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Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles

Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles

We investigated the reactivity of various furans towards 2-azidobenzaldehydes, heterocyclic azidoaldehydes, and substituted 2-azidobenzyl alcohols to synthesize 2-(2-azidobenzyl)furan derivatives, revealing the azide group's remarkable compatibility with typical Friedel-Crafts reaction conditio...

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Հիմնական հեղինակներ: Abaev, V. T., Абаев, В. Т.
Ձևաչափ: Статья
Լեզու:English
Հրապարակվել է: John Wiley and Sons Inc 2024
Խորագրեր:
Azide
Furan
Dearomatization
Indole
Thermolysis
Առցանց հասանելիություն:https://dspace.ncfu.ru/handle/123456789/29511
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spelling ir-123456789-295112024-12-27T07:59:18Z Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles Abaev, V. T. Абаев, В. Т. Azide Furan Dearomatization Indole Thermolysis We investigated the reactivity of various furans towards 2-azidobenzaldehydes, heterocyclic azidoaldehydes, and substituted 2-azidobenzyl alcohols to synthesize 2-(2-azidobenzyl)furan derivatives, revealing the azide group's remarkable compatibility with typical Friedel-Crafts reaction conditions. Additionally, we demonstrated that these derivatives could be efficiently synthesized via a diazotization/azidation sequence from 2-(2-aminobenzyl)furans containing electron-donating substituents, successfully avoiding undesirable side reactions. Furthermore, we developed a synthetic methodology for preparing 2-(2-acylvinyl)indoles, involving the thermal generation of nitrenes to initiate furan ring opening. Notably, our approach utilizes the azidoaryl group and the furan ring separated by a saturated carbon atom that distinguishes it from known indole syntheses in which these moieties are conjugated. The broad applicability and high efficiency of our method, using readily available starting materials, highlight its potential as a versatile synthetic tool. 2024-12-27T07:57:43Z 2024-12-27T07:57:43Z 2024 Статья Chalikidi, P.N., Magkoev, T.T., Egorov, D.I., Kolodina, A.A., Uchuskin, M.G., Trushkov, I.V., Abaev, V.T. Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles // Asian Journal of Organic Chemistry. - 2024. - 13 (12). - статья № e202400373. - DOI: 10.1002/ajoc.202400373 https://dspace.ncfu.ru/handle/123456789/29511 en Asian Journal of Organic Chemistry application/pdf application/pdf John Wiley and Sons Inc
institution СКФУ
collection Репозиторий
language English
topic Azide
Furan
Dearomatization
Indole
Thermolysis
spellingShingle Azide
Furan
Dearomatization
Indole
Thermolysis
Abaev, V. T.
Абаев, В. Т.
Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
description We investigated the reactivity of various furans towards 2-azidobenzaldehydes, heterocyclic azidoaldehydes, and substituted 2-azidobenzyl alcohols to synthesize 2-(2-azidobenzyl)furan derivatives, revealing the azide group's remarkable compatibility with typical Friedel-Crafts reaction conditions. Additionally, we demonstrated that these derivatives could be efficiently synthesized via a diazotization/azidation sequence from 2-(2-aminobenzyl)furans containing electron-donating substituents, successfully avoiding undesirable side reactions. Furthermore, we developed a synthetic methodology for preparing 2-(2-acylvinyl)indoles, involving the thermal generation of nitrenes to initiate furan ring opening. Notably, our approach utilizes the azidoaryl group and the furan ring separated by a saturated carbon atom that distinguishes it from known indole syntheses in which these moieties are conjugated. The broad applicability and high efficiency of our method, using readily available starting materials, highlight its potential as a versatile synthetic tool.
format Статья
author Abaev, V. T.
Абаев, В. Т.
author_facet Abaev, V. T.
Абаев, В. Т.
author_sort Abaev, V. T.
title Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
title_short Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
title_full Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
title_fullStr Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
title_full_unstemmed Azide-Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
title_sort azide-induced furan ring opening for the synthesis of functionalized indoles
publisher John Wiley and Sons Inc
publishDate 2024
url https://dspace.ncfu.ru/handle/123456789/29511
work_keys_str_mv AT abaevvt azideinducedfuranringopeningforthesynthesisoffunctionalizedindoles
AT abaevvt azideinducedfuranringopeningforthesynthesisoffunctionalizedindoles
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