankaran S., Narayanan B.N., Functionalized Carbon Dot Adorned Coconut Shell Char Derived Green Catalysts for the Rapid Synthesis of Amidoalkyl Naphthols, Journal of Colloid and Interface Science, 520: 70-80 (2018).
[69] Srihari G., Nagaraju M., Murthy M.M., Solvent‐Free One‐Pot Synthesis of Amidoalkyl Naphthols Catalyzed by Silica Sulfuric Acid, Helvetica Chimica Acta, 90(8): 1497-1504 (2007).
[70] Rekunge D.S., Bendale H.S., Chaturbhuj G.U., Activated Fuller’s Earth: an Efficient, Inexpensive, Environmentally Benign, and Reusable Catalyst for Rapid Solvent-Free Synthesis of 1-(Amido/Amino) Alkyl-2-Naphthols, Mona. für Chem.-Chem. Mon., 149(11): 1991-1997 (2018).
[71] Pourmousavi S.A., Moghimi P., Ghorbani F., Zamani M., Sulfonated Polynaphthalene as an Effective and Reusable Catalyst for the One-Pot Preparation of Amidoalkyl Naphthols: DFT and Spectroscopic Studies, Journal of Molecular Structure, 1144: 87-102 (2017).
[72] Hakimi F., Silver nanoparticles: an Efficient and Versatile Reagent for the Synthesis of 1-Amidoalkyl-2-Naphthols, Inorganic and Nano-Metal Chemistry, 47(7): 994-998 (2017).