Reactions of aromatic dithiols with diethyl 2-alkyl-2-(oxiran-2-ylmethyl)malonates

Abstract

New sulfur-containing butano-4-lactones were synthesized by reaction of diethyl 2-alkyl-2-(oxiran-2-ylmethyl)malonates with biphenyl-4,4′-dithiol, (biphenyl-4,4′-diyl)dimethanethiol, and (2,4,6-trimethylbenzene-1,3-diyl)dimethanethiol. Opening of the oxirane ring in the initial ester followed the Krasuskii rule. † Deceased.Functionally substituted butano-4-lactones constitute a promising class of organic compounds. They are widely used in fine organic synthesis and in synthesis of medicinal agents [1-3]. Therefore, development of new methods of synthesis of oxygen-, nitrogen-, and especially sulfur-containing butano-4-lactone derivatives seems to be a quite important problem, and it could considerably extend the synthetic potential and scope of application of this class of compounds [3][4][5][6][7].We previously showed that the use of alkyl(oxiran-2-ylmethyl)malonic and acetoacetic acid esters [6-9] ensures wide variation of structural fragments in butano-4-lactones and one-step syntheses of various polyfunctionalized butano-4-lactones. Reactions of