In Situ Generated TEMPO Oxoammonium Salt Mediated Tandem Cyclization of ß-Oxoamides with Amine Hydrochlorides for the Synthesis of Pyrrolin-4-ones.
J Org Chem
; 82(12): 6125-6132, 2017 06 16.
Article
em En
| MEDLINE
| ID: mdl-28516766
ABSTRACT
A novel in situ generated TEMPO oxoammonium salt mediated one-pot tandem reaction has been developed for the straightforward construction of pyrrolin-4-ones from readily available ß-oxoamides with amine hydrochlorides. The reaction tolerates various functional groups and represents a reliable method for the synthesis of highly substituted pyrrolin-4-ones in good yields under mild conditions. Detailed mechanistic studies disclosed that TEMPO oxoammonium salt generated in situ was crucial for the transformation involving the formation of enaminone precursors in situ by condensation of the ß-oxoamides with amines, followed by sequential oxidative coupling with ß-oxoamides, intramolecular cyclization, and 1,2-alkyl migration steps.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2017
Tipo de documento:
Article