1379771-50-2

Upstream product

• 103-80-0 phenylacetyl chloride 
• 243844-35-1 N-[2-(chloromethyl)-phenyl]-4-methylbenzene-1-sulfonamide 
• 129423-29-6 [(1E)-3-phenylprop-1-en-1-yl]boronic acid 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 497236-62-1 N-(2-ethynylphenyl)-4-toluenesulfonamide 
• 78725-72-1 α-ethynyl-2-nitrophenylmethanol 
• 552-89-6 2-nitro-benzaldehyde 
• 1379771-04-6 C₉H₉NO 
• 1315477-55-4 N-[2-(1-hydroxyprop-2-yn-1-yl)phenyl]-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Tandem Phospha-Michael Addition/N-Acylation/ Intramolecular Wittig Reaction of aza-o-Quinone Methides: Approaches to 2,3-Disubstituted Indoles

A tandem phospha-Michael addition/N-acylation/intramolecular Wittig reaction of in situ formed aza-o-QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions. (Figure presented.).

2-substituted indole compound and preparation method thereof

The invention provides a 2-substituted indole compound. The compound is of a structure shown as a formula I, wherein R1 is selected from hydrogen, alkoxy, hydroxyl and halogen, and the position and the number of R1 cannot be fixed; R2 is selected from hydrogen, alkyl and C6 aryl; R3 is selected from a C6 aryl group, a C4-C8 heteroaryl group, a C1-C7 alkyl group, a C1-C6 cycloalkyl group, a C8 alkenyl group, a C4 ester group, and a trifluoromethyl group, and the C6 aryl group may have optionally one or more substitutions independently selected from the group consisting of hydrogen, C1 alkoxy, and halogen. The preparation method comprises the following steps: adding a compound shown as a formula A, a solvent, triphenylphosphine, an alkali and a compound shown as a formula B into a reaction flask at room temperature; putting the reaction system in the step (1) into an oil bath pan, uniformly stirring and reacting, and detecting a reaction endpoint by TLC; and taking out the reaction system in the step (2), separating and purifying to obtain the target compound shown in the formula I. The preparation method provided by the invention can be used for efficiently and quickly preparing the2-substituted indole compound.

Selenium-catalyzed oxidative c(sp2)-h amination of alkenes exemplified in the expedient synthesis of (Aza-)indoles

A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp2)-N bonds in high yields and with excellent functional group tolerance.

Benzofuran and indole synthesis via Cu(i)-catalyzed coupling of N-tosylhydrazone and o-hydroxy or o-amino phenylacetylene

A general and practical method to synthesize 2-substituted benzofurans and indoles is described. This method employs easily accessible N-tosylhydrazones and o-hydroxy or o-amino phenylacetylenes as substrates. The reaction proceeds through a CuBr-catalyzed coupling-allenylation-cyclization sequence under ligand-free conditions.

Palladium-catalyzed approach for the general synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/ nosyltetrahydroquinolines: Access to 2-substituted indoles and quinolines

A facile and efficient method for the synthesis of (E)-2-arylmethylidene-N- tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinoline variants has been developed through palladium-catalyzed cyclocondensation of aryl iodides with readily available 1-(2-tosylaminophenyl)prop-2-yn-1-ols and their higher homologues, respectively. The proposed reaction mechanism invokes the operation of trans-aminopalladation during cyclization (5/6-exo-dig), which ensures exclusive (E)-stereochemistry in the products. The method is fast, operationally simple, totally regio- and stereoselective, and versatile enough to access a variety of 2-substituted indoles and quinolines. The reactions proceeded efficiently with a wide variety of substrates and afforded the corresponding products in moderate to excellent yields.