Challenge N- versus O-six-membered annulation: FeCl3-catalyzed synthesis of heterocyclic N,O-aminals

Challenge N- versus O-six-membered annulation: FeCl3-catalyzed synthesis of heterocyclic N,O-aminals

A new class of heterocyclic N,O-aminal and hemiaminal scaffolds was successfully obtained by means of a three-component reaction (3-CR) of 1,2-diaza-1,3-dienes (DDs), α-aminoacetals and iso(thio)cyanates. These stable imine surrogates are generated from key-substituted (thio)hydantoin intermediates...

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Veröffentlicht in:Beilstein journal of organic chemistry 2024-06, Vol.20 (1), p.1412-1420
Hauptverfasser: Mari, Giacomo, De Crescentini, Lucia, Favi, Gianfranco, Mantellini, Fabio, Olivieri, Diego, Santeusanio, Stefania
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Full Research Paper
fused-ring systems
heterocyclic hemiaminals
heterocyclic n,o-aminals
multicomponent reactions
α-aminoacetals
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Zusammenfassung:A new class of heterocyclic N,O-aminal and hemiaminal scaffolds was successfully obtained by means of a three-component reaction (3-CR) of 1,2-diaza-1,3-dienes (DDs), α-aminoacetals and iso(thio)cyanates. These stable imine surrogates are generated from key-substituted (thio)hydantoin intermediates through selective FeCl3-catalyzed intramolecular N-annulation.A new class of heterocyclic N,O-aminal and hemiaminal scaffolds was successfully obtained by means of a three-component reaction (3-CR) of 1,2-diaza-1,3-dienes (DDs), α-aminoacetals and iso(thio)cyanates. These stable imine surrogates are generated from key-substituted (thio)hydantoin intermediates through selective FeCl3-catalyzed intramolecular N-annulation.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.20.123