ortho-Amidoalkylation of phenols via tandem one-pot approach involving oxazine intermediate.
J Org Chem
; 77(19): 8821-7, 2012 Oct 05.
Article
em En
| MEDLINE
| ID: mdl-22970791
ABSTRACT
A new and efficient method for ortho-amidoalkylation of phenols via Mannich-type condensation with formaldehyde and lactams using recyclable solid acid catalyst is described. This is the first report for ortho-amidoalkylation of phenols by lactams via Mannich-type condensation. LC-ESI-MS/MS based mechanistic study revealed that reaction proceeds through o-quinone methide (o-QM) and an oxazine intermediate via tandem Knoevenagel condensation, formal [4 + 2]-Diels-Alder cycloaddition and acid catalyzed oxazine ring-opening.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Oxazinas
/
Fenóis
Idioma:
En
Ano de publicação:
2012
Tipo de documento:
Article