One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones

A series of novel 1-(N-indolyl)-1,3-butadienes, as (1 : 1) mixtures of the (E) and (Z) dienes, was prepared in one step by base-catalysed isomerization of N-alkylindoles with a terminal butyne chain. The reaction conditions are mild, and in all cases the yields were very high (>90%). The (E) and...

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Autores principales: Pis Diez, Cristian Manuel, Fernández, Julián Francisco, Di Venosa, Gabriela Mariana, Casas, Adriana Gabriela, Pis Diez, Reinaldo, Palermo, Jorge Alejandro
Formato: Articulo
Lenguaje:Inglés
Publicado: 2018
Materias:
Ciencias Exactas
Química
base-catalysed isomerization
reactivity
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/104697
http://hdl.handle.net/11336/95771
https://pubs.rsc.org/en/content/articlelanding/2018/RA/C8RA05208E
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SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-104697
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Ciencias Exactas
Química
base-catalysed isomerization
reactivity
spellingShingle Ciencias Exactas
Química
base-catalysed isomerization
reactivity
Pis Diez, Cristian Manuel
Fernández, Julián Francisco
Di Venosa, Gabriela Mariana
Casas, Adriana Gabriela
Pis Diez, Reinaldo
Palermo, Jorge Alejandro
One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
topic_facet Ciencias Exactas
Química
base-catalysed isomerization
reactivity
description A series of novel 1-(N-indolyl)-1,3-butadienes, as (1 : 1) mixtures of the (E) and (Z) dienes, was prepared in one step by base-catalysed isomerization of N-alkylindoles with a terminal butyne chain. The reaction conditions are mild, and in all cases the yields were very high (>90%). The (E) and (Z) dienes were separable by preparative TLC and could be fully characterized. This isomerization proceeded readily in the case of a butynyl chain, but didn't take place with a pentynyl chain. A mechanism was proposed for this reaction, based on previous studies on the isomerization of alkynes in basic media, and a key intermediate that supports the proposed mechanism could be isolated and fully characterized. A theoretical study of the proposed mechanism was performed by computational methods and the results validated the proposal. The reactivity of the synthesized dienes was studied in Diels–Alder reactions with p-benzoquinone, to obtain a small library of new 5-(N-indolyl)-1,4-naphthoquinones.The lack of reactivity in the case of the (Z) isomers was explained by calculation of the rotational curves of the central bond of the (Z) and (E) dienes. Finally, the cytotoxicity of the new 5-(N-indolyl)-1,4-naphthoquinones was tested against a panel of three cell lines.
format Articulo
Articulo
author Pis Diez, Cristian Manuel
Fernández, Julián Francisco
Di Venosa, Gabriela Mariana
Casas, Adriana Gabriela
Pis Diez, Reinaldo
Palermo, Jorge Alejandro
author_facet Pis Diez, Cristian Manuel
Fernández, Julián Francisco
Di Venosa, Gabriela Mariana
Casas, Adriana Gabriela
Pis Diez, Reinaldo
Palermo, Jorge Alejandro
author_sort Pis Diez, Cristian Manuel
title One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
title_short One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
title_full One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
title_fullStr One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
title_full_unstemmed One-step preparation of novel 1-(N-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(N-indolyl)-naphthoquinones
title_sort one-step preparation of novel 1-(n-indolyl)-1,3-butadienes by base-catalysed isomerization of alkynes as an access to 5-(n-indolyl)-naphthoquinones
publishDate 2018
url http://sedici.unlp.edu.ar/handle/10915/104697
http://hdl.handle.net/11336/95771
https://pubs.rsc.org/en/content/articlelanding/2018/RA/C8RA05208E
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