Free accessResearch articleFirst published online 2017-6
One-Step Synthesis of 2-Alkenecarbodithioate Esters from Substituted Propargyl Ethers,and Their Conversion into Isothiazole Ring through a [4+1] Type Oxidative Ring Closure
Treatment of substituted propargyl methyl ethers with a base and elemental sulfur in the presence of a thiolate ion afforded 2-alkenecarbodithioate esters in good yields. The reaction is assumed to proceed through a pathway involving in situ generation of propadienethione intermediates. Further conversion of 2-alkenecarbodithioate esters into 2,3-dihydroisothiazoles were efficiently performed by treating with chloramine-T through a [4+1] type oxidative ring closure via thiocarbonyl S-tosylimides.
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