Tailored Aza‐Michael Addition as Key Step in the Synthesis of 1H‐imidazooxazine Scaffolds

Tailored Aza‐Michael Addition as Key Step in the Synthesis of 1H‐imidazooxazine Scaffolds

A novel protocol for the efficient synthesis of 1H‐imidazo[5,1‐c][1,4]oxazines has been developed. Aza‐Michael addition of selected primary amines to 1,2‐diaza‐1,3‐dienes (DDs) combined with isothiocyanates or isocyanates in sequential 3‐CR process, affords 2‐thiohydantoins and hydantoins with suita...

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Veröffentlicht in:European journal of organic chemistry 2022-10, Vol.2022 (40)
Hauptverfasser: Mari, Giacomo, De Crescentini, Lucia, Favi, Gianfranco, Mantellini, Fabio, Santeusanio, Stefania
Format: Artikel
Sprache:eng
Schlagworte:
Amines
Dienes
Functional groups
Hydantoin
Isocyanates
Synthesis
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Zusammenfassung:A novel protocol for the efficient synthesis of 1H‐imidazo[5,1‐c][1,4]oxazines has been developed. Aza‐Michael addition of selected primary amines to 1,2‐diaza‐1,3‐dienes (DDs) combined with isothiocyanates or isocyanates in sequential 3‐CR process, affords 2‐thiohydantoins and hydantoins with suitably positioned functional groups to be used for chemoselective acid‐promoted ring‐fused formation.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202201053