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Features of interaction isomeric 4-aminotetrahydrothiophen-3-ol-1,1-dioxide with some C-electrophilic reagents

Iryna S. Zarovna, Andriy V. Tokar, Vitaliy A. Palchikov

Abstract


Sulfolane-containing aminoalcohols have a variety biological activity, as well as high synthetic potential and the ability to use sulfolanе-containing building blocks in the construction of new heterocyclic systems. Interaction of cis- and trans-4-aminotetrahydrothiophen-3-ol-1,1-dioxides with N,N-carbonyldiimidazole, Boc-anhydride, ethylchloroformate gives only the bis-derivatives, that are not capable of further cyclization to oxazolidinones. On the nitrogen atom in both isomeric aminoalcohols slightly larger charge than on the oxygen atom (calculated values of the charges within the NBO-theory) that explains the formation of the bis-derivatives in the interaction with strong C-electrophiles. Thus, using multistep procedure for the synthesis heterocyclic compounds (through the formation of urethanes, Boc-derivatives, etc.) are not effective for both isomers.


Keywords


sulfolane; 4-aminotetrahydrothiophen-3-ol-1,1-dioxide; aminoalcohol

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DOI: http://dx.doi.org/10.15421/081419

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