Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds

Autores
Villabrille, Paula Isabel; Palermo, Valeria; Sathicq, Angel Gabriel; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo
Año de publicación
2018
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Background: Molybdophosphoric acid (PMo) is used in heterogeneous catalysis. The incorporation of vanadium in the primary structure and a transition metal in the secondary structure of PMo improves the oxidative and acidity capacity. 4- Dihydropyrimidin-2-(1H)-thiones/-ones (DHPMs) derivatives are relevant because of their biological activities. The development of ecofriendly procedures, such as multicomponent reactions, to prepare DHPMs is an important challenge for organic chemistry. Objective: Study the effect of adding transition metal counterions to 11-molybdo-1- vanadophosphoric acid (PMoV) on its catalytic activity for the synthesis of bioactive DHPMs derivatives. Method: Transition metal-doped heteropolyacid catalysts (PMoV, FePMoV, and CuPMoV) were prepared and characterized by Fourier transform infrared spectroscopy, 31P nuclear magnetic resonance, and diffuse reflectance spectroscopy. The acid properties were determined by potentiometric titration. A series of bioactive DHPMs derivatives, such as monastrol, were synthesized by a one-pot procedure using the catalysts under solvent-free conditions. Results: The incorporation of V, Fe and Cu in the primary or secondary structure of PMo improved the catalytic activity of the materials. The proposed DHPMs synthesis required short reaction time (1 h) and a temperature of 80°C. A correlation between the yields of monastrol and the acid strength or the number of acid sites of the catalysts was observed, namely, FePMoV>CuPMoV>PMoV>PMo. The FePMoV catalyst was easily recycled and reused without appreciable loss of activity. Conclusion: The described method is a simple, clean and environmentally friendly alternative for the preparation of 22 bioactive substituted DHPMs with very good yields and high selectivity.
Fil: Villabrille, Paula Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Palermo, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Materia
3, 4-Dihydropyrimidin-2-(1h)-Thiones/-Ones
Monastrol
Biginelli Reaction
Transition Metal-Doped Heteropolyacid Catalysts
Solvent-Free Synthesis
Multicomponent Reaction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/47310
Acceder
id CONICETDig_7a3c2134797f4786f97f4ba5dd86cf85
oai_identifier_str oai:ri.conicet.gov.ar:11336/47310
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related CompoundsVillabrille, Paula IsabelPalermo, ValeriaSathicq, Angel GabrielVazquez, Patricia GracielaRomanelli, Gustavo Pablo3, 4-Dihydropyrimidin-2-(1h)-Thiones/-OnesMonastrolBiginelli ReactionTransition Metal-Doped Heteropolyacid CatalystsSolvent-Free SynthesisMulticomponent Reactionhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Background: Molybdophosphoric acid (PMo) is used in heterogeneous catalysis. The incorporation of vanadium in the primary structure and a transition metal in the secondary structure of PMo improves the oxidative and acidity capacity. 4- Dihydropyrimidin-2-(1H)-thiones/-ones (DHPMs) derivatives are relevant because of their biological activities. The development of ecofriendly procedures, such as multicomponent reactions, to prepare DHPMs is an important challenge for organic chemistry. Objective: Study the effect of adding transition metal counterions to 11-molybdo-1- vanadophosphoric acid (PMoV) on its catalytic activity for the synthesis of bioactive DHPMs derivatives. Method: Transition metal-doped heteropolyacid catalysts (PMoV, FePMoV, and CuPMoV) were prepared and characterized by Fourier transform infrared spectroscopy, 31P nuclear magnetic resonance, and diffuse reflectance spectroscopy. The acid properties were determined by potentiometric titration. A series of bioactive DHPMs derivatives, such as monastrol, were synthesized by a one-pot procedure using the catalysts under solvent-free conditions. Results: The incorporation of V, Fe and Cu in the primary or secondary structure of PMo improved the catalytic activity of the materials. The proposed DHPMs synthesis required short reaction time (1 h) and a temperature of 80°C. A correlation between the yields of monastrol and the acid strength or the number of acid sites of the catalysts was observed, namely, FePMoV>CuPMoV>PMoV>PMo. The FePMoV catalyst was easily recycled and reused without appreciable loss of activity. Conclusion: The described method is a simple, clean and environmentally friendly alternative for the preparation of 22 bioactive substituted DHPMs with very good yields and high selectivity.Fil: Villabrille, Paula Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Palermo, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaBentham Science Publishers2018-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/47310Villabrille, Paula Isabel; Palermo, Valeria; Sathicq, Angel Gabriel; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds; Bentham Science Publishers; Current Organic Chemistry; 22; 1; 2-2018; 94-1001385-27281875-5348CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/156522/articleinfo:eu-repo/semantics/altIdentifier/doi/10.2174/1385272821666171023153938info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:05:59Zoai:ri.conicet.gov.ar:11336/47310instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-10 13:05:59.33CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
title Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
spellingShingle Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
Villabrille, Paula Isabel
3, 4-Dihydropyrimidin-2-(1h)-Thiones/-Ones
Monastrol
Biginelli Reaction
Transition Metal-Doped Heteropolyacid Catalysts
Solvent-Free Synthesis
Multicomponent Reaction
title_short Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
title_full Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
title_fullStr Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
title_full_unstemmed Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
title_sort Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds
dc.creator.none.fl_str_mv Villabrille, Paula Isabel
Palermo, Valeria
Sathicq, Angel Gabriel
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author Villabrille, Paula Isabel
author_facet Villabrille, Paula Isabel
Palermo, Valeria
Sathicq, Angel Gabriel
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author_role author
author2 Palermo, Valeria
Sathicq, Angel Gabriel
Vazquez, Patricia Graciela
Romanelli, Gustavo Pablo
author2_role author
author
author
author
dc.subject.none.fl_str_mv 3, 4-Dihydropyrimidin-2-(1h)-Thiones/-Ones
Monastrol
Biginelli Reaction
Transition Metal-Doped Heteropolyacid Catalysts
Solvent-Free Synthesis
Multicomponent Reaction
topic 3, 4-Dihydropyrimidin-2-(1h)-Thiones/-Ones
Monastrol
Biginelli Reaction
Transition Metal-Doped Heteropolyacid Catalysts
Solvent-Free Synthesis
Multicomponent Reaction
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Background: Molybdophosphoric acid (PMo) is used in heterogeneous catalysis. The incorporation of vanadium in the primary structure and a transition metal in the secondary structure of PMo improves the oxidative and acidity capacity. 4- Dihydropyrimidin-2-(1H)-thiones/-ones (DHPMs) derivatives are relevant because of their biological activities. The development of ecofriendly procedures, such as multicomponent reactions, to prepare DHPMs is an important challenge for organic chemistry. Objective: Study the effect of adding transition metal counterions to 11-molybdo-1- vanadophosphoric acid (PMoV) on its catalytic activity for the synthesis of bioactive DHPMs derivatives. Method: Transition metal-doped heteropolyacid catalysts (PMoV, FePMoV, and CuPMoV) were prepared and characterized by Fourier transform infrared spectroscopy, 31P nuclear magnetic resonance, and diffuse reflectance spectroscopy. The acid properties were determined by potentiometric titration. A series of bioactive DHPMs derivatives, such as monastrol, were synthesized by a one-pot procedure using the catalysts under solvent-free conditions. Results: The incorporation of V, Fe and Cu in the primary or secondary structure of PMo improved the catalytic activity of the materials. The proposed DHPMs synthesis required short reaction time (1 h) and a temperature of 80°C. A correlation between the yields of monastrol and the acid strength or the number of acid sites of the catalysts was observed, namely, FePMoV>CuPMoV>PMoV>PMo. The FePMoV catalyst was easily recycled and reused without appreciable loss of activity. Conclusion: The described method is a simple, clean and environmentally friendly alternative for the preparation of 22 bioactive substituted DHPMs with very good yields and high selectivity.
Fil: Villabrille, Paula Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Palermo, Valeria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Sathicq, Angel Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Vazquez, Patricia Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
Fil: Romanelli, Gustavo Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina
description Background: Molybdophosphoric acid (PMo) is used in heterogeneous catalysis. The incorporation of vanadium in the primary structure and a transition metal in the secondary structure of PMo improves the oxidative and acidity capacity. 4- Dihydropyrimidin-2-(1H)-thiones/-ones (DHPMs) derivatives are relevant because of their biological activities. The development of ecofriendly procedures, such as multicomponent reactions, to prepare DHPMs is an important challenge for organic chemistry. Objective: Study the effect of adding transition metal counterions to 11-molybdo-1- vanadophosphoric acid (PMoV) on its catalytic activity for the synthesis of bioactive DHPMs derivatives. Method: Transition metal-doped heteropolyacid catalysts (PMoV, FePMoV, and CuPMoV) were prepared and characterized by Fourier transform infrared spectroscopy, 31P nuclear magnetic resonance, and diffuse reflectance spectroscopy. The acid properties were determined by potentiometric titration. A series of bioactive DHPMs derivatives, such as monastrol, were synthesized by a one-pot procedure using the catalysts under solvent-free conditions. Results: The incorporation of V, Fe and Cu in the primary or secondary structure of PMo improved the catalytic activity of the materials. The proposed DHPMs synthesis required short reaction time (1 h) and a temperature of 80°C. A correlation between the yields of monastrol and the acid strength or the number of acid sites of the catalysts was observed, namely, FePMoV>CuPMoV>PMoV>PMo. The FePMoV catalyst was easily recycled and reused without appreciable loss of activity. Conclusion: The described method is a simple, clean and environmentally friendly alternative for the preparation of 22 bioactive substituted DHPMs with very good yields and high selectivity.
publishDate 2018
dc.date.none.fl_str_mv 2018-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/47310
Villabrille, Paula Isabel; Palermo, Valeria; Sathicq, Angel Gabriel; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds; Bentham Science Publishers; Current Organic Chemistry; 22; 1; 2-2018; 94-100
1385-2728
1875-5348
CONICET Digital
CONICET
url http://hdl.handle.net/11336/47310
identifier_str_mv Villabrille, Paula Isabel; Palermo, Valeria; Sathicq, Angel Gabriel; Vazquez, Patricia Graciela; Romanelli, Gustavo Pablo; Transition Metal-doped Heteropolyacid Catalysts for the Suitable Multicomponent Synthesis of Monastrol and Bioactive Related Compounds; Bentham Science Publishers; Current Organic Chemistry; 22; 1; 2-2018; 94-100
1385-2728
1875-5348
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/156522/article
info:eu-repo/semantics/altIdentifier/doi/10.2174/1385272821666171023153938
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Bentham Science Publishers
publisher.none.fl_str_mv Bentham Science Publishers
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.993085

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