Issue 3, 2006
From the journal:

Organic & Biomolecular Chemistry

Preparation of 2,3-dihydroselenolo[2,3-b]pyridines and related compounds by free-radical means†

Tahli Fenner,a   Jonathan M. Whiteab  and  Carl H. Schiesser‡*ab  

* Corresponding authors

a School of Chemistry, The University of Melbourne, Victoria, Australia

b Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Victoria, Australia
E-mail: carlhs@unimelb.edu.au
Fax: +61 3 9347 8189
Tel: +61 3 8344 2432

Abstract

Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2-(benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2-carboethoxy-2,3-dihydroselenolo[2,3-b]pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Alternatively, rearrangement of O-(ω-haloalkyl)esters 34 of 2-carboethoxy-N-hydroxypyridine-2-selone affords azonianaphthalenium halides 37 in 79% yield.

Graphical abstract: Preparation of 2,3-dihydroselenolo[2,3-b]pyridines and related compounds by free-radical means

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Article information

DOI
https://doi.org/10.1039/B515385A
Article type
Paper
Submitted
21 Oct 2005
Accepted
28 Nov 2005
First published
21 Dec 2005

Org. Biomol. Chem., 2006,4, 466-474

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Preparation of 2,3-dihydroselenolo[2,3-b]pyridines and related compounds by free-radical means

T. Fenner, J. M. White and C. H. Schiesser, Org. Biomol. Chem., 2006, 4, 466 DOI: 10.1039/B515385A

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