Synthesis and conformational study of β-hydroxy sulfones, bioisosteres of oxisuran metabolites, and their O-methyl derivatives

The synthesis and conformational analysis of 2-(methylsulfonyl)-1-(2-quinolyl)ethanol, 2-(methylsulfonyl)-1-(1-isoquinolyl)ethanol, 2-(methylsulfonyl)-1-(2-pyrazinyl)ethanol, and the O-methyl derivatives, 2-(methylsulfonyl)-1-(methoxy)-1-(2-quinolyl)ethane and 2-(methylsulfonyl)-1-(methoxy)-1-(1-iso...

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Bibliographic Details
Published in:Tetrahedron 1996-08, Vol.52 (34), p.11239-11256
Main Authors: Alvarez-Ibarra, C., Cuervo-Rodríguez, R., Fernández-Monreal, M.C., Ruiz, M.P.
Format: Article
Language:English
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Summary:The synthesis and conformational analysis of 2-(methylsulfonyl)-1-(2-quinolyl)ethanol, 2-(methylsulfonyl)-1-(1-isoquinolyl)ethanol, 2-(methylsulfonyl)-1-(2-pyrazinyl)ethanol, and the O-methyl derivatives, 2-(methylsulfonyl)-1-(methoxy)-1-(2-quinolyl)ethane and 2-(methylsulfonyl)-1-(methoxy)-1-(1-isoquinolyl)ethane, are reported. The conformational analysis of β-hydroxy sulfones and β-methoxy sulfones has been carried out from the observed vicinal coupling constants, using a molecular mechanics force field (MMX) and the Altona relationship as fundamental tools. Polar interactions are the main factor that control the stability of the different conformations being the steric effects and intramolecular hydrogen bonding less important contributions. Conformational analysis has been carried out from the observed vicinal coupling constants ( 3J) using a molecular mechanics force field (MMX) and the Altona relationship as fundamental tools.
ISSN:0040-4020
1464-5416
DOI:10.1016/0040-4020(96)00650-3