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Issue 36, 2012
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Novel ring chemistry of vitamin B6 with singlet oxygen and an activated ene: isolated products and identified intermediates suggesting an operable [3 + 2] cycloaddition

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Abstract

Pyridoxine reaction with 1O2 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.

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

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Publication details

The article was received on 03 Jun 2012, accepted on 07 Aug 2012 and first published on 08 Aug 2012


Article type: Communication
DOI: 10.1039/C2OB26067K
Citation: Org. Biomol. Chem., 2012,10, 7278-7281
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    Novel ring chemistry of vitamin B6 with singlet oxygen and an activated ene: isolated products and identified intermediates suggesting an operable [3 + 2] cycloaddition

    D. Samuel, K. Norrell and D. G. Hilmey, Org. Biomol. Chem., 2012, 10, 7278
    DOI: 10.1039/C2OB26067K

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