Górecki Sebastian, Kudelko Agnieszka
Department of Chemical Organic Technology and Petrochemistry, The Silesian University of Technology, Krzywoustego 4, PL-44100 Gliwice, Poland.
Molecules. 2024 Sep 11;29(18):4316. doi: 10.3390/molecules29184316.
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 ,-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 H- and C-NMR, IR, and UV-Vis spectroscopy.
描述了一种合成新型含苯基偶氮部分的有效方法。制备了5-(4-(苯基重氮基)苯基)-1,3,4-恶二唑的衍生物，其杂环骨架的2位被不同链长的烷基取代。使用适当的4-(5-烷基-1,3,4-恶二唑-2-基)苯胺获得标题化合物，将其进行重氮化，随后与苯酚、间苯二酚和N,N-二甲基苯胺偶联。此外，我们报道了一种温和有效的方法，通过使用硼氢化钠-二水合氯化亚锡作为还原体系，选择性还原相应的2-烷基-5-(4-硝基苯基)-1,3,4-恶二唑来制备4-(5-烷基-1,3,4-恶二唑-2-基)苯胺。通过氢核磁共振、碳核磁共振、红外光谱和紫外可见光谱确认了所制备化合物的化学结构。
