132653-75-9

Upstream product

• 2297-94-1 5-nitrosotropolone 
• 62-53-3 aniline 
• 132653-70-4 5-Hydroxy-8-p-tolyl-8-aza-bicyclo[3.2.1]oct-3-ene-2,6-dione 2-oxime 
• 132653-71-5 5-Hydroxy-8-phenyl-8-aza-bicyclo[3.2.1]oct-3-ene-2,6-dione 2-oxime 

Downstream Products

• 99-50-3 3,4-Dihydroxybenzoic acid 
• 132653-83-9 1-Hydroxy-6-phenyl-6-aza-bicyclo[3.2.1]octane-4,7-dione 
• 132653-79-3 1-Hydroxy-6-phenyl-6-aza-bicyclo[3.2.1]oct-2-ene-4,7-dione 

Relevant academic research and scientific papers

Structure of Reaction Products of 5-Nitrosotropolone and Arylamine

The structures of abnormal reaction products (1:1 and 1:2) between 5-nitrosotropolone and arylamine are elucidated.The reaction of 5-nitrosotropolone with arylamine (e.g., aniline and p-toluidine) affords initially a bicyclic addition product, having 8-azabicyclooctane system which could be formed by the attack of the amine on 4- and 1-positions of the tropolone ring.The adduct contains two isomers having syn and anti configuration with respect to the hydroxyimino group.These adducts easily isomerized under alkaline conditions to form lactams having the 6-azabicyclo octane system, which may have been resulted from skeletal rearrangement of a seven-membered ring to a six-membered one.The former adducts, the 8-azabicyclooctane system, further react with another mole of arylamine to give 1:2 products containing a lactam moiety via similar skeletal rearrangement.