Ortho-amidoalkylation of phenols via tandem one-pot approach involving oxazine intermediate

Ramesh Mudududdla, Shreyans K. Jain, Jaideep B. Bharate, Ajai P. Gupta, Baldev Singh, Ram A. Vishwakarma, Sandip B. Bharate

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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.

Original languageEnglish
Pages (from-to)8821-8827
Number of pages7
JournalJournal of Organic Chemistry
Issue number19
Publication statusPublished - 5 Oct 2012
Externally publishedYes

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