194809-95-5Relevant academic research and scientific papers
A novel approach to bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes: Via the [3 + 2]-dipolar cycloaddition of imidazole N -oxides and 2-heteroaryl-3,3-dimethylacrylonitriles
Kutasevich, Anton V.,Niktarov, Anton S.,Uvarova, Ekaterina S.,Karnoukhova, Valentina A.,Mityanov, Vitaly S.
, p. 8988 - 8998 (2021/11/09)
A new synthetic approach for obtaining previously unknown bis(1,3-azol-2-yl)acetonitriles and bis(1,3-azol-2-yl)methanes has been developed. It is based on 1,3-dipolar cycloaddition between 2-unsubstituted imidazole N-oxides and 2-(1,3-azol-2-yl)-3,3-dimethylacrylonitriles, which are easily available through the condensation of (1,3-azol-2-yl)acetonitriles with acetone. The method allows for the construction of various unsymmetric derivatives based on imidazole, oxazole, thiazole, and 1,3,4-thiadiazole cyclic molecules. Its potential has been demonstrated via the synthesis of 24 diverse derivatives with yields of 29-92%. Bis(1,3-azol-2-yl)acetonitriles can be converted to the corresponding bis(1,3-azol-2-yl)methanes via simple acid hydrolysis followed by subsequent spontaneous decarboxylation at nearly quantitative yields.
A Convenient Synthesis of Thiophene,1,3-Thiazole,2,3-Dihydro-1,3,4-thiadiazole and Pyrazole Derivatives.
Abdelbamid, Abdon O.,Al-Shehri, Sead M.
, p. 1681 - 1694 (2007/10/03)
Thiazole 3 reacts with benzaldehyde, p-tolualdehyde, salicylaldehyde, benzenediazonium chloride and aryl isothiocyanates to afford 4a, 4b, 5, 9 and 10a, b, respectively. 10a reacted with a-haloesters, a-haloketones, chloroacetonitrile and hydrazonoyl halides to give aminothiophenes 13, 15, 16 and 2,3-dihydro-1,3,4-thiadiazoles 21, 27, respectively.Aminopyrazole 19 was prepared via reaction of S-methyl 18 with hydrazine hydrate.Substituted pyrazoles 29 were obtained through the reaction of hydrazonoyl halides and 2-oxosulfones 28 in ethanolic sodium ethoxide solution.. 2, 3-Dihydrothiadiazoles 33 were synthesised by the reaction of 28 with a mixture of aryl isothiocyanates and hydrazonoyl halides.All the structures were confirmed by elemental analyses and spectral data.
