SYNTHESIS OF SATURATED NITROGEN-CONTAINING HETEROCYCLIC SULFINATES
DOI:
https://doi.org/10.15407/dopovidi2023.05.026Keywords:
organosulfur compounds, nitrogen-containing heterocycles, sp3-enriched compounds, sulfinates, building blocksAbstract
A preparative approach to the synthesis of a series of novel saturated nitrogen-containing heterocyclic sulfinates, promising bifunctional building blocks for applications in organic and medicinal chemistry, is proposed. The method is based on the utilization of N-Boc-protected heterocyclic amino alcohols as starting materials and involves their transformation into thiopyrimidyl derivatives, subsequent oxidation, and base-promoted cleavage of the resulting sulfones. At each stage, reaction conditions were optimized with the aim of obtaining multigram quantities of the target compounds. Following minor modifications, the approach was deemed suitable for the preparation of optically pure compounds. Possible applications of the synthesized sulfinates are illustrated by their transformation into the corresponding sulfonamide derivatives.
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