SYNTHESIS AND CONFORMATIONAL STUDY OF BETA-HYDROXY SULFONES, BIOISOSTERES OF OXISURAN METABOLITES, AND THEIR O-METHYL DERIVATIVES

The synthesis and conformational analysis of 2-(methylsulfonyl)-1-(2-q uinolyl)ethanol, 2-(methylsulfonyl)-1-(1-isoquinolyl)ethanol, 2-(methy lsulfonyl)-1-(2-pyrazinyl)ethanol, and the O-methyl derivatives, -(met hylsulfonyl)-1-(methoxy)-1-(2-quinolyl)ethane and thylsulfonyl)-1-(met hoxy)-1-(1-isoquinolyl)ethane, are reported. The conformational analys is of beta-hydroxy sulfones and beta-methoxy sulfones has been carried out from the observed vicinal coupling constants, using molecular mec hanics force field (MMX) and the Altona relationship as fundamental to ols. Polar interactions are the main factors that control the stabilit y of the different conformations being the steric effects and intramol ecular hydrogen bonding less important contributions. Copyright (C) 19 96 Published by Elsevier Science Ltd