303023-87-2

Upstream product

• 61767-26-8 N-(2,2-dichloro-1-cyanovinyl)-4-methylbenzamide 

Downstream Products

• 845258-50-6 C₁₈H₁₅N₅OS 
• 1028193-19-2 C₁₅H₁₅N₅O₃S 
• 1028193-20-5 C₁₉H₁₅N₅O₂S 
• 878027-40-8 2-p-tolyl-5-(2-p-toluylhydrazino)-1,3-oxazole-4-carbonitrile 
• 1028193-27-2 C₁₅H₁₅N₅O₃S 
• 1028193-28-3 C₁₉H₁₅N₅O₂S 
• 1028193-31-8 C₁₅H₁₇N₅O₄S 
• 1028193-32-9 C₁₉H₁₇N₅O₃S 
• 371194-14-8 4-methyl-benzoic acid N-(4-cyano-2-p-tolyl-oxazol-5-yl)-hydrazide 

Relevant academic research and scientific papers

A challenging synthesis of new 1,3,4-thiadiazole derivatives starting from 2-acylamino-3,3-dichloroacrylonitriles

Available 2-acylamino-3,3-dichloro-acrylonitriles, when treated with hydrazine hydrate, provide 2-alkyl- or 2-aryl-5-hydrazino-1,3-oxazole-4- carbonitriles that readily add alkyl or aryl isothio-cyanates and the adducts formed recyclize on heating. Finally, the synthesis results in 5-alkyl(aryl)amino-1,3,4-thiadiazol-2-yl(acylamino)acetonitriles or the products of their further cyclization, 2-(5-amino-1,3-oxazol-2-yl)-1,3,4-thiadiazole derivatives. The structures of the novel substituted 1,3,4-thiadiazoles are corroborated spectroscopically as well as by X-ray diffraction method.

Recyclization of 2-aryl-4-cyano-5-hydrazinooxazoles

The available 2-benzoylamino-3,3-dichloroacrylonitrile and its analogs when treated with excess hydrazine hydrate convert to 2-aryl-4-cyano-5-hydrazinooxazoles. The products are fairly stable in usual conditions but undergo recyclization on heating in acetic acid to give previously unknown derivatives of 2-methyl-1,3,4-oxadiazole with a 5-acylamino(carbamoyl)methyl substituent, whose structure was established by spectroscopy and X-ray diffraction. An important role in this complex transformation is probably played by prototropic forms of 4-cyano-5-hydrazinooxazoles, viz. hydrazones of substituted 2-oxazolin-5-ones which are not aromatic and thus can be cleaved with acetic acid and then recyclize.