1383663-46-4

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 10075-50-0 5-bromo-1H-indole 
• 19816-85-4 N'-(1,2-diphenylethylidene)-4-methylbenzenesulfonohydrazide 
• 536-74-3 phenylacetylene 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 1383663-79-3 (Z)-1-(1,2-diphenylvinyl)-5-(thiophen-3-ylethynyl)-1H-indole 
• 1383663-77-1 (Z)-5-(2,5-dimethoxyphenyl)-1-(1,2-diphenylvinyl)-1H-indole 
• 1383663-78-2 (E)-methyl 3-(1-((Z)-1,2-diphenylvinyl)-1H-indol-5-yl)acrylate 
• 1620817-25-5 (Z)-1-(1,2-diphenylvinyl)-N-(pyridin-3-yl)-1H-indol-5-amine 

Relevant academic research and scientific papers

Tandem one-pot palladium-catalyzed coupling of hydrazones, haloindoles, and amines: Synthesis of amino-N-vinylindoles and their effect on human colon carcinoma cells

The synthesis of amino-substituted N-vinylazoles was achieved by a new palladium-assisted tandem catalytic reaction involving N-tosylhydrazones, halo-substituted azoles, and amines. Accordingly, two Csp2-N bonds were formed through two mechanistically distinct reactions using a single PdII/Pd0 catalyst system in a one-pot fashion. This work paves the way for the design of biological relevant compounds in an amino-substituted N-vinylindole series. Among several polyoxygenated derivatives evaluated, compounds 5e and 5u were found to exhibit good antiproliferative activity.

Base-mediated selective synthesis of diversely substituted N-heterocyclic enamines and enaminones by the hydroamination of alkynes

Regio- and stereoselective alkynylation of various N-heterocycles 1a-l using potassium and cesium salts in DMSO is described. Terminal alkynes 2a-k and internal alkynes 4a-f provided the kinetically stable Z-enamines 3a-l and 5a-i in good to excellent yields using KOH at 120 °C. Addition of heterocyclic amines to 1,3- and 1,4-diethynylbenzene 6a-b provided the mixture of E/Z isomers with KOH; however, with Cs2CO3 selectively Z-isomers 7ab-db were obtained by the hydroamination at one triple bond. This developed methodology also provides an easy and novel access for the synthesis of enaminones 10a-c. The detailed work also supports the formation of cis-isomer by preferential addition of o-haloarylalkynes followed by intramolecular C2 arylation in the copper-catalyzed tandem synthesis of indolo and pyrrolo[2,1-a]isoquinolines.