169263-30-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 37585-25-4 2-amino-5-chlorobenzyl alcohol 
• 675578-47-9 N-(4-chloro-2-(hydroxymethyl)phenyl)-4-methylbenzenesulfonamide 
• 34159-03-0 N-(4-chloro-2-formylphenyl)-4-methylbenzenesulfonamide 
• 100-58-3 phenylmagnesium bromide 
• 719-64-2 5-chloro-3-phenylanthranil 
• 719-59-5 5-chloro-2-aminobenzophenone 
• 4873-59-0 2-tosylamido-5-chlorobenzophenone 
• 591-51-5 phenyllithium 
• 1159372-20-9 (2-amino-5-chlorophenyl)(phenyl)methanol 

Downstream Products

• 36004-55-4 (5-chloro-3-phenyl-1H-indol-2-yl)(phenyl)methanone 
• 1402043-16-6 N-(2-(chloro(phenyl)methyl)-4-chlorophenyl)-4-methylbenzenesulfonamide 
• 924635-58-5 4-[5-chloro-1-(4-methylphenylsulfonyl)-3-phenyl-1H-2-indolyl]-2-butanone 
• 924635-56-3 4-methyl-N-{4-chloro-2-[(5-methylfuran-2-yl)(phenyl)methyl]phenyl}benzenesulfonamide 
• 4873-59-0 2-tosylamido-5-chlorobenzophenone 
• 182145-46-6 6-Chloro-N-(4-methylphenylsulfonyl)-4-phenyl-1,4-dihydro-2H-3,1-benzoxazin-2-one 

Relevant academic research and scientific papers

Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles

A novel strategy based on Cu-catalyzed (4+1) cascade annulation of terminal alkynes as one-carbon synthons with 2-(tosylmethyl)anilines has been developed for the expeditious synthesis of 2,3-disubstituted indoles, in which in situ generations of aza-o-quinone methides and alkynyl-copper(I) species are involved. This annulation provides an effective method for the assembly of synthetically and structurally interesting 2,3-disubstituted indoles.

Simple route to 3-(2-indolyl)-1-propanones via a furan recyclization reaction

A simple route to 1-R-3-(2-indolyl)-1-propanones has been elaborated based on recyclization of 2-(2-aminobenzyl)furan derivatives. Being a modification of the Reissert indole synthesis, our approach employs the furan ring as a source of carbonyl function. This approach is general and allows varying of substituents in aromatic ring as well as in 3-position of indole nucleus.

New synthesis of 3-substituted indoles using lithium trimethylsilyldiazomethane

Lithium trimethylsilyldiazomethane smoothly reacted with N-tosyl-o-acylanilines to give 3-substituted indoles in good to high yields.

Diels-Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives

N-Tosyl- and N-alkylidene-sulfonyl substituted 1,4-dihydro-2A-3,1-benzoxazin-2-ones 2c-g easily undergo thermal carbon dioxide extrusion leading to the aza-ortho-xylylenes 3c-g. The intermediates 3c,d can be trapped by electron-poor ethylenic and acetylenic dienophiles, giving tetrahydroquinoline and quinoline derivatives. The reactions of 2c with non-symmetrical dienophiles are completely regioselective. N-Alkylidenesulfonyl substituted aza-orthro-xylylenes 3f-g undergo intramolecular Diels-Alder reactions leading to the tricyclic compounds 10 and 11, while the aza-ortho-xylylene generated from 4-(hex-5-enyl)-N-(4-methylphenylsulfonyl)-1,4-tetrahydro-2H-3,1-benzoxazin-2-one undergoes a [1,5] hydrogen shift leading to N-[2-(1E)-hepta-1,6-dien-1-ylphenyl]-4-methylbenzenesulfonamide.