Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines

A new variant of Fisher indole synthesis involving Bronsted acid-catalyzed hydrohydrazination of unactivated terminal and internal acetylenes with arylhydrazines is reported. The use of polyphosphoric acid alone either as the reaction medium or in the presence of a co-solvent appears to provide the...

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Главные авторы:	Aksenov, A. V., Аксенов, А. В., Makieva, D. C., Макиева, Д. С., Arestov, R. A., Арестов, Р. А., Arutiunov, N. A., Арутюнов, Н. А., Aksenov, D. A., Аксенов, Д. А., Aksenov, N. A., Аксенов, Н. А., Leontiev, A. V., Леонтьев, А. В., Aksenova, I. V., Аксенова, И. В.
Format:	Статья
Jezik:	English
Izdano:	Multidisciplinary Digital Publishing Institute (MDPI) 2024
Teme:	Alkyne hydrolysis Fisher indoles Alkynes hydroamination Cascade transformations Arylhydrazines Cyclization Metal-free
Online dostop:	https://dspace.ncfu.ru/handle/123456789/29159
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id	ir-123456789-29159
record_format	dspace
spelling	ir-123456789-291592024-10-18T11:16:12Z Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines Aksenov, A. V. Аксенов, А. В. Makieva, D. C. Макиева, Д. С. Arestov, R. A. Арестов, Р. А. Arutiunov, N. A. Арутюнов, Н. А. Aksenov, D. A. Аксенов, Д. А. Aksenov, N. A. Аксенов, Н. А. Leontiev, A. V. Леонтьев, А. В. Aksenova, I. V. Аксенова, И. В. Alkyne hydrolysis Fisher indoles Alkynes hydroamination Cascade transformations Arylhydrazines Cyclization Metal-free A new variant of Fisher indole synthesis involving Bronsted acid-catalyzed hydrohydrazination of unactivated terminal and internal acetylenes with arylhydrazines is reported. The use of polyphosphoric acid alone either as the reaction medium or in the presence of a co-solvent appears to provide the required balance for activating the C–C triple bond towards the nucleophilic attack of the hydrazine moiety without unrepairable reactivity loss of the latter due to competing amino group protonation. Additionally, the formal hydration of acetylenes to the corresponding ketones occurs under the same conditions, making it an alternative approach for generating carbonyl groups from alkynes. 2024-10-18T11:13:29Z 2024-10-18T11:13:29Z 2024 Статья Aksenov, A.V., Makieva, D.C., Arestov, R.A., Arutiunov, N.A., Aksenov, D.A., Aksenov, N.A., Leontiev, A.V., Aksenova, I.V. Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines // International Journal of Molecular Sciences. - 2024. - 25 (16). - статья № 8750. - DOI: 10.3390/ijms25168750 https://dspace.ncfu.ru/handle/123456789/29159 en International Journal of Molecular Sciences application/pdf application/pdf Multidisciplinary Digital Publishing Institute (MDPI)
institution	СКФУ
collection	Репозиторий
language	English
topic	Alkyne hydrolysis Fisher indoles Alkynes hydroamination Cascade transformations Arylhydrazines Cyclization Metal-free
spellingShingle	Alkyne hydrolysis Fisher indoles Alkynes hydroamination Cascade transformations Arylhydrazines Cyclization Metal-free Aksenov, A. V. Аксенов, А. В. Makieva, D. C. Макиева, Д. С. Arestov, R. A. Арестов, Р. А. Arutiunov, N. A. Арутюнов, Н. А. Aksenov, D. A. Аксенов, Д. А. Aksenov, N. A. Аксенов, Н. А. Leontiev, A. V. Леонтьев, А. В. Aksenova, I. V. Аксенова, И. В. Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines
description	A new variant of Fisher indole synthesis involving Bronsted acid-catalyzed hydrohydrazination of unactivated terminal and internal acetylenes with arylhydrazines is reported. The use of polyphosphoric acid alone either as the reaction medium or in the presence of a co-solvent appears to provide the required balance for activating the C–C triple bond towards the nucleophilic attack of the hydrazine moiety without unrepairable reactivity loss of the latter due to competing amino group protonation. Additionally, the formal hydration of acetylenes to the corresponding ketones occurs under the same conditions, making it an alternative approach for generating carbonyl groups from alkynes.
format	Статья
author	Aksenov, A. V. Аксенов, А. В. Makieva, D. C. Макиева, Д. С. Arestov, R. A. Арестов, Р. А. Arutiunov, N. A. Арутюнов, Н. А. Aksenov, D. A. Аксенов, Д. А. Aksenov, N. A. Аксенов, Н. А. Leontiev, A. V. Леонтьев, А. В. Aksenova, I. V. Аксенова, И. В.
author_facet	Aksenov, A. V. Аксенов, А. В. Makieva, D. C. Макиева, Д. С. Arestov, R. A. Арестов, Р. А. Arutiunov, N. A. Арутюнов, Н. А. Aksenov, D. A. Аксенов, Д. А. Aksenov, N. A. Аксенов, Н. А. Leontiev, A. V. Леонтьев, А. В. Aksenova, I. V. Аксенова, И. В.
author_sort	Aksenov, A. V.
title	Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines
title_short	Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines
title_full	Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines
title_fullStr	Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines
title_full_unstemmed	Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines
title_sort	metal-free, ppa-mediated fisher indole synthesis via tandem hydroamination–cyclization reaction between simple alkynes and arylhydrazines
publisher	Multidisciplinary Digital Publishing Institute (MDPI)
publishDate	2024
url	https://dspace.ncfu.ru/handle/123456789/29159
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Metal-Free, PPA-Mediated Fisher Indole Synthesis via Tandem Hydroamination–Cyclization Reaction between Simple Alkynes and Arylhydrazines

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