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Title: Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
Authors: Aksenov, N. A.
Аксенов, Н. А.
Arutiunov, N. A.
Арутюнов, Н. А.
Aksenov, A. V.
Аксенов, А. В.
Kirilov, N. K.
Кирилов, Н. К.
Aksenova, I. V.
Аксенова, И. В.
Aksenov, D. A.
Аксенов, Д. А.
Aleksandrova, E. V.
Александрова, Е. В.
Rubin, M. A.
Рубин, М. А.
Keywords: Beta-carboline;Indole;Electrocyclization;Harmane;Heterocycle;Norharmane
Issue Date: 2023
Citation: Aksenov, N.A., Arutiunov, N.A., Aksenov, A.V., Kirilov, N.K., Aksenova, I.V., Aksenov, D.A., Aleksandrova, E.V., Rubin, M., Kornienko, A. Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles // International Journal of Molecular Sciences. - 2023. - 24 (17), статья № 13107. - DOI: 10.3390/ijms241713107
Series/Report no.: International Journal of Molecular Sciences
Abstract: The β-carboline motif is common in drug discovery and among numerous biologically active natural products. However, its synthetic preparation relies on multistep sequences and heavily depends on the type of substitution required in the core of the desired β-carboline target. Herein, we demonstrate that this structural motif can be accessed with the microwave-assisted electrocyclic cyclization of heterotrienic aci (alkylideneazinic acid) forms of 3-nitrovinylindoles. The reaction can start with 3-nitrovinylindoles themselves under two sets of conditions. The first one involves microwave irradiation of butanolic solutions of 3-nitrovinylindoles, whereas the second one consists of prior Boc protection of indolic nitrogen, where the protecting group cleanly comes off during the course of the reaction. Alternatively, the reaction can start with 3-nitrovinylindoles prepared in situ using various processes. Finally, the reaction may utilize indoles with β-nitrostyrenes, likely involving the intermediacy of spirocyclic oxazolines, which rearrange to similar heterotrienic systems undergoing cyclization to β-carbolines. As part of this study, several natural products, namely, alkaloids norharmane, harmane, and eudistomin N, were synthesized.
Appears in Collections:Статьи, проиндексированные в SCOPUS, WOS

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