1208104-83-9Relevant academic research and scientific papers
Ruthenium Catalyzed Tandem Pictet-Spengler Reaction
Cherepakhin, Valeriy,Nalikezhathu, Anju,Williams, Travis J.
, (2020)
We report a pyridyl-phosphine ruthenium(II) catalyzed tandem alcohol amination/Pictet-Spengler reaction sequence to synthesize tetrahydro-β-carbolines from an alcohol and tryptamine. Our conditions use a Lewis acid cocatalyst, In(OTf)3, that is compatible with typically base catalyzed amination and an acid catalyzed Pictet-Spengler cyclization. This method proceeds well with benzylic alcohols, heterocyclic carbinols, and aliphatic alcohols. We also show how combining this reaction with a subsequent cycloamination enables a direct synthesis of tetracyclic alkaloids like harmicine.
Novel synthesis of tetrahydro-β-carbolines and tetrahydroisoquinolines via three-component reaction using hexagonally ordered mesoporous AlSBA-15 catalysts
Vinu, Ajayan,Kalita, Pranjal,Samie, Leila,Chari, Murugulla Adharvana,Pal, Ravindra,Reddy, B.V. Subba
experimental part, p. 702 - 706 (2010/04/02)
Tryptamine, aryl aldehyde, and benzyl chloride undergo smooth coupling using well-ordered mesoporous AlSBA-15 catalyst with hexagonal porous structure in acetonitrile at 80 °C to furnish tetrahydrocarbolines in good yields with a high selectivity. This reaction also proceeds with homoveratrylamine to give the corresponding tetrahydroisoquinolines. A variety of aryl and heteroaryl aldehydes have also been used for producing tetrahydrocarbolines in high yields. This AlSBA-15-promoted Pictet-Spengler reaction provides a mild alternative to the traditional Bro?nsted or Lewis acids typically employed for the preparation of tetrahydrocarbolines and tetrahydroisoquinolines. Crown Copyright
