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Abstract:

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.

Registro:

Documento: Artículo
Título: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
Autor:Pis Diez, C.M.; Fernandez, J.F.; Di Venosa, G.; Casas, A.; Pis Diez, R.; Palermo, J.A.
Filiación:Universidad de Buenos Aires, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, Pabellón 2-(1428), Buenos Aires, Argentina
CONICET-Universidad de Buenos Aires, Unidad de Microanálisis y Métodos Físicos en Química Orgánica, Buenos Aires, Argentina
Centro de Investigaciones Sobre Porfirinas y Porfirias (CIPYP), CONICET, Hospital de Clínicas José de San Martin, Universidad de Buenos Aires, Córdoba 2351, 1er subsuelo, Ciudad de Buenos Aires, Buenos Aires, 1120AAF, Argentina
CEQUINOR (CONICET-CCT-La Plata, UNLP), Bvd 120 N1465, La Plata, 1900, Argentina
Palabras clave:Catalysis; Cell culture; Chains; Isomerization; Ketones; Olefins; Reaction intermediates; Basic media; Cell lines; Diels-Alder reaction; Naphthoquinones; P-benzoquinone; Reaction conditions; Theoretical study; Isomers
Año:2018
Volumen:8
Número:63
Página de inicio:35998
Página de fin:36006
DOI: http://dx.doi.org/10.1039/c8ra05208e
Título revista:RSC Advances
Título revista abreviado:RSC Adv.
ISSN:20462069
CODEN:RSCAC
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_20462069_v8_n63_p35998_PisDiez

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Citas:

---------- APA ----------
Pis Diez, C.M., Fernandez, J.F., Di Venosa, G., Casas, A., Pis Diez, R. & Palermo, J.A. (2018) . 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. RSC Advances, 8(63), 35998-36006.
http://dx.doi.org/10.1039/c8ra05208e
---------- CHICAGO ----------
Pis Diez, C.M., Fernandez, J.F., Di Venosa, G., Casas, A., Pis Diez, R., Palermo, J.A. "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" . RSC Advances 8, no. 63 (2018) : 35998-36006.
http://dx.doi.org/10.1039/c8ra05208e
---------- MLA ----------
Pis Diez, C.M., Fernandez, J.F., Di Venosa, G., Casas, A., Pis Diez, R., Palermo, J.A. "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" . RSC Advances, vol. 8, no. 63, 2018, pp. 35998-36006.
http://dx.doi.org/10.1039/c8ra05208e
---------- VANCOUVER ----------
Pis Diez, C.M., Fernandez, J.F., Di Venosa, G., Casas, A., Pis Diez, R., Palermo, J.A. 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. RSC Adv. 2018;8(63):35998-36006.
http://dx.doi.org/10.1039/c8ra05208e