The Synthesis and Base-Induced Breakdown of Triaryl 1,4-Oxathiins-An Experimental and DFT Study.

ABSTRACT: 1,4-Oxathiins are valued for a breadth of bioactivities and are known commercial fungicides. This article explores a novel preparation of 2,3,6-trisubstituted 1,4-oxathiin-S,S-dioxides via the reaction of benzyl 1-alkynyl sulfones and aryl aldehydes under basic conditions. A total of 20 examples possessing exclusively a trans arrangement of the 2,3-diaryl substituents are exhibited; the products demonstrate a variation of functional groups on the aryl ring attached to the heterocyclic ring system. The preparation is hindered by the base sensitivity of the products, and a ring-opened by-product typically contaminates the reaction mixture. A DFT assessment of the overall system includes a lithium counterion and offers possible pathways for the incorporation of the aldehyde, the cyclization s

SUBMITTER: Nicol EA 

PROVIDER: S-EPMC10489040 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature