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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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Article information


Submitted
10 Dec 2013
Accepted
29 Jan 2014
First published
29 Jan 2014

Org. Biomol. Chem., 2014,12, 2552-2558
Article type
Paper

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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