Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening

Autores
Cui, Shaoying; Arza, Carlos R.; Froimowicz, Pablo; Ishida, Hatsuo
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In this study, 2-(aminomethyl)phenol and its derivatives, the reactants for 2-substituted 1,3-benzoxazines, are synthesized by HCl hydrolysis from the typical benzoxazines. The phenol/ aniline-based mono-oxazine benzoxazine, PH-a, and the bisphenol A/aniline-based bis-oxazine benzoxazine, BA-a, are used as examples to demonstrate the feasibility of this new approach. Their chemical structures are characterized by nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman spectroscopies, and are further verified by elementary analysis. Their thermal properties are studied by differential scanning calorimetry (DSC). These two 2-(aminomethyl) phenolic derivatives are reacted with paraformaldehyde to close the oxazine rings. A benzoxazine with a phenyl substituent at the 2-position of the oxazine ring is obtained from the 2-(phenylamino)methyl)phenol (hPH-a) and benzaldehyde. All these results highlight the success of the HCl hydrolysis and the formation of stable intermediates, namely 2-(aminomethyl) phenolic derivatives, from readily available benzoxazine monomers. This further demonstrates the feasibility of using these intermediates as reactants for a novel benzoxazine synthesis.
Fil: Cui, Shaoying. Sichuan University; China
Fil: Arza, Carlos R.. Case Western Reserve University; Estados Unidos
Fil: Froimowicz, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; Argentina. Case Western Reserve University; Estados Unidos
Fil: Ishida, Hatsuo. Case Western Reserve University; Estados Unidos
Materia
2-SUBSTITUTED 1,3-BENZOXAZINE
HCL HYDROLYSIS
RING OPENING
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:11336/129678
Acceder
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network_acronym_str CONICETDig
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network_name_str CONICET Digital (CONICET)
spelling Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-OpeningCui, ShaoyingArza, Carlos R.Froimowicz, PabloIshida, Hatsuo2-SUBSTITUTED 1,3-BENZOXAZINEHCL HYDROLYSISRING OPENINGhttps://purl.org/becyt/ford/2.5https://purl.org/becyt/ford/2In this study, 2-(aminomethyl)phenol and its derivatives, the reactants for 2-substituted 1,3-benzoxazines, are synthesized by HCl hydrolysis from the typical benzoxazines. The phenol/ aniline-based mono-oxazine benzoxazine, PH-a, and the bisphenol A/aniline-based bis-oxazine benzoxazine, BA-a, are used as examples to demonstrate the feasibility of this new approach. Their chemical structures are characterized by nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman spectroscopies, and are further verified by elementary analysis. Their thermal properties are studied by differential scanning calorimetry (DSC). These two 2-(aminomethyl) phenolic derivatives are reacted with paraformaldehyde to close the oxazine rings. A benzoxazine with a phenyl substituent at the 2-position of the oxazine ring is obtained from the 2-(phenylamino)methyl)phenol (hPH-a) and benzaldehyde. All these results highlight the success of the HCl hydrolysis and the formation of stable intermediates, namely 2-(aminomethyl) phenolic derivatives, from readily available benzoxazine monomers. This further demonstrates the feasibility of using these intermediates as reactants for a novel benzoxazine synthesis.Fil: Cui, Shaoying. Sichuan University; ChinaFil: Arza, Carlos R.. Case Western Reserve University; Estados UnidosFil: Froimowicz, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; Argentina. Case Western Reserve University; Estados UnidosFil: Ishida, Hatsuo. Case Western Reserve University; Estados UnidosMolecular Diversity Preservation International2020-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/129678Cui, Shaoying; Arza, Carlos R.; Froimowicz, Pablo; Ishida, Hatsuo; Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening; Molecular Diversity Preservation International; Polymers; 12; 3; 3-2020; 1-132073-4360CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/polym12030694info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:22:54Zoai:ri.conicet.gov.ar:11336/129678instacron: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 13:22:54.314CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
title Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
spellingShingle Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
Cui, Shaoying
2-SUBSTITUTED 1,3-BENZOXAZINE
HCL HYDROLYSIS
RING OPENING
title_short Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
title_full Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
title_fullStr Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
title_full_unstemmed Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
title_sort Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening
dc.creator.none.fl_str_mv Cui, Shaoying
Arza, Carlos R.
Froimowicz, Pablo
Ishida, Hatsuo
author Cui, Shaoying
author_facet Cui, Shaoying
Arza, Carlos R.
Froimowicz, Pablo
Ishida, Hatsuo
author_role author
author2 Arza, Carlos R.
Froimowicz, Pablo
Ishida, Hatsuo
author2_role author
author
author
dc.subject.none.fl_str_mv 2-SUBSTITUTED 1,3-BENZOXAZINE
HCL HYDROLYSIS
RING OPENING
topic 2-SUBSTITUTED 1,3-BENZOXAZINE
HCL HYDROLYSIS
RING OPENING
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.5
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv In this study, 2-(aminomethyl)phenol and its derivatives, the reactants for 2-substituted 1,3-benzoxazines, are synthesized by HCl hydrolysis from the typical benzoxazines. The phenol/ aniline-based mono-oxazine benzoxazine, PH-a, and the bisphenol A/aniline-based bis-oxazine benzoxazine, BA-a, are used as examples to demonstrate the feasibility of this new approach. Their chemical structures are characterized by nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman spectroscopies, and are further verified by elementary analysis. Their thermal properties are studied by differential scanning calorimetry (DSC). These two 2-(aminomethyl) phenolic derivatives are reacted with paraformaldehyde to close the oxazine rings. A benzoxazine with a phenyl substituent at the 2-position of the oxazine ring is obtained from the 2-(phenylamino)methyl)phenol (hPH-a) and benzaldehyde. All these results highlight the success of the HCl hydrolysis and the formation of stable intermediates, namely 2-(aminomethyl) phenolic derivatives, from readily available benzoxazine monomers. This further demonstrates the feasibility of using these intermediates as reactants for a novel benzoxazine synthesis.
Fil: Cui, Shaoying. Sichuan University; China
Fil: Arza, Carlos R.. Case Western Reserve University; Estados Unidos
Fil: Froimowicz, Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay. Instituto de Tecnología en Polímeros y Nanotecnología. Universidad de Buenos Aires. Facultad de Ingeniería. Instituto de Tecnología en Polímeros y Nanotecnología; Argentina. Case Western Reserve University; Estados Unidos
Fil: Ishida, Hatsuo. Case Western Reserve University; Estados Unidos
description In this study, 2-(aminomethyl)phenol and its derivatives, the reactants for 2-substituted 1,3-benzoxazines, are synthesized by HCl hydrolysis from the typical benzoxazines. The phenol/ aniline-based mono-oxazine benzoxazine, PH-a, and the bisphenol A/aniline-based bis-oxazine benzoxazine, BA-a, are used as examples to demonstrate the feasibility of this new approach. Their chemical structures are characterized by nuclear magnetic resonance (NMR), Fourier transform infrared (FTIR) and Raman spectroscopies, and are further verified by elementary analysis. Their thermal properties are studied by differential scanning calorimetry (DSC). These two 2-(aminomethyl) phenolic derivatives are reacted with paraformaldehyde to close the oxazine rings. A benzoxazine with a phenyl substituent at the 2-position of the oxazine ring is obtained from the 2-(phenylamino)methyl)phenol (hPH-a) and benzaldehyde. All these results highlight the success of the HCl hydrolysis and the formation of stable intermediates, namely 2-(aminomethyl) phenolic derivatives, from readily available benzoxazine monomers. This further demonstrates the feasibility of using these intermediates as reactants for a novel benzoxazine synthesis.
publishDate 2020
dc.date.none.fl_str_mv 2020-03
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/11336/129678
Cui, Shaoying; Arza, Carlos R.; Froimowicz, Pablo; Ishida, Hatsuo; Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening; Molecular Diversity Preservation International; Polymers; 12; 3; 3-2020; 1-13
2073-4360
CONICET Digital
CONICET
url http://hdl.handle.net/11336/129678
identifier_str_mv Cui, Shaoying; Arza, Carlos R.; Froimowicz, Pablo; Ishida, Hatsuo; Developing Further Versatility in Benzoxazine Synthesis via Hydrolytic Ring-Opening; Molecular Diversity Preservation International; Polymers; 12; 3; 3-2020; 1-13
2073-4360
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/polym12030694
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 Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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 12.48226

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