Reaction of Phenylhydrazides of N-Acyl-β-phenyl-β-alanine with Phosphorus Oxychloride

Article abstract of DOI:10.1007/BF00496603

The reaction of N'-methyl-N'-phenylhydrazides of N-acyl-β-phenyl-β-alanine with phosphorus oxychloride is accompanied by cleavage of the C-N bond in the intermediately formed 2-aminoindole derivative and, after splitting out of an amide fragment, leads to 1-methyl-3-benzylidene-2-iminoindoline and nitriles.Pyrimido<4,5-b>indoles - products of cyclization of the corresponding intermediate 2-aminoindole derivatives - were isolated from the reaction mixtures in low yields.The structure of 1-methyl-3-benzylidene-2-iminoindoline was proved by alternative synthesis.