Abstract
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.
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Deceased.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1356–1359, October, 1980.
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Zabrodnyaya, V.G., Portnov, Y.N., Voronin, V.G. et al. Reaction of phenylhydrazides of N-acyl-β-phenyl-β-alanine with phosphorus oxychloride. Chem Heterocycl Compd 16, 1028–1031 (1980). https://doi.org/10.1007/BF00496603
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DOI: https://doi.org/10.1007/BF00496603