220462-69-1

Upstream product

• 220462-68-0 3-benzyl-5-chloro-4-hydroxy-8-methyl-1H-quinolin-2-one 
• 607-81-8 diethyl 2-benzylmalonate 
• 95-79-4 5-chloro-2-methyl-benzenamine 

Downstream Products

• 220462-63-5 bromo-acetic acid 3-benzyl-5-chloro-8-methyl-2,4-dioxo-1,2,3,4-tetrahydro-quinolin-3-yl ester 
• 220462-51-1 3a-benzyl-9-chloro-6-methyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinoline-2,4-dione 
• 61258-72-8 4-Chloro-7-methyl-1H-indole-2,3-dione 
• 220462-47-5 4-chloro-1,3-dihydro-7-methyl-3-phenylacetoxy-2H-indol-2-one 

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.