Jump to main content
Jump to site search

Issue 36, 2012
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
03 Jun 2012
Accepted
07 Aug 2012
First published
08 Aug 2012

Org. Biomol. Chem., 2012,10, 7278-7281
Article type
Communication

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

Social activity

Search articles by author

Spotlight

Advertisements