Synthesis and Characterization of Novel Heterocyclic Chalcones from 1-Phenyl-1H-pyrazol-3-ol

Molecules

Eglė Arbačiauskienė¹  Vaida Milišiūnaitė¹  Algirdas Šačkus¹  Elena Plytninkienė¹  Arminas Urbonavičius¹  Graziana Fortunato¹  Sonata Krikštolaitytė¹  Emilija Ambrazaitytė¹  Renzo Luisi²  Aurimas Bieliauskas³ 

[1] Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų Pl. 19, 50254 Kaunas, Lithuania;Department of Pharmacy—Drug Sciences, University of Bari “Aldo Moro”, Via E. Orabona 4, 70125 Bari, Italy;Institute of Synthetic Chemistry, Kaunas University of Technology, K. Baršausko g. 59, 51423 Kaunas, Lithuania;

关键词: Claisen–Schmidt condensation;    heterocyclic chalcones;    pyrazole;    pyridine;    1,2-oxazole (isoxazole);    ¹⁵N-labeled 1,2-oxazole;   

DOI  :  10.3390/molecules27123752

来源: DOAJ

【 摘 要 】

An efficient synthetic route to construct diverse pyrazole-based chalcones from 1-phenyl-1H-pyrazol-3-ols bearing a formyl or acetyl group on the C4 position of pyrazole ring, employing a base-catalysed Claisen–Schmidt condensation reaction, is described. Isomeric chalcones were further reacted with N-hydroxy-4-toluenesulfonamide and regioselective formation of 3,5-disubstituted 1,2-oxazoles was established. The novel pyrazole-chalcones and 1,2-oxazoles were characterized by an in-depth analysis of NMR spectral data, which were obtained through a combination of standard and advanced NMR spectroscopy techniques.

【 授权许可】

Unknown