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New oxazilines with sulfolane frame

Iryna S. Zarovna, Iryna V. Sadkova, Ivan V. Kulakov, Petr G. Dulnev, Vitaliy A. Palchikov

Abstract


Oxazolines are widely used as synthons for medicines and their production, as protection for structural fragments of reaction centers, as well as ligands. We for the first time examined the ability of cis- and trans-3-hydroxy-4-aminosulfolanov to form oxazolines. Oxazolines are formed by cyclization of the corresponding N-acyl derivatives of trans-3-hydroxy-4-aminosulfolan under reflux in thionyl chloride; amides of cis-isomer aminoalcohol under the same conditions of the reaction do not formed identically product. These results confirm that the oxazoline cycle formed by realization of intramolecular SN2- mechanism using thionyl chloride as dehydrating agent; alternative mechanism (the attack of the hydroxyl group on carbon of amide group) can not be realized using the microwave radiation reaction mass.

Keywords


sulfolane; aminotetragidrotiofen-4-3-ol-1,1-dioxide; the aminoalcohol; 1,3-oxazolin; amide

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DOI: http://dx.doi.org/10.15421/081315

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