Novel ring chemistry of vitamin B(6) with singlet oxygen and an activated ene: isolated products and identified intermediates suggesting an operable [3 + 2] cycloaddition |
| |
Authors: | David Samuel Kirsten Norrell David G Hilmey |
| |
Affiliation: | Department of Chemistry, St. Bonaventure University, St. Bonaventure, NY 14778, USA. dhilmey@sbu.edu. |
| |
Abstract: | 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. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|