Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

A Modified Green Method for the Preparation of MgO Nanopowders as Efficient Catalysts for the Synthesis of Pyrano[4,3-d]Thiazolo [3,2-a]Pyrimidine Derivatives

Document Type : Research Article

Authors
Mehdi Khalaj 1
Ali Mahmoudi 2
1 Department of Chemistry, Islamic Azad University, Buinzahra Branch, Buinzahra, I.R. IRAN
2 Department of Chemistry, Islamic Azad University, Tehran North Branch, Tehran, I.R. IRAN
Abstract
In this research, three simple methods including thermal, ultrasonic irradiation, and high-speed milling method (HSBM) techniques for the preparation of pyrano[4,3-d]thiazolo[3,2-a]pyrimidine derivatives in the presence of MgO nanopowders under solvent-free conditions has been reported. MgO nanopowders were prepared in an aqueous solution containing freshly squeezed orange juice with pulp and characterized by XRD, FE-SEM, EDS, and FT-IR techniques.
Keywords
MgO Nanopowders, Pyrimidines, HSBM technique, Pyran
Thiazolo[3,2-a]pyrimidine

Subjects

[1] Marset X., Khoshnood A., Sotorríos L., Gómez-Bengoa E., Alonso D.A., Ramón D.J., Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross‐Coupling Reactions, Chem. Cat. Chem., 9: 1269-1275 (2017).
[2] Sandfort F., O'Neill M.J., Cornella J., Wimmer L., Baran P.S., Alkyl−(Hetero)Aryl Bond Formation via Decarboxylative Cross-Coupling: A Systematic Analysis, Angew. Chem. Int. Ed., 56: 3319-3323 (2017).
[3] Brambilla M., Tredwell M., Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling of Secondary α-(Trifluoromethyl)Benzyl Tosylates, Angew. Chem. Int. Ed., 56: 11981-11985 (2017).
[4] Serra J., Parella T., Ribas X., Au(III)-aryl Intermediates in Oxidant-Free C–N and C–O Cross-Coupling Catalysis, Chem. Sci., 8: 946-952 (2017).
[5] Myers A.G., Tanaka D., Mannion M.R., Development of a Decarboxylative Palladation Reaction and Its Use in a Heck-type Olefination of Arene Carboxylates, J. Am. Chem. Soc., 124: 11250-11251 (2002).
[6] Hu G., Gao Y., Zhao Y.,Copper-Catalyzed Decarboxylative C–P Cross-Coupling of Alkynyl Acids with H-Phosphine Oxides: A Facile and Selective Synthesis of (E)-1-Alkenylphosphine Oxides, Org. Lett., 16: 4464-4467 (2014).
[7] Kan J., Huang S., Lin J., Zhang M., Su W., Silver‐Catalyzed Arylation of (Hetero)Arenes by Oxidative Decarboxylation of Aromatic Carboxylic Acids, Angew. Chem. Int. Ed., 54: 2199-2203 (2015).
[8] Sun F., Gu Z., Decarboxylative Alkynyl Termination of Palladium-Catalyzed Catellani Reaction: A Facile Synthesis of α-Alkynyl Anilines via Ortho C–H Amination and Alkynylation, Org. Lett., 17: 2222-2225 (2015).
[9] Gooßen L.J., Lange P.P., Rodríguez N., Linder C., Low‐Temperature Ag/Pd‐Catalyzed Decarboxylative Cross‐Coupling of Aryl Triflates with Aromatic Carboxylate Salts, Chem. Eur. J., 16: 3906-3909 (2010).
[10] Gooßen L.J., Deng G., Levy L.M., Synthesis of Biaryls Via Catalytic Decarboxylative Coupling, Science., 313: 662-664 (2006).
[11] Rudolphi F., Song B., Gooßen L.J., Decarboxylative Coupling of α‐Keto Acids with Ortho‐Phenylenediamines Promoted by an Electrochemical Method in Aqueous Media, Adv. Synth. Catal., 358(12): 1975-1981 (2011).
[12] Heck R.F., Mechanism of Arylation and Carbomethoxylation of Olefins with Organopalladium Compounds, J. Am. Chem. Soc., 91: 6707-6714 (1969).
[13] Traficante C.I., Fagundez C., Serra G.L., Mata E.G., Delpiccolo C.M.L.,Chemoselective and Sequential Palladium-Catalyzed Couplings for the Generation of Stilbene Libraries via Immobilized Substrates, ACS Comb. Sci., 18: 225-229 (2016).
[14] Kong W., Che C., Wu J., Ma L., Zhu G., Palladium-Catalyzed Hydroarylation, Hydroalkenylation, and Hydrobenzylation of Ynol Ethers with Organohalides: A Regio- and Stereoselective Entry to α,β- and β,β-Disubstituted Alkenyl Ethers, J. Org. Chem., 79: 5799-5805 (2014).
[15] Gordillo A., Ortuño M.A., López-Mardomingo C., Lledós A., Ujaque G., de Jesús E., Mechanistic Studies on the Pd-Catalyzed Vinylation of Aryl Halides with Vinylalkoxysilanes in Water: The Effect of the Solvent and NaOH Promoter, J. Am. Chem. Soc., 135: 13749-13763 (2013).
[16] Huang L., Biafora A., Zhang G., Bragoni V., Gooßen L.J., Regioselective C−H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups, Angew. Chem. Int. Ed., 55: 6933-6937 (2016).
[17] Manikandan R., Jeganmohan M., Recent Advances in the Ruthenium-Catalyzed Hydroarylation of Alkynes with Aromatics: Synthesis of Trisubstituted Alkenes, Org. Biomol. Chem., 13: 10420-10436 (2015).
[18] Khalaj M., Ghazanfarpour-Darjani M., Talei Bavil Olyai M.R., Faraji Shamami S., Palladium Nanoparticles as Reusable Catalyst for the Synthesis of N-Aryl Sulfonamides Under Mild Reaction Conditions, Journal of Sulfur Chemistry., 37: 211-222 (2016).
[19] Khalaj M., Ghazanfarpour-Darjani M., Cross-Coupling Reaction of Aryl Diazonium Salts with Azodicarboxylate Using FeCl2, RSC Adv., 5: 80698-80701 (2015).