Dipyrazolodioxadiazocines as shelf-stable "ready-to-use" precursors for an in situ generation of enolate-iminium 1,4-dipoles: a straightforward atom-economical approach to pyrazolo[5,1-d][1,3,5]dioxazines

An original, facile and highly efficient method for the in situ generation of cyclic enolate-iminium 1,4-dipoles via unique thermal decomposition of easily available dipyrazolodioxadiazocines has been developed. Various substituted pyrazolo[5,1-d][1,3,5]dioxazines have been prepared in high yields v...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-05, Vol.18 (17), p.3382-3391
Main Authors: Zhulanov, Vladimir E, Vigovskaya, Valeria A, Dmitriev, Maksim V, Silaichev, Pavel S, Maslivets, Andrey N, Rubin, Michael
Format: Article
Language:English
Subjects:
Catalysts
Crystallography
Dipoles
Ketones
Thermal decomposition
X-ray crystallography
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Summary:An original, facile and highly efficient method for the in situ generation of cyclic enolate-iminium 1,4-dipoles via unique thermal decomposition of easily available dipyrazolodioxadiazocines has been developed. Various substituted pyrazolo[5,1-d][1,3,5]dioxazines have been prepared in high yields via unusual cycloconversion of dipyrazolodioxadiazocines in the presence of ketones. Furthermore, the developed method is 100% atom economical and proceeds under metal-, catalyst- and solvent-free conditions.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00451k