Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles

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 t...

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Autori principali:	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.
Natura:	Статья
Lingua:	English
Pubblicazione:	2023
Soggetti:	Beta-carboline Indole Electrocyclization Harmane Heterocycle Norharmane
Accesso online:	https://dspace.ncfu.ru/handle/20.500.12258/25549
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spelling	ir-20.500.12258-255492023-09-26T10:05:46Z Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles 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. Beta-carboline Indole Electrocyclization Harmane Heterocycle Norharmane 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. 2023-09-26T10:04:02Z 2023-09-26T10:04:02Z 2023 Статья 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 http://hdl.handle.net/20.500.12258/25549 en International Journal of Molecular Sciences application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	Beta-carboline Indole Electrocyclization Harmane Heterocycle Norharmane
spellingShingle	Beta-carboline Indole Electrocyclization Harmane Heterocycle Norharmane 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. Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
description	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.
format	Статья
author	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.
author_facet	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.
author_sort	Aksenov, N. A.
title	Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
title_short	Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
title_full	Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
title_fullStr	Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
title_full_unstemmed	Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles
title_sort	synthesis of β-carbolines with electrocyclic cyclization of 3-nitrovinylindoles
publishDate	2023
url	https://dspace.ncfu.ru/handle/20.500.12258/25549
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Synthesis of β-Carbolines with Electrocyclic Cyclization of 3-Nitrovinylindoles

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