Three-component reaction between ethyl carbazate, potassium selenocyanate and aroyl chlorides: Synthesis of 1,2,4-triazole-3-selones

References

• Ghanaat, J.; Khalilzadeh, M. A.; Zareyee, D. Molecular Docking Studies, Biological Evaluation and Synthesis of Novel 3-mercapto-1,2,4-triazole derivatives. Mol. Divers. 2021, 25, 223–232. DOI: 10.1007/s11030-020-10050-0.
   PubMed Web of Science ®Google Scholar
• De, S.; Stebbins, J.; Chen, L.-H.; Riel-Mehan, M.; Machleidt, T.; Dahl, R.; Yuan, H.; Emdadi, A.; Barile, E.; Chen, V.; 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. J. Med. Chem. 2009, 52, 1943–1952. DOI: 10.1021/jm801503n.
   PubMed Web of Science ®Google Scholar
• Krishna, K. M.; Inturi, B.; Pujar, G. V.; Purohit, M. N.; Vijaykumar, G. S. Design, Synthesis and 3D-QSAR Studies of New Diphenylamine Containing 1,2,4-Triazoles as Potential Antitubercular Agents. Eur. J. Med. Chem. 2014, 84, 516–529. DOI: 10.1016/j.ejmech.2014.07.051.
   PubMed Web of Science ®Google Scholar
• Goswami, B. N.; Kataky, J. C. S.; Baruah, J. N. Synthesis and Antibacterial Activity of 1-(2,4-Dichlorobenzoyl)-4-Substituted Thiosemicarbazides,1,2,4-Triazoles and Their Methyl Derivatives. J. Heterocycl. Chem. 1984, 21, 1225–1229. DOI: 10.1002/jhet.5570210460.
   Web of Science ®Google Scholar
• Tehranchian, S.; Akbarzadeh, T.; Fazeli, M.; Reza, M.; Jamalifar, H.; Shafiee, A. 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. Bioorg. Med. Chem. Lett. 2005, 15, 1023–1025. DOI: 10.1016/j.bmcl.2004.12.039.
   PubMed Web of Science ®Google Scholar
• Dimri, A. K.; Parmar, S. S. Synthesis of 3-Aryl-4-Oxothiazolin-2-yl(4-Ethoxy-3-Methoxy)Phenyl Hydrazones as Possible Anticonvulsants. J. Heterocycl. Chem. 1978, 15, 335–336. DOI: 10.1002/jhet.5570150235.
   Web of Science ®Google Scholar
• Radl, S. Preparation of Some Pyrazole Derivatives by Extrusion of Elemental Sulfur from 1,3,4-Thiadiazines. Collect. Czech Chem.Commun. 1992, 57, 656–659. DOI: 10.1135/cccc19920656.
   Google Scholar
• Nutiu, M.; Bercean, V.; Birau, M. Synthesis of Some 4-Aryl-Thiosemicarbazides. Ann. West Univ. Timis 1996, 5, 7–10.
   Google Scholar
• Golovlyova, S. M.; Moskvichev, Y. A.; Alov, E. M.; Kobylinsky, D. B.; Ermolaeva, V. V. Synthesis of Novel Five-Membered Nitrogencontaining Heterocyclic Compounds from Derivatives of Arylsulfonyl and Arylthioacetic and Propionic Acids. Chem. Heterocycl. Compd. 2001, 37, 1102–1106. DOI: 10.1023/A:1013275515682.
   Google Scholar
• Ledeţi, I.; Bercean, V.; Alexa, A.; Şoica, C.; Şuta, L.-M.; Dehelean, C.; Trandafirescu, C.; Muntean, D.; Licker, M.; Fuliaş, A. Preparation and Antibacterial Properties of Substituted 1,2,4-Triazoles. J. Chem. 2015, 2015, 1–5. DOI: 10.1155/2015/879343.
   Web of Science ®Google Scholar
• Garratt, P. J. Apractical Methylation Procedure for (1H)-1,2,4-Trazole. In: Comprehensive Heterocyclic Chemistry; II; Katritzky, A.R.; Rees, C.W.; Sriven, E.F.V., Eds.; Elsevier: Oxford, 1996, Vol. 4; pp. 127–163.
   Google Scholar
• Turnbull, K. Five-Membered Ring Systems with More than One Nitrogen Atom. In Progress in Heterocyclic Chemistry; Gribble, G.W.; Joule, J.A., Eds.;Elsevier: Oxford, 1998; Vol. 10; pp. 153–171. DOI: 10.1016/S0959-6380(98)80010-X.
   Google Scholar
• Balasubramanian, M.; Keay, J. G.; Scriven, E. FV.; Shobana, N. Approches to the Synthesis of 1-Substituted 1,2,4-Triazoles. Heterocycles 1994, 37, 1951–1975. DOI: 10.3987/REV-93-SR11.
   Web of Science ®Google Scholar
• Angulo, J.; Serrano, M.; Henning, L. Synthesis and Characterization of 1,5-Diphenyl-1,2,4-Triazole-Thion. Rev. Soc. Quim. Peru 2003, 69, 131–142.
   Google Scholar
• Yavari, I.; Shirgahi-Talari, F.; Hossaini, Z.; Sabbaghan, M.; Seyfi, S. Synthesis of Functionalized 1,2,4-Triazole-3-Thiones from Ammonium Isothiocyanate, Acid Chlorides, and Arylhydrazines. Mol. Divers. 2010, 14, 763–766. DOI: 10.1007/s11030-009-9218-9.
   PubMed Web of Science ®Google Scholar
• Wirth, T. Organoselenium Chemistry: synthesis and Reactions; Wiley-VCH: Weinheim, Germany; 2012; pp. 1–51.
   Google Scholar
• Sydnes, M. O.; Isobe, M. Exclusive Formation of Azo-Compounds upon Hydrogenolysis of Nitrobenzeneseleninic Acid Derivatives over Pd/C. Monatsh. Chem. 2015, 146, 351–356. DOI: 10.1007/s00706-014-1373-8.
   Web of Science ®Google Scholar
• Razus, A. C.; Birzan, L.; Hanganu, A.; Cristea, M.; Ungureanu, E.-M.; Soare, M.-L.; Buica, G.-O. 1-Phenylselanylazulenes: synthesis and Selenium Atom Oxidation. Monatsh. Chem. 2014, 145, 1999–2009. DOI: 10.1007/s00706-014-1297-3.
   Web of Science ®Google Scholar
• Rvovic, M. D.; Divac, V. M.; Jankovic, N. Z.; Bugarcic, Z. M. Cyclization of Some Terpenic Alcohols by Phenylselenoetherification Reaction. Monatsh. Chem. 2013, 144, 1227–1231. DOI: 10.1007/s00706-013-1006-7.
   Web of Science ®Google Scholar
• Filipovic, N.; Polovic, N.; Raskovic, B.; Misirlic-Dencic, S.; Dulovic, M.; Savic, M.; Niksic, M.; Mitic, D.; Andelkovic, K.; Todorovic, T. Biological Activity of Two Isomeric N-Heteroaromatic Selenosemicarbazones and Their Metal Complexes. Monatsh. Chem. 2014, 145, 1089–1099. DOI: 10.1007/s00706-014.
   Web of Science ®Google Scholar
• Mosslemin, M. H.; Anary-Abbasinejad, M.; Hassanabadi, A.; Bagheri, M. A. Three-Component Reaction between Triphenylphosphine, Dialkyl Acetylenedicarboxylate and 4-Amino-5-Alkyl-2,4-Dihydro-1,2,4-Triazole-3-Thiones: An Efficient One-Pot Synthesis of Stable Phosphorus Ylides. J. Sulfur Chem. 2010, 31, 135–139. DOI: 10.1080/17415991003682617.
   Web of Science ®Google Scholar
• Hassanabadi, A.; Mosslemin, M. H.; Tadayonfar, S. E. Three-Component Reaction between 4-Hydroxycoumarin, Ammonium Thiocyanate and Acid Chlorides in the Presence of N-Methylimidazole under Solvent-Free Conditions. J. Chem. Res. 2011, 35, 29–31. DOI: 10.3184/174751911X556729.
   Google Scholar
• Yavari, I.; Mosaferi, S. A One-Pot Synthesis of 2H-Pyrido[1,2-a][1,3,5]Triazine-2-Selenones from Acyl Isoselenocyanates and Pyridin-2-Amine. Monatsh. Chem. 2017, 148, 963–966. DOI: 10.1007/s00706-016-1834-3. DOI: 10.1007/s00706-016-1834-3.
   Web of Science ®Google Scholar