Reaction of 3,4-Dihydro-β-Carbolines with 4-Fluorophenyl-Nitrile Oxide

Title: Reaction of 3,4-Dihydro-β-Carbolines with 4-Fluorophenyl-Nitrile Oxide

Volume: 7 Issue: 5

Author(s): Matyas Milen, Peter Abranyi-Balogh, Andras Dancso, Gyula Simig and Gyorgy Keglevich

Affiliation:

Keywords: Alkaloides, 3,4-dihydro-β-carboline, nitrile oxide, cycloaddition, oxadiazolo-pyrido-indole

Abstract: The reaction of 3,4-dihydro-β-carboline 5a with the nitrile oxide generated from 4-fluoro-N-hydroxybenzenecarboximidoyl chloride (6) gave novel adduct 7a that on standing at 26 °C in CDCl3 was isomerized to species 8. As an extension, the reaction of the dihydro-β-carbolines substituted on C(1) (5b-e) afforded the analogous adducts (7b-e). In case of using two equivalents of reagent 6, the corresponding 1,2,4-triazole-2-oxide (10b-e) was also formed beside the adduct (7b-e).

Cite this article as:

Milen Matyas, Abranyi-Balogh Peter, Dancso Andras, Simig Gyula and Keglevich Gyorgy, Reaction of 3,4-Dihydro-β-Carbolines with 4-Fluorophenyl-Nitrile Oxide, Letters in Organic Chemistry 2010; 7 (5) . https://dx.doi.org/10.2174/157017810791514913