13159-83-6

Upstream product

• 123-30-8 4-amino-phenol 
• 104-88-1 4-chlorobenzaldehyde 
• 1749-05-9 4-{[(4-chlorophenyl)methylidene]amino}phenol 

Downstream Products

• 1613063-79-8 1-(4-chlorobenzyl)-2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitrile 
• 1613063-47-0 N-(4-chlorobenzyl)-2-cyano-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.