Doughty, Michael B.; Risinger, G. E.; Jungk, Steven J. published the artcile< Chemistry of the tricyclic form of thiamin with aldehydes in basic ethanol>, COA of Formula: C7H9NO2S, the main research area is thiamin aldehyde reaction; hydroxybenzylthiamin; pyrimidinylmethylfurothiazole; furothiazole pyrimidinylmethyl.
Upon the addition of PhCHO to basic thiamin solution gives an intermediate accumulates which gives rise to 2-(1-hydroxyphenylmethyl)thiamin-HCl upon acidification of the reaction mixture and high yields of both 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-benzoyl-3a-methylperhydrofuro[2,3-d]thiazole and benzoin when the reaction mixture is stirred for 5 h. Given that thiamin is unstable under these conditions such that it is converted completely to its tricyclic species, the 2-(1-hydroxyalkyl)thiamin salts, which have an increased base lability due to the addition of a C-2/N-3 torsional interaction to the base-labile thiazolium ring, would also not be expected to accumulate in appreciable concentrations under identical conditions. Based on product isolation and the synthesis of 2-benzoyl-3,4-dimethyl-5-ethoxycarbonyl-[2H]-thiazoline in the reaction of 3,4-dimethyl-5-ethyoxycarbonylthiazolium iodide with PhCHO in basic MeOH, the intermediate which accumulates during the reaction of the tricyclic form of thiam with PhCHO is a 2-benzoylthiazoline in equilibrium with a low concentration of its enol isomer. Reasons for the increased catalytic power of thiamin under these conditions, as well as the relevance of this chem. to the active site chem. of thiamin pyrophosphate, are discussed.
Bioorganic Chemistry published new progress about 20582-55-2. 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, COA of Formula: C7H9NO2S.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica