Issue 2, 1989
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Allenes. Part 49. 4-Amino-2-(1-hydroxyalkyl)quinolines from phenylhydroxylamine and allenic nitrites

Stephen R. Landor,   Z. Tanee Fomum,   P. Forche Asobo,   Phyllis D. Landor  and  Andrew Johnson  

Abstract

Allenic nitriles, when heated with phenylhydroxylamine in ethanol for 24 h, form the intermediate 2-alkylidene-4-amino-1,2-dihydro-1-hydroxyquinolines (4) which rearrange spontaneously by a 1,3-hydroxy shift to 4-amino-2-(1-hydroxyalkyl)quinolines. The 1-hydroxyquinoline intermediate (4) does not isomerise to 2-alkyl-4-aminoquinoline 1-oxide by a 1,4-proton shift as shown by an independent synthesis of the latter. Phenylpropynenitrile with phenylhydroxylamine gave 8% of 4-amino-2-(2-hydroxyphenyl)quinoline (15).

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Article information

DOI
https://doi.org/10.1039/P19890000251
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 251-254

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Allenes. Part 49. 4-Amino-2-(1-hydroxyalkyl)quinolines from phenylhydroxylamine and allenic nitrites

S. R. Landor, Z. T. Fomum, P. F. Asobo, P. D. Landor and A. Johnson, J. Chem. Soc., Perkin Trans. 1, 1989, 251 DOI: 10.1039/P19890000251

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