New 3H-Indole Synthesis by Fischer’s Method. Part I

Methyl indolenines (4a-c) and (5a-c) were prepared in high yield by a Fischer indole synthesis reaction of o,m-tolylhydrazine hydrochlorides (1a-b) with isopropyl methyl ketone (2) and 2-methylcyclohexanone (3) in acetic acid at room temperature. o,p- Nitrophenylhydrazines (1c-d) were reacted with 2...

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Autores principales: Sajjadifar, Sami, Vahedi, Hooshang, Massoudi, Abdolhossien, Louie, Omid
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257308/
https://www.ncbi.nlm.nih.gov/pubmed/20428058
http://dx.doi.org/10.3390/molecules15042491
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author Sajjadifar, Sami
Vahedi, Hooshang
Massoudi, Abdolhossien
Louie, Omid
author_facet Sajjadifar, Sami
Vahedi, Hooshang
Massoudi, Abdolhossien
Louie, Omid
author_sort Sajjadifar, Sami
collection PubMed
description Methyl indolenines (4a-c) and (5a-c) were prepared in high yield by a Fischer indole synthesis reaction of o,m-tolylhydrazine hydrochlorides (1a-b) with isopropyl methyl ketone (2) and 2-methylcyclohexanone (3) in acetic acid at room temperature. o,p- Nitrophenylhydrazines (1c-d) were reacted with 2-methylcyclohexanone (3) in acetic acid at reflux to give nitroindolenines (5d-e), while the attempted reactions of o,p-nitrohydrazines with isopropyl methyl ketone (2) in acetic acid were not successful. Compounds (1c-d) were reacted with isopropyl methyl ketone (2) in acetic acid/HCl to give 2,3,3-trimethyl-5-nitro-indolenine (4e) and 2,3,3-trimethyl-7-nitroindolenine (4d).
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spelling pubmed-62573082018-11-30 New 3H-Indole Synthesis by Fischer’s Method. Part I Sajjadifar, Sami Vahedi, Hooshang Massoudi, Abdolhossien Louie, Omid Molecules Article Methyl indolenines (4a-c) and (5a-c) were prepared in high yield by a Fischer indole synthesis reaction of o,m-tolylhydrazine hydrochlorides (1a-b) with isopropyl methyl ketone (2) and 2-methylcyclohexanone (3) in acetic acid at room temperature. o,p- Nitrophenylhydrazines (1c-d) were reacted with 2-methylcyclohexanone (3) in acetic acid at reflux to give nitroindolenines (5d-e), while the attempted reactions of o,p-nitrohydrazines with isopropyl methyl ketone (2) in acetic acid were not successful. Compounds (1c-d) were reacted with isopropyl methyl ketone (2) in acetic acid/HCl to give 2,3,3-trimethyl-5-nitro-indolenine (4e) and 2,3,3-trimethyl-7-nitroindolenine (4d). Molecular Diversity Preservation International 2010-04-08 /pmc/articles/PMC6257308/ /pubmed/20428058 http://dx.doi.org/10.3390/molecules15042491 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Sajjadifar, Sami
Vahedi, Hooshang
Massoudi, Abdolhossien
Louie, Omid
New 3H-Indole Synthesis by Fischer’s Method. Part I
title New 3H-Indole Synthesis by Fischer’s Method. Part I
title_full New 3H-Indole Synthesis by Fischer’s Method. Part I
title_fullStr New 3H-Indole Synthesis by Fischer’s Method. Part I
title_full_unstemmed New 3H-Indole Synthesis by Fischer’s Method. Part I
title_short New 3H-Indole Synthesis by Fischer’s Method. Part I
title_sort new 3h-indole synthesis by fischer’s method. part i
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257308/
https://www.ncbi.nlm.nih.gov/pubmed/20428058
http://dx.doi.org/10.3390/molecules15042491
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AT louieomid new3hindolesynthesisbyfischersmethodparti

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