Synthesis of 1,3,4-thiadiazol-2(3H)-one derivatives via an unexpected intramolecular addition-elimination reaction of 1,3,4-thiadiazoles

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dc.authoridTAHTACI, HAKAN/0000-0002-1557-6315
dc.authoridkarakurt, tuncay/0000-0001-6944-9883
dc.contributor.authorTahtaci, Hakan
dc.contributor.authorEr, Mustafa
dc.contributor.authorKarakurt, Tuncay
dc.contributor.authorSancak, Kemal
dc.date.accessioned2024-09-29T16:00:48Z
dc.date.available2024-09-29T16:00:48Z
dc.date.issued2017
dc.departmentKarabük Üniversitesien_US
dc.description.abstractA new synthesis was developed for 1,3,4-thiadiazol-2(3H)-one derivatives, based on a new arrangement on the thiadiazole ring with an intramolecular addition-elimination reaction. To this end, starting from 5-methyl-1,3,4-thiadiazole-2-thiol (1), derivatives of 3-((un)substituted benzyl)-5-methyl-1,3,4-thiadiazol-2(3H)-one (7a-g) and ((un)substituted phenyl)-2-oxoethyl)-5-methyl,3,4-thiadiazol-2(3H)-one (10-15) were synthesized (in yields of 81-88% and 63-71%, respectively). The structures of all synthesized compounds were characterized using IR, H-1 NMR, and C-13 NMR spectroscopy, and elemental analysis, mass spectroscopy and X-ray diffraction analysis (compounds 3c, 7b-f and 10) techniques. This study presents a new and effective reaction path for the synthesis of 1,3,4-thiadiazol-2(3H)-one derivatives. (C) 2017 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipKarabuk University [KBU-BAP-15/1-DS-021, KBU-BAP-17-BM-132]en_US
dc.description.sponsorshipThe financial support under the contract (KBU-BAP-15/1-DS-021 and KBU-BAP-17-BM-132) from Karabuk University is gratefully acknowledged.en_US
dc.identifier.doi10.1016/j.tet.2017.06.006
dc.identifier.endpage4425en_US
dc.identifier.issn0040-4020
dc.identifier.issue30en_US
dc.identifier.scopus2-s2.0-85020697875en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage4418en_US
dc.identifier.urihttps://doi.org/10.1016/j.tet.2017.06.006
dc.identifier.urihttps://hdl.handle.net/20.500.14619/5372
dc.identifier.volume73en_US
dc.identifier.wosWOS:000405158500022en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedronen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject1,3,4-Thiadiazoleen_US
dc.subject1,3,4-Thiadiazol-2(3H)-oneen_US
dc.subjectIntramolecular addition-elimination reactionen_US
dc.subjectA novel methoden_US
dc.titleSynthesis of 1,3,4-thiadiazol-2(3H)-one derivatives via an unexpected intramolecular addition-elimination reaction of 1,3,4-thiadiazolesen_US
dc.typeArticleen_US

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