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

[Display omitted] 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. Th...

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Bibliographic Details
Published in:Mendeleev communications 2024-01, Vol.34 (1), p.122-125
Main Authors: Vinogradova, Ekaterina E., Larin, Alexander A., Gazieva, Galina A.
Format: Article
Language:English
Subjects:
Eschenmoser sulfide contraction
furazan
furoxan
glycoluril
thioglycoluril
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Summary:[Display omitted] 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.
ISSN:0959-9436
DOI:10.1016/j.mencom.2024.01.037