New Alkaloid Derivatives by the Reaction of 3,4-Dihydro-β-Carbolines with 1,3- Dipoles; Synthesis and a Theoretical Study[1]

Title: New Alkaloid Derivatives by the Reaction of 3,4-Dihydro-β-Carbolines with 1,3- Dipoles; Synthesis and a Theoretical Study[1]

Volume: 15 Issue: 11

Author(s): Matyas Milen, Peter Abranyi-Balogh, Zoltan Mucsi, Andras Dancso, Tamas Kortvelyesi and Gyorgy Keglevich

Affiliation:

Keywords: β-carbolines, cycloaddition, nitrile oxide, nitrile imine, mechanism, oxadiazolo-pyridoindole derivatives, Stereostructure, harmala alkaloids, hallucinogenic, brain GABA receptors, Pictet-Spengler reaction, liver-diseases, Tuboflavine, isotuboflavine, norisotuboflavine

Abstract: The reaction of 3,4-dihydro-β-carboline derivatives with 1,3-dipoles, such as a nitrile imine and a nitrile oxide led to triazolopyridoindole and oxadiazolo-pyridoindole derivatives, respectively, that are novel synthetic alkaloids. Stereostructure, stability and further reactions of the pyridoindoles were also investigated. The oxadiazolo-pyridoindoles underwent reaction with a second unit of nitrile oxide to afford the corresponding trisubstituted 1,2,4-triazole 2-oxides. The mechanisms of the above reactions were studied in detail by high level quantum chemical calculations. It was found that the reaction of the 1,3-dipoles is not an expected 1,3-cycloaddition, but rather a stepwise addition reaction. The exact mechanism was found to be dependent on the substitution pattern.

Cite this article as:

Milen Matyas, Abranyi-Balogh Peter, Mucsi Zoltan, Dancso Andras, Kortvelyesi Tamas and Keglevich Gyorgy, New Alkaloid Derivatives by the Reaction of 3,4-Dihydro-β-Carbolines with 1,3- Dipoles; Synthesis and a Theoretical Study[1], Current Organic Chemistry 2011; 15 (11) . https://dx.doi.org/10.2174/138527211795656660