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Issue 7, 2018
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Substrate selective synthesis of indole, tetrahydroquinoline and quinoline derivatives via intramolecular addition of hydrazones and imines

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Abstract

A transition-metal-free, substrate selective synthesis of 2,3-diaryl indoles has been developed via the intramolecular addition of hydrazones (bearing no α-H, derived from 2-aminobenzophenones and phenylhydrazines) to in situ generated imine intermediates. However, the hydrazones derived from 2-aminoacetophenones (bearing α-H) produced the corresponding 4-hydrazono-tetrahydroquinolines in a substrate selective manner under the optimized reaction conditions at room temperature. Moreover, differently substituted quinoline derivatives were obtained from the nucleophilic addition of in situ generated enamines derived from ketones and (E)-2-(aryl/methyl(2-phenylhydrazono)methyl)anilines.

Graphical abstract: Substrate selective synthesis of indole, tetrahydroquinoline and quinoline derivatives via intramolecular addition of hydrazones and imines

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Publication details

The article was received on 13 Dec 2017, accepted on 19 Jan 2018 and first published on 19 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QO01115F
Citation: Org. Chem. Front., 2018,5, 1170-1175
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    Substrate selective synthesis of indole, tetrahydroquinoline and quinoline derivatives via intramolecular addition of hydrazones and imines

    R. K. Maurya, O. P. S. Patel, D. Anand and P. P. Yadav, Org. Chem. Front., 2018, 5, 1170
    DOI: 10.1039/C7QO01115F

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