115
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis of 1,2,4-Triazol-3-Selones via a Three-Component Condensation Between Furan-2-Carbohydrazide, Potassium Selenocyanate and Aroyl Chlorides

, ORCID Icon, ORCID Icon & ORCID Icon
Pages 488-494 | Received 18 Aug 2022, Accepted 28 Jan 2023, Published online: 13 Mar 2023

References

  • L. Weber, “The Application of Multi-Component Reactions in Drug Discovery,” Current Medicinal Chemistry 9, no. 23 (2002): 2085–93. doi:10.2174/0929867023368719
  • S. Rostamnia, “In Situ Generation and Protonation of the Isocyanide/Acetylene Adduct: A Powerful Catalyst-Free Strategy for Multicomponent Synthesis of Ketenimines, Aza-Dienes, and Heterocycles,” RSC Advances 5, no. 117 (2015): 97044–65. doi:10.1039/C5RA20455K
  • E. Doustkhah, A. Baghban, M. H. N. Assadi, R. Luque, and S. Rostamnia, “Mesoporous SBA-15/PIDA as a Dendrimer Zwitterionic Amino Acid-Type Organocatalyst for Three-Component Indazolophtalazine Synthesis,” Catalysis Letters 149, no. 2 (2019): 591–600. doi:10.1007/s10562-018-2643-6
  • E. Doustkhah, S. Rostamnia, and A. Hassankhani, “The Raise of SBA-SO3H Catalytic Activity by Inducing Ultrasound Irradiation in the Multicomponent Syntheses,” Journal of Porous Materials 23, no. 2 (2016): 549–56. doi:10.1007/s10934-015-0108-5
  • S. Gaikwad, M. Venkata, and B. Unnamatla, “Simple, Highly Efficient Synthesis of 2-Amino-4-Phenyl-4,5,6,7-Tetrahydropyrano[3,2-c]Carbazole-3-Carbonitrile Derivatives Using Silica Supported Dodeca-Tungstophosphoric Acid DTP/SiO2,” Journal of Applied Organometallic Chemistry 2 (2022): 24–30.
  • A. R. Salih, and Z. A. K. Al-Messri, “Synthesis of Pyranopyrazole and Pyranopyrimidine Derivatives Using Magnesium Oxide Nanoparticles and Evaluation as Corrosion Inhibitors for Lubricants,” Eurasian Chemical Communications 3 (2021): 533–41.
  • N. Pahade, D. Wagare, D. W. Shinde, and D. Lingampalle, “Ionic Liquid Catalyzed One-Pot Synthesis of 5-(4-Substituted-Phenyl)-1,3,4-Thiadiazole-2-Amines,” Polycyclic Aromatic Compounds. doi:10.1080/10406638.2022.2150239.
  • S. Udgire, M. Gaikwad, and P. Patil, “Bi(OTf)3 as a Highly Potent Catalyst for the Synthesis of Mannich Bases under Milder Conditions,” Journal of Applied Organometallic Chemistry 2 (2022): 31–8.
  • B. Maleki, H. Natheghi, R. Tayebee, and H. Alinezhad, “Synthesis and Characterization of Nanorod Magnetic Co–Fe Mixed Oxides and Its Catalytic Behavior towards One-Pot Synthesis of Polysubstituted Pyridine Derivatives,” Polycyclic Aromatic Compounds 42 (2022): 1–11.
  • B. Maleki, H. Atharifar, O. Reiser, and R. Sabbaghzadeh, “Glutathione-Coated Magnetic Nanoparticles for One-Pot Synthesis of 1,4-Dihydropyridine Derivatives,” Polycyclic Aromatic Compounds 41, no. 4 (2021): 721–34. doi:10.1080/10406638.2019.1614639
  • B. Maleki, and S. Sheikh, “Nano Polypropylenimine Dendrimer (DAB-PPI-G1): As a Novel Nano Basic-Polymer Catalyst for One-Pot Synthesis of 2-Amino-2-Chromene Derivatives,” RSC Advances 5, no. 54 (2015): 42997–3005. doi:10.1039/C5RA04458H
  • H. Alinezhad, M. Tajbakhsh, B. Maleki, and F. Pourshaban Oushibi, “Acidic Ionic Liquid [H-NP]HSO4 Promoted One-Pot Synthesis of Dihydro-1H-Indeno[1,2-b]Pyridines and Polysubstituted Imidazoles,” Polycyclic Aromatic Compounds 40, no. 5 (2020): 1485–500. doi:10.1080/10406638.2018.1557707
  • H. Atharifar, A. Keivanloo, and B. Maleki, “Greener Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-Ones in a Deep Eutectic Solvent,” Organic Preparations and Procedures International 52, no. 6 (2020): 517–23. doi:10.1080/00304948.2020.1799672
  • B. Maleki, and S. Sheikh, “One-Pot Synthesis of 2-Amino-2-Chromene and 2-Amino-3-Cyano-4H-Pyran Derivatives Promoted by Potassium Fluoride,” Organic Preparations and Procedures International 47, no. 5 (2015): 368–78. doi:10.1080/00304948.2015.1066647
  • F. Laffafchi, M. Tajbakhsh, Y. Sarrafi, B. Maleki, and M. Ghani, “Cu-Modified Magnetic Creatine as an Efficient Catalyst for Regioselective Preparation of 1,2,3-Triazoles Derivatives,” Polycyclic Aromatic Compounds. doi:10.1080/10406638.2022.2070224
  • J. Ghanaat, M. A. Khalilzadeh, and D. Zareyee, “Molecular Docking Studies, Biological Evaluation and Synthesis of Novel 3-Mercapto-1,2,4-Triazole Derivates,” Molecular Diversity 25, no. 1 (2021): 223–32. doi:10.1007/s11030-020-10050-0
  • S. K. De, J. L. Stebbins, L.-H. Chen, M. Riel-Mehan, T. Machleidt, R. Dahl, H. Yuan, A. Emdadi, E. Barile, V. Chen, et al, “Design, Synthesis, and Structure Activity Relationship of Substrate Competitive, Selective and in Vivo Active Triazole and Thiadiazole Inhibitors of the c-Jun N-Terminal Kinase,” Journal of Medicinal Chemistry 52, no. 7 (2009): 1943–52. doi:10.1021/jm801503n
  • K. M. Krishna, B. Inturi, G. V. Pujar, M. N. Purohit, and G. S. Vijaykumar, “Design, Synthesis and 3D-QSAR Studies of New Diphenylamine Containing 1,2,4-Triazoles as Potential Antitubercular Agents,” European Journal of Medicinal Chemistry 84 (2014): 516–29. doi:10.1016/j.ejmech.2014.07.051
  • B. N. Goswami, J. C. S. Kataky, and J. N. Baruah, “Synthesis and Antibacterial Activity of 1-(2,4-Dichlorobenzoyl)-4-Substituted Thiosemicarbazides,1,2,4-Triazoles and Their Methyl Derivatives,” Journal of Heterocyclic Chemistry 21, no. 4 (1984): 1225–9. doi:10.1002/jhet.5570210460
  • S. Tehranchian, T. Akbarzadeh, M. Fazeli, M. Reza, H. Jamalifar, and A. Shafiee, “Synthesis and Antibacterial Activity of 1-[1,2,4-Triazol-3-yl] and 1-[1,3,4-Thiadiazol-2-yl]-3-Methylthio-6,7-Dihydrobenzo[c]Thiophen-4(5H)Ones,” Bioorganic & Medicinal Chemistry Letters 15, no. 4 (2005): 1023–5. doi:10.1016/j.bmcl.2004.12.039
  • A. K. Dimri, and S. S. Parmar, “Synthesis of 3-Aryl-4-Oxothiazolin-2-yl(4-Ethoxy-3-Methoxy)Phenyl Hydrazones as Possible Anticonvulsants,” Journal of Heterocyclic Chemistry 15, no. 2 (1978): 335–6. doi:10.1002/jhet.5570150235
  • S. Radl, “Preparation of Some Pyrazole Derivatives by Extrusion of Elemental Sulfur from 1,3,4-Thiadiazines,” Collection of Czechoslovak Chemical Communications 57, no. 3 (1992): 656–9. doi:10.1135/cccc19920656
  • M. Nutiu, V. Bercean, and M. Birau, “Synthesis of Some 4-Aryl-Thiosemicarbazides,” Annals of West University of Timisoara 5 (1996): 7–10.
  • S. M. Golovlyova, Y. A. Moskvichev, E. M. Alov, D. B. Kobylinsky, and V. V. Ermolaeva, “Synthesis of Novel Five-Membered Nitrogencontaining Heterocyclic Compounds from Derivatives of Arylsulfonyl and Arylthioacetic and Propionic Acids,” Chemistry of Heterocyclic Compounds 37, no. 9 (2001): 1102–6. doi:10.1023/A:1013275515682
  • I. Ledeţi, V. Bercean, A. Alexa, C. Şoica, L.-M. Şuta, C. Dehelean, C. Trandafirescu, D. Muntean, M. Licker, and A. Fuliaş, “Preparation and Antibacterial Properties of Substituted 1,2,4-Triazoles,” Journal of Chemistry 2015 (2015): 1–5. doi:10.1155/2015/879343
  • P. J. Garratt, “Apractical Methylation Procedure for (1H)-1,2,4-Trazole,” in Comprehensive Heterocyclic Chemistry, edited by A. R. Katritzky, C. W. Rees, and E. F. V. Sriven, vol. 4, 2nd ed. (Oxford: Elsevier, 1996), 127–63.
  • K. Turnbull, “Five-Membered Ring Systems with More than One Nitrogen Atom,” in Progress in Heterocyclic Chemistry, edited by G. W. Gribble and J. A. Joule, vol. 10 (Oxford: Elsevier, 1998), 153–71.
  • M. Balasubramanian, J. G. Keay, E. F. V. Scriven, and N. Shobana, “Approches to the Synthesis of 1-Substituted 1,2,4-Triazoles,” Heterocycles 37, no. 3 (1994): 1951–75. doi:10.3987/REV-93-SR11
  • J. Angulo, M. Serrano, and L. Henning, “Synthesis and Characterization of 1,5-Diphenyl-1,2,4-Triazole-Thion,” Revista de la Sociedad Química Del Perú 69 (2003): 131–42.
  • I. Yavari, F. Shirgahi-Talari, Z. Hossaini, M. Sabbaghan, and S. Seyfi, “Synthesis of Functionalized 1,2,4-Triazole-3-Thiones from Ammonium Isothiocyanate, Acid Chlorides, and Arylhydrazines,” Molecular Diversity 14, no. 4 (2010): 763–6. doi:10.1007/s11030-009-9218-9
  • T. Wirth, Organoselenium Chemistry: Synthesis and Reactions (Weinheim, Germany: Wiley-VCH, 2012), 1–51.
  • M. O. Sydnes, and M. Isobe, “Exclusive Formation of Azo-Compounds upon Hydrogenolysis of Nitrobenzeneseleninic Acid Derivatives over Pd/C,” Monatshefte Für Chemie – Chemical Monthly 146, no. 2 (2015): 351–6. doi:10.1007/s00706-014-1373-8
  • A. C. Razus, L. Birzan, A. Hanganu, M. Cristea, E.-M. Ungureanu, M.-L. Soare, and G.-O. Buica, “1-Phenylselanylazulenes: synthesis and Selenium Atom Oxidation,” Monatshefte Für Chemie – Chemical Monthly 145, no. 12 (2014): 1999–2009. doi:10.1007/s00706-014-1297-3
  • M. D. Rvovic, V. M. Divac, N. Z. Jankovic, and Z. M. Bugarcic, “Cyclization of Some Terpenic Alcohols by Phenylselenoetherification Reaction,” Monatshefte Für Chemie – Chemical Monthly 144, no. 8 (2013): 1227–31. doi:10.1007/s00706-013-1006-7
  • N. Filipovic, N. Polovic, B. Raskovic, S. Misirlic-Dencic, M. Dulovic, M. Savic, M. Niksic, D. Mitic, K. Andelkovic, and T. Todorovic, “Biological Activity of Two Isomeric N-Heteroaromatic Selenosemicarbazones and Their Metal Complexes,” Monatshefte Für Chemie – Chemical Monthly 145 (2014): 1089–99.
  • M. H. Mosslemin, M. Anary-Abbasinejad, A. Hassanabadi, and M. A. Bagheri, “Three-Component Reaction between Triphenylphosphine, Dialkyl Acetylene Dicarboxylate and 4-Amino-5-Alkyl-2,4-Dihydro-1,2,4-Triazole-3-Thiones: An Efficient One-Pot Synthesis of Stable Phosphorus Ylides,” Journal of Sulfur Chemistry 31, no. 2 (2010): 135–9. doi:10.1080/17415991003682617
  • A. Hassanabadi, M. H. Mosslemin, and S. E. Tadayonfar, “Three-Component Reaction between 4-Hydroxycoumarin, Ammonium Thiocyanate and Acid Chlorides in the Presence of N-Methylimidazole under Solvent-Free Conditions,” Journal of Chemical Research 35, no. 1 (2011): 29–31. doi:10.3184/174751911X1296493007681
  • I. Yavari, and S. Mosaferi, “A One-Pot Synthesis of 2H-Pyrido[1,2-a][1,3,5]Triazine-2-Selenones from Acyl Isoselenocyanates and Pyridin-2-Amine,” Monatshefte Für Chemie – Chemical Monthly 148, no. 5 (2017): 963–6. doi:10.1007/s00706-016-1834-3

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.