New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons

New tetracyclic 1,4-oxazepines constructed via practically simple tandem condensation strategy from readily available synthons

A streamlined synthetic methodology towards novel tetracyclic 1,4-oxazepines from readily available precursors is described. The compounds, designed as more soluble version of the earlier described, poorly soluble dibenzo[b,f][1,4]oxazepines, were obtained in high yields and as a single regioisomer...

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Veröffentlicht in:Tetrahedron 2014-02, Vol.70 (5), p.1077-1083
Hauptverfasser: Sapegin, Alexander V., Kalinin, Stanislav A., Smirnov, Alexey V., Dorogov, Mikhail V., Krasavin, Mikhail
Format: Artikel
Sprache:eng
Schlagworte:
Aromatic compounds
Bioisosteres
Condensing
Construction
Denitrocyclization
Methodology
Nucleophilic aromatic substitution
Oxazepines
Precursors
Privileged structures
Smiles rearrangement
Solubilizing groups
Strategy
Tetracyclic
Tetrahedrons
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Zusammenfassung:A streamlined synthetic methodology towards novel tetracyclic 1,4-oxazepines from readily available precursors is described. The compounds, designed as more soluble version of the earlier described, poorly soluble dibenzo[b,f][1,4]oxazepines, were obtained in high yields and as a single regioisomer as a result of three tandem chemical events—nucleophilic aromatic substitution, Smiles rearrangement and denitrocyclization. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.12.026