220462-67-9

Upstream product

• 132593-60-3 3-benzyl-4-hydroxy-5,8-dimethyl-1H-quinolin-2-one 
• 220462-64-6 bromo-acetic acid 3-benzyl-5,8-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-quinolin-3-yl ester 
• 220462-70-4 3-benzyl-3-hydroxy-5,8-dimethyl-1,2,3,4-tetrahydroquinoline-2,4-dione 
• 607-81-8 diethyl 2-benzylmalonate 
• 95-78-3 2,5-Dimethylaniline 

Downstream Products

• 220462-55-5 3a-benzyl-6,9-dimethyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinoline-2,4-dione 

Relevant academic research and scientific papers

Unprecedented reactivity of 5-substituted 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones with ethyl (triphenylphosphoranylidene)acetate

3,5,8-Trisubstituted 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones (3) reacted with ethyl (triphenylphosphoranylidene)acetate (4) to yield several products. The major products, 4,7-disubstituted 1,3-dihydro-3-phenylacetoxy-2H-indol-2-ones (5) and (11), were formed via the molecular rearrangement of 3, catalyzed by the strongly basic Wittig reagent. The Wittig reaction at the lactam group of 3, resulting in 2-ethoxycarbonylmethylene derivatives, can be explained by the poor reactivity of the sterically hindered 4-oxo group. Under acid catalysis, the Wittig reaction proceeded at the hindered 4-oxo group as well. A series of minor products were also obtained through the Wittig reaction of 3. A reaction mechanism of the molecular rearrangement of substances (3) is proposed.