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.
Tailored Aza-Michael Addition as Key Feature of Novel Approach to 1H-imidazo[5,1-c][1,4]oxazine Scaffolds
Giacomo Mari
;Lucia De Crescentini;Gianfranco Favi;Fabio Mantellini;Stefania Santeusanio
2022
Abstract
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.File in questo prodotto:
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Eur J Org Chem - 2022 - Mari - Tailored Aza‐Michael Addition as Key Step in the Synthesis of 1H‐imidazo 5 1‐c 1 4 oxazine.pdf
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