title: ortho-Amidoalkylation of phenols via tandem one-pot approach involving oxazine intermediate.
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.
authors.affiliation: Medicinal Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu-180001, India.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Mudududdla
authors.forename: Shreyans K
authors.initials: SK
authors.lastname: Jain
authors.forename: Jaideep B
authors.initials: JB
authors.lastname: Bharate
authors.forename: Ajai P
authors.initials: AP
authors.lastname: Gupta
authors.forename: Baldev
authors.initials: B
authors.lastname: Singh
authors.forename: Ram A
authors.initials: RA
authors.lastname: Vishwakarma
authors.forename: Sandip B
authors.initials: SB
authors.lastname: Bharate
mesh_terms: D000478:Alkylation; D003500:Cyclization; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*
chemical_list: D010078:Oxazines; D010636:Phenols