{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,18]],"date-time":"2026-03-18T06:44:16Z","timestamp":1773816256368,"version":"3.50.1"},"reference-count":66,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2024,9,11]],"date-time":"2024-09-11T00:00:00Z","timestamp":1726012800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100007835","name":"Silesian University of Technology","doi-asserted-by":"publisher","award":["04\/050\/BK_24\/0191"],"award-info":[{"award-number":["04\/050\/BK_24\/0191"]}],"id":[{"id":"10.13039\/501100007835","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>An efficient method for the synthesis of novel phenylazo-containing moieties is described. The derivatives of 5-(4-(phenyldiazenyl)phenyl)-1,3,4-oxadiazole, substituted at position 2 of the heterocyclic scaffold with alkyl groups of different chain lengths, were prepared. The titled compounds were obtained using the appropriate 4-(5-alkyl-1,3,4-oxadiazol-2-yl)anilines, which were directed to diazotization and subsequently coupled to phenol, resorcinol, and N,N-dimethylaniline. Additionally, we report a mild and effective procedure for the preparation of 4-(5-alkyl-1,3,4-oxadiazol-2-yl)anilines via the selective reduction of the corresponding 2-alkyl-5-(4-nitrophenyl)-1,3,4-oxadiazoles using sodium borohydride-tin(II) chloride dihydrate as the reducing system. The chemical structures of the prepared compounds were confirmed by 1H- and 13C-NMR, IR, and UV-Vis spectroscopy.<\/jats:p>","DOI":"10.3390\/molecules29184316","type":"journal-article","created":{"date-parts":[[2024,9,11]],"date-time":"2024-09-11T10:33:01Z","timestamp":1726050781000},"page":"4316","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis and Characterization of Novel 2-Alkyl-1,3,4-Oxadiazoles Containing a Phenylazo Group"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-4426-6528","authenticated-orcid":false,"given":"Sebastian","family":"G\u00f3recki","sequence":"first","affiliation":[{"name":"Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6949-4246","authenticated-orcid":false,"given":"Agnieszka","family":"Kudelko","sequence":"additional","affiliation":[{"name":"Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,9,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2372","DOI":"10.1016\/j.ejmech.2008.09.005","article-title":"Aroylpropionic Acid Based 2,5-Disubstituted-1,3,4-Oxadiazoles: Synthesis and Their Anti-Inflammatory and Analgesic Activities","volume":"44","author":"Akhter","year":"2009","journal-title":"Eur. 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