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JOURNALS // Mendeleev Communications // Archive

Mendeleev Commun., 2024 Volume 34, Issue 1, Pages 122–125 (Mi mendc62)

Communications

Synthesis of hybrid molecules based on thioglycolurils and 1,2,5-oxadiazoles via the Eschenmoser sulfide contraction

E. E. Vinogradova, A. A. Larin, G. A. Gazieva

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: A simple synthesis of novel hybrid molecules containing methylidenehexahydroimidazo[4,5-d]imidazol-2(1H)-one and 1,2,5-oxadiazole moieties is based on the Eschenmoser sulfide contraction involving alkylative precoupling of thioglycolurils with 3(4)-bromoacetyl-1,2,5-oxadiazoles. The proposed method does not require using toxic PPh3 for sulfur extrusion. The synthesized compounds may serve as platforms for constructing both new bioactive and new high- energy compounds.

Keywords: glycoluril, thioglycoluril, furazan, furoxan, Eschenmoser sulfide contraction.

Language: English

DOI: 10.1016/j.mencom.2024.01.037



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