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 (Z...

Descripción completa

Guardado en:
Detalles Bibliográficos
Publicado: 2018
Materias:
Catalysis
Cell culture
Chains
Isomerization
Ketones
Olefins
Reaction intermediates
Basic media
Cell lines
Diels-Alder reaction
Naphthoquinones
P-benzoquinone
Reaction conditions
Theoretical study
Isomers
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v8_n63_p35998_PisDiez
http://hdl.handle.net/20.500.12110/paper_20462069_v8_n63_p35998_PisDiez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_20462069_v8_n63_p35998_PisDiez
record_format dspace
spelling paper:paper_20462069_v8_n63_p35998_PisDiez2023-06-08T16:33:46Z 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 Catalysis Cell culture Chains Isomerization Ketones Olefins Reaction intermediates Basic media Cell lines Diels-Alder reaction Naphthoquinones P-benzoquinone Reaction conditions Theoretical study Isomers 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. © 2018 The Royal Society of Chemistry. 2018 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v8_n63_p35998_PisDiez http://hdl.handle.net/20.500.12110/paper_20462069_v8_n63_p35998_PisDiez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Catalysis
Cell culture
Chains
Isomerization
Ketones
Olefins
Reaction intermediates
Basic media
Cell lines
Diels-Alder reaction
Naphthoquinones
P-benzoquinone
Reaction conditions
Theoretical study
Isomers
spellingShingle Catalysis
Cell culture
Chains
Isomerization
Ketones
Olefins
Reaction intermediates
Basic media
Cell lines
Diels-Alder reaction
Naphthoquinones
P-benzoquinone
Reaction conditions
Theoretical study
Isomers
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 Catalysis
Cell culture
Chains
Isomerization
Ketones
Olefins
Reaction intermediates
Basic media
Cell lines
Diels-Alder reaction
Naphthoquinones
P-benzoquinone
Reaction conditions
Theoretical study
Isomers
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. © 2018 The Royal Society of Chemistry.
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 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v8_n63_p35998_PisDiez
http://hdl.handle.net/20.500.12110/paper_20462069_v8_n63_p35998_PisDiez
_version_ 1768541772809502720

Ejemplares similares