1087-36-1Relevant academic research and scientific papers
Study on DDQ-promoted synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles from acid hydrazides and aldehydes
Jasiak, Karolina,Kudelko, Agnieszka,Zieliński, Wojciech,Ku?nik, Nikodem
, p. 87 - 106 (2017/02/23)
A facile stepwise synthesis of 2, 5-disubstituted 1, 3, 4-oxadiazoles proceeding via oxidative cyclization of N-acylhydrazones is reported. The reaction is efficiently promoted by 2, 3-dichloro-5, 6-dicyano-1, 4- benzoquinone (DDQ) to afford the desired products mostly in high yields and in relatively short times. The final 1, 3, 4-oxadiazole derivatives are also synthesized directly from acid hydrazides and aldehydes in a one-pot procedure. The substrate scope and limitations of the reported transformation are discussed in detail.
Efficient oxidative cyclisation of acid hydrazides to 2,5-disubstituted 1,3,4-oxadiazoles catalysed by Bu4NI with t-BuOOH as oxidant
Gao, Peng,Wei, Yunyang
, p. 506 - 510 (2013/09/12)
Acid hydrazides or araldehyde N-acylhydrazones can be converted in good yields to, respectively, symmetrical or unsymmetrical, 2,5-disubstituted 1,3,4-oxadiazoles at 60 °C by a Bu4NI-catalysed procedure which requires the presence of a base and 2.5 equiv. of t-butyl hydroperoxide.
Design of semicarbazones and their bio-isosteric analogues as potential anticonvulsants
Pandeya,Manjula,Stables
, p. 121 - 124 (2007/10/03)
A series of semicarbazones and hydrazones were prepared and evaluated for anticonvulsant activity. Some compounds provided significant protection against maximal electroshock (MES) and subcutaneous strychnine induced seizures (ScSty). Compound 2a emerged as the most active compound at a dose of 30 mg/kg in ScSty test. The compounds 1a, 1g and 2a-e showed significant potentiation of sedative and hypnotic activity of pentobarbitone sodium. Thus compound 2a could serve as a prototype for future developments.
Oxidation of Arylacetylhydrazones of Carbonyl Compounds with Lead Tetraacetate
Stephanidou-Stephanatou, J.,Lefkopoulou, S.
, p. 705 - 711 (2007/10/02)
Oxidation of the title compounds 8, 9 with lead tetraacetate at room temperature gives a variety of products depending on the substituents on the carbonyl carbon atom.Thus, on oxidation of the aldehyde derivatives 8 1,3,4-oxadiazolo derivatives 10 are obtained in good yields.However in some cases formation of N-acetyl-N-arylacetyl-N'-benzoylhydrazines 11 is also observed, whereas oxidation of the ketone hydrazones 9 gives in good yields the 2H,5H-1,3,4-oxadiazoles 15 or substituted monoacetoxy- 17 and diacetoxyalkanes 18.The reaction mechanisms are also discussed.
