Novel ring chemistry of vitamin B6 with singlet oxygen and an activated ene: isolated products and identified intermediates suggesting an operable [3 + 2] cycloaddition

Pyridoxine reaction with (1)O(2) in aqueous solution at neutral pH resulted in oxidation at the 2- and 6-positions of the pyridine ring and unprecedented ring contraction. Kinetic and low temperature studies provided observable intermediates by NMR spectroscopy. In addition, novel cycloaddition betw...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-09, Vol.10 (36), p.7278-7281
Main Authors: Samuel, David, Norrell, Kirsten, Hilmey, David G
Format: Article
Language:English
Subjects:
Cyclization
Ketones - chemical synthesis
Ketones - chemistry
Models, Molecular
Molecular Structure
Singlet Oxygen - chemistry
Vitamin B 6 - chemistry
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Summary:Pyridoxine reaction with (1)O(2) in aqueous solution at neutral pH resulted in oxidation at the 2- and 6-positions of the pyridine ring and unprecedented ring contraction. Kinetic and low temperature studies provided observable intermediates by NMR spectroscopy. In addition, novel cycloaddition between pyridoxine and N-methylmaleimide, without N-alkylation and in water, suggest a common [3 + 2] cycloaddition with the 3-hydroxypyridine ring.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26067k