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Synthesis of 4-hydroxy and 6-hydroxyindoles: a Renaissance of the Bischler Reaction

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Заглавие Synthesis of 4-hydroxy and 6-hydroxyindoles: a Renaissance of the Bischler Reaction
 
Автор Sharapov, A. D.
Fatykhov, R. F.
Khalymbadzha, I. A.
Chupakhin, O. N.
 
Тематика 4-HYDROXYINDOLES
6-HYDROXYINDOLES
BISCHLER-MÖHLAU REACTION
 
Описание Received: 02.11.2021. Revised: 09.04.2022. Accepted: 09.04.2022. Available online: 13.04.2022.
This work reveals the possibilities for the synthesis of new 4-hydroxy and 6-hydroxyindoles under the conditions of the modified Bischler-Möhlau reaction.
A distinctive feature of this work is the achievement regioselectivity in the synthesis of these hydroxyindoles.
In addition, the one-step synthesis of two isomeric hydroxyindoles with good yields can be characterized as an undoubted advantage of this work.
This paper belongs to the MOSM2021 Special Issue.
In the present work, we have studied a modified Bischler-Möhlau reaction – synthesis of indoles from benzoin and aniline. Our proposed modification of this method differs from that described earlier in that the reaction is carried out at a lower temperature, which made it possible to improve yields and reduce formation of tarry side products. In addition, unlike previous contradictory works, which described the preparation of a single 4-hydroxy or 6-hydroxy isomer in condensation of m-aminophenol and benzoin, we have obtained both 4-hydroxy and 6-hydroxy isomers.
The Russian Science Foundation (no. 21-13-00382) financially supported this research,
 
Дата 2022-08-23T10:04:31Z
2022-08-23T10:04:31Z
2022-07
 
Тип Article
Journal article (info:eu-repo/semantics/article)
Published version (info:eu-repo/semantics/publishedVersion)
 
Идентификатор Synthesis of 4-hydroxy and 6-hydroxyindoles: a Renaissance of the Bischler Reaction / A. D. Sharapov, R. F. Fatykhov, I. A. Khalymbadzha, O. N. Chupakhin // Chimica Techno Acta. — 2022. — Vol. 9, Supplement: MOSM 2021 Special Issue. — No. 202292S2.
2411-1414
http://elar.urfu.ru/handle/10995/116457
https://www.elibrary.ru/item.asp?id=49334075
10.15826/chimtech.2022.9.2.S2
 
Язык en
 
Связанные ресурсы info:eu-repo/grantAgreement/RSF//21-13-00382
Chimica Techno Acta. 2022. Vol. 9. Supplement
 
Формат application/pdf
 
Издатель Ural Federal University
Уральский федеральный университет