1613063-57-2

Upstream product

• 129121-76-2 4-{[(4-nitrophenyl)methylene]amino}phenol 
• 555-16-8 4-nitrobenzaldehdye 
• 123-30-8 4-amino-phenol 
• 803621-35-4 4-(4-Nitro-benzylamino)-phenol 
• 372-09-8 cyanoacetic acid 

Downstream Products

• 1613063-89-0 1-(4-nitrobenzyl)-2,7-dioxo-1-azaspiro[3.5]nona-5,8-diene-3-carbonitrile 

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.