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Issue 16, 2014
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Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles

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Abstract

The intramolecular 1,3-dipolar cycloaddition of isovanillin derived N-aryl hydroxylamines possessing ortho-allylic dipolarophiles affords novel benzo analogues of tricyclic isoxazolidines that can be readily transformed into functionalized lactams, γ-aminoalcohols and oxazepines. The corresponding N-unsubstituted hydroxylamines give rise to tetrahydroisoquinolines. Anxiogenic properties of these compounds are tested in zebra fish.

Graphical abstract: Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles

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Publication details

The article was received on 10 Dec 2013, accepted on 29 Jan 2014 and first published on 29 Jan 2014


Article type: Paper
DOI: 10.1039/C3OB42460J
Citation: Org. Biomol. Chem., 2014,12, 2552-2558
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    Isovanillin derived N-(un)substituted hydroxylamines possessing an ortho-allylic group: valuable precursors to bioactive N-heterocycles

    B. Dulla, N. D. Tangellamudi, S. Balasubramanian, S. Yellanki, R. Medishetti, R. Kumar Banote, G. Hari Chaudhari, P. Kulkarni, J. Iqbal, O. Reiser and M. Pal, Org. Biomol. Chem., 2014, 12, 2552
    DOI: 10.1039/C3OB42460J

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