13174-40-8

Upstream product

• 13160-77-5 4-hydroxy-N-(3,4-dimethoxyaminobenzylidene)aniline 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 123-30-8 4-amino-phenol 

Downstream Products

• 1169411-35-1 ethyl 3-((3,4-dimethoxybenzyl)(4-hydroxyphenyl)amino)-3-oxopropanoate 
• 1613063-75-4 1-(3,4-Dimethoxybenzyl)-2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitrile 
• 1613063-43-6 2-cyano-N-(3,4-dimethoxybenzyl)-N-(4-hydroxyphenyl)acetamide 

Relevant academic research and scientific papers

Versatile synthesis of 4-spiro-β-lactam-3-carbonitriles via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides

A series of 4-spiro-cyclohexadienonyl-β-lactam-3-carbonitriles, 2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitriles, was synthesized in satisfactory to excellent yields via the intramolecular nucleophilic cyclization of N-(p-hydroxyphenyl)cyanoacetamides with iodobenzene diacetate (IBD) as oxidant and potassium hydroxide as base. Acetic 4-spiro-cyclohexadienonyl- β-lactam-3-carbimidic anhydrides were obtained when organic base triethylamine was applied instead of potassium hydroxide. The mechanisms of the intramolecular nucleophilic cyclization and formation of acetic β-lactam-3-carbimidic anhydrides were proposed. The cyclization is a sequence of nucleophilic ipso addition and oxidative dearomatization. The formation of acetic carbimidic anhydrides is an acid-catalyzed acetate addition to the nitriles.