{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,11]],"date-time":"2026-08-11T03:46:16Z","timestamp":1786419976668,"version":"build-2736575974"},"reference-count":57,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2020,11,20]],"date-time":"2020-11-20T00:00:00Z","timestamp":1605830400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this study, a novel 1,3,4-thiadiazole derivative containing 3-mercaptobutan-2-one and quinazolin-4-one moieties (Compound 3) is synthesized by the coupling of 2-amino-1,3,4-thiadiazole-5-(3-mercaptobutan-2-one) (Compound 1) with 2-Phenyl-4H-3,1-benzoxazin-4-one (Compound 2) in one molecule moiety. Compound 3 is found to exist as two types of intra-molecular hydrogen bonding with keto-enol tautomerism characters, which is further confirmed using FTIR, 1H-NMR, 13C-NMR, mass spectrometer, and UV-Visible spectra. The 1H-NMR and UV-Visible spectra of Compound 3 are investigated in different solvents such as methanol, chloroform, and DMSO. Compound 3 exhibits keto-enol tautomeric forms in solvents with different percentage ratios depending on the solvent polarity. The 1H-NMR and UV-Visible spectral results show that Compound 3 favors the keto over the enol form in polar aprotic solvents such as DMSO and the enol over the keto form in non-polar solvents such as chloroform. The 13C-NMR spectrum gives two singles at \u03b4 204.5 ppm, due to ketonic carbon, and \u03b4 155.5 ppm, due to enolic carbon, confirming the keto-enol tautomerism of Compound 3. Furthermore, the molecular ion at m\/z 43 and m\/z 407 in the mass spectrum of Compound 3 and fragmentation mechanisms proposed reveal the existence of the keto and enol forms, respectively.<\/jats:p>","DOI":"10.3390\/molecules25225441","type":"journal-article","created":{"date-parts":[[2020,11,20]],"date-time":"2020-11-20T09:46:18Z","timestamp":1605865578000},"page":"5441","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Synthesis, Spectroscopic Studies and Keto-Enol Tautomerism of Novel 1,3,4-Thiadiazole Derivative Containing 3-Mercaptobutan-2-one and Quinazolin-4-one Moieties"],"prefix":"10.3390","volume":"25","author":[{"given":"Sewara J.","family":"Mohammed","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, University of Sulaimani, Qlyasan Street, Kurdistan Regional Government, Sulaimani 46002, Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akam K.","family":"Salih","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, University of Sulaimani, Qlyasan Street, Kurdistan Regional Government, Sulaimani 46002, Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammad Amin M.","family":"Rashid","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, University of Sulaimani, Qlyasan Street, Kurdistan Regional Government, Sulaimani 46002, Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6866-4116","authenticated-orcid":false,"given":"Khalid M.","family":"Omer","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, University of Sulaimani, Qlyasan Street, Kurdistan Regional Government, Sulaimani 46002, Iraq"},{"name":"Komar Research Center (KRC), Komar University of Science and Technology, Kurdistan Regional Government, Sulaimani 46002, Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karzan A.","family":"Abdalkarim","sequence":"additional","affiliation":[{"name":"Department of Chemistry, College of Science, University of Sulaimani, Qlyasan Street, Kurdistan Regional Government, Sulaimani 46002, Iraq"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,11,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Taylor, P.J., Van Der Zwan, G., and Antonov, L. 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