ortho-Amidoalkylation of Phenols via Tandem One-Pot Approach Involving Oxazine Intermediate

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• 作者：Ramesh Mudududdla ; Shreyans K. Jain ; Jaideep B. Bharate ; Ajai P. Gupta ; Baldev Singh ; Ram A. Vishwakarma ; Sandip B. Bharate
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：October 5, 2012
• 年：2012
• 卷：77
• 期：19
• 页码：8821-8827
• 全文大小：427K
• 年卷期：v.77,no.19(October 5, 2012)
• ISSN：1520-6904

文摘

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鈥揂lder cycloaddition and acid catalyzed oxazine ring-opening.