Abstract
Cyclic sulfones and their derivatives have vast applications in biological, pharmaceutical, medicinal and in many other fields. Herein, we report synthesis of ten new hydroxyimines bearing sulfolane moiety by reaction of cis- and trans-amino alcohols with aromatic aldehydes. An extensive spectroscopic characterization of the products, using 1D and 2D NMR techniques (1H, 13C, NOE, NOESY, COSY, HSQC, HMBC) showed ring-chain tautomerism in deuterochloroform solution for cis-hydroxyimines. The content of the cyclic (1,3-oxazolidine) form increases with increasing electron-withdrawing strength of the substituent in the para position of the benzene ring of the imine. The structure of cis-(3S,4R)-3-hydroxy-4-((E)-(2-hydroxybenzylidene)amino)tetrahydrothiophene 1,1-dioxide was confirmed using XRD analysis. In addition, ADMET properties of products were evaluated in silico and showed high drug similarity.
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