1,2-DIACYL-1-ARYLHYDRAZINES. 1. DERIVATIVES OF 2-HYDROXY- AND 2-HALOGENOBENZOIC ACIDS

Article abstract of DOI:10.1007/BF00866599

New 1,2-diacyl-1-arylhydrazines, containing a hydroxy group or a mobile halogen atom in the 1-acyl fragment, were obtained by the reaction of the arylhydrazones of acetyl and benzoyl chlorides with the salts of 2-hydroxy-, 2-acetoxy-, and 2-halogeno-3-nitrobenzoic acids. 1-(2-Hydroxybenzoyl)-1-aryl-2-acylhydrazines could not be converted into cyclic products.On heating in alkaline and acidic media elimination of the more hindered salicyloyl group and not dehydration occurred.When boiled in DMF in the presence of bases, 1-(2-halogeno-3-nitro-5-R-benzoyl)-1-aryl-2-acylhydrazines gave 2-aryl-5-R-7-nitroindazol-3-ones and not the expected 4,5-dihydrobenzo-1,3,4-oxadiazepin-5-ones. Keywords: 1,2-Diacyl-1-arylhydrazines, salicylic acid, nitrohalogenobenzoic acids, 2-aryl-7-nitroindazol-3-ones, Chattaway-Walker reaction.