Synthesis and stereochemistry of new 1,3-thiazolidine systems based on 2-amino-2-(mercaptomethyl)propane-1,3-diol: 4,4-bis(hydroxymethyl)-1,3-thiazolidines and c-5-hydroxymethyl-3-oxa-7-thia-r-1-azabicyclo[3.3.0]octanes☆

Add time:08/26/2019    Source:sciencedirect.com

The thiaminalisation of 2-amino-2-(mercaptomethyl)propane-1,3-diol [‘2-(hydroxymethyl)cysteinol’] with aryl(di)aldehydes is reported. The resulting new class of 2-aryl-4,4-bis(hydroxymethyl)-1,3-thiazolidines is investigated by NMR and IR spectroscopy in tandem with DFT calculations, permitting structural assignments that are discussed in terms of conformational analysis, anomeric effects and ring-chain tautomerism. These acquired data are subsequently exploited. After treatment with formaldehyde, the subsequent (double) regio- and diastereoselective oxaminalisation of the 1,3-thiazolidine building-block affords the first non-symmetric series of a thiazolidin-oxazolidine fused system singly functionalised at the C-5 position. An unexpected rearrangement, which consists of the partial relocation of the Ar ligand from the 1,3-thiazolidine to the 1,3-oxazolidine ring, is observed as a major influence on the substitution of the Ar ring. The first single crystal X-ray analysis of the title bicyclic system, which discloses the homo- and/or heterochiral non-bonding interactions, is also presented.

We also recommend Trading Suppliers and Manufacturers of 1,3-BIS(4-BROMOPHENYL)-5,5-DIETHOXY-2,4-IMIDAZOLIDINEDIONE (cas 113567-53-6). Pls Click Website Link as below: cas 113567-53-6 suppliers

Prev:Direct synthesis of 2-aryl-1,3-benzoselenazoles by reaction of bis(2-aminophenyl) diselenides with aryl aldehydes using sodium metabisulfite
Next:1,3-Bis(4-methoxyphenyl)cyclohexane-1,3-diyl cation radical: divergent reactivity depending upon electron-transfer conditions)