A. S. Shawali, A. Osman
1971
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Influential Citations
117
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Quality indicators
Journal
Tetrahedron
Abstract
Abstract The preparation and spectral properties of 18 phenylcarbamoylarylhydrazidic chlorides (IIa-r) derived from coupling of diazotized anilines to α-chloroacetoacetanilide have been investigated. Reaction of these hydrazidic chlorides with various nucleophiles results in ready substitution of the chlorine atom. In particular, reaction of II with primary or secondary amines proved an effective method for the preparation of oxanilamidrazones (IV–VIII). A number of II reacted with NaCN and NaOPh to yield arylazo derivatives of cyanoacetanilide and phenoxyacetanilide, respectively. Treatment of IIa with MeMgl gives pyruvanilide phenylhydrazone. Reaction of IIa with NaOAc gives, XIII through OAc → NAc rearrangement. Structural assignments have been made on the basis of IR and UV spectra and independent synthesis wherever possible.