Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones

Autores
Peláez, Walter José; Szakonyi, Zsolt; Fülöp, Ferenc; Yranzo, Gloria Inés
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
—Some cis/trans-2-thioquinazolin-4-ones and their 2,4-dione analogs were subjected to flash vacuum pyrolysis. The cis- and trans-thio compounds reacted at lower temperatures than the cis- and trans-dioxo analogs, showing a lower thermal stability. All of these compounds afforded similar reactions: ring opening to the corresponding iso(thio)cyanate, the loss of H and NCS to form three isomeric cyclohexadienes and then aromatization to form the corresponding benzamide. The cis-dioxo compound also underwent a competitive retro Diels–Alder (RDA) reaction to form 3-phenylpyrimidine-2,4(1H,3H-dione(3-phenyluracil)) and butadiene. Kinetic measurements of the ring opening reaction supported a concerted b-elimination as the most probable mechanism.
Fil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Szakonyi, Zsolt. University of Szeged; Hungría
Fil: Fülöp, Ferenc. University of Szeged; Hungría
Fil: Yranzo, Gloria Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Materia
Flash vacuum pyrolysis
Retro Diels?Alder
Isothiocyanates
Isocyanates
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:11336/240967
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-onesPeláez, Walter JoséSzakonyi, ZsoltFülöp, FerencYranzo, Gloria InésFlash vacuum pyrolysisRetro Diels?AlderIsothiocyanatesIsocyanateshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1—Some cis/trans-2-thioquinazolin-4-ones and their 2,4-dione analogs were subjected to flash vacuum pyrolysis. The cis- and trans-thio compounds reacted at lower temperatures than the cis- and trans-dioxo analogs, showing a lower thermal stability. All of these compounds afforded similar reactions: ring opening to the corresponding iso(thio)cyanate, the loss of H and NCS to form three isomeric cyclohexadienes and then aromatization to form the corresponding benzamide. The cis-dioxo compound also underwent a competitive retro Diels–Alder (RDA) reaction to form 3-phenylpyrimidine-2,4(1H,3H-dione(3-phenyluracil)) and butadiene. Kinetic measurements of the ring opening reaction supported a concerted b-elimination as the most probable mechanism.Fil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaFil: Szakonyi, Zsolt. University of Szeged; HungríaFil: Fülöp, Ferenc. University of Szeged; HungríaFil: Yranzo, Gloria Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; ArgentinaPergamon-Elsevier Science Ltd2008-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/240967Peláez, Walter José; Szakonyi, Zsolt; Fülöp, Ferenc; Yranzo, Gloria Inés; Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones; Pergamon-Elsevier Science Ltd; Tetrahedron; 64; 6; 2-2008; 1049-10570040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402007012094info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2007.07.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:12Zoai:ri.conicet.gov.ar:11336/240967instacron: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:34982025-09-29 10:33:12.31CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
title Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
spellingShingle Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
Peláez, Walter José
Flash vacuum pyrolysis
Retro Diels?Alder
Isothiocyanates
Isocyanates
title_short Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
title_full Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
title_fullStr Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
title_full_unstemmed Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
title_sort Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones
dc.creator.none.fl_str_mv Peláez, Walter José
Szakonyi, Zsolt
Fülöp, Ferenc
Yranzo, Gloria Inés
author Peláez, Walter José
author_facet Peláez, Walter José
Szakonyi, Zsolt
Fülöp, Ferenc
Yranzo, Gloria Inés
author_role author
author2 Szakonyi, Zsolt
Fülöp, Ferenc
Yranzo, Gloria Inés
author2_role author
author
author
dc.subject.none.fl_str_mv Flash vacuum pyrolysis
Retro Diels?Alder
Isothiocyanates
Isocyanates
topic Flash vacuum pyrolysis
Retro Diels?Alder
Isothiocyanates
Isocyanates
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv —Some cis/trans-2-thioquinazolin-4-ones and their 2,4-dione analogs were subjected to flash vacuum pyrolysis. The cis- and trans-thio compounds reacted at lower temperatures than the cis- and trans-dioxo analogs, showing a lower thermal stability. All of these compounds afforded similar reactions: ring opening to the corresponding iso(thio)cyanate, the loss of H and NCS to form three isomeric cyclohexadienes and then aromatization to form the corresponding benzamide. The cis-dioxo compound also underwent a competitive retro Diels–Alder (RDA) reaction to form 3-phenylpyrimidine-2,4(1H,3H-dione(3-phenyluracil)) and butadiene. Kinetic measurements of the ring opening reaction supported a concerted b-elimination as the most probable mechanism.
Fil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
Fil: Szakonyi, Zsolt. University of Szeged; Hungría
Fil: Fülöp, Ferenc. University of Szeged; Hungría
Fil: Yranzo, Gloria Inés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina
description —Some cis/trans-2-thioquinazolin-4-ones and their 2,4-dione analogs were subjected to flash vacuum pyrolysis. The cis- and trans-thio compounds reacted at lower temperatures than the cis- and trans-dioxo analogs, showing a lower thermal stability. All of these compounds afforded similar reactions: ring opening to the corresponding iso(thio)cyanate, the loss of H and NCS to form three isomeric cyclohexadienes and then aromatization to form the corresponding benzamide. The cis-dioxo compound also underwent a competitive retro Diels–Alder (RDA) reaction to form 3-phenylpyrimidine-2,4(1H,3H-dione(3-phenyluracil)) and butadiene. Kinetic measurements of the ring opening reaction supported a concerted b-elimination as the most probable mechanism.
publishDate 2008
dc.date.none.fl_str_mv 2008-02
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/11336/240967
Peláez, Walter José; Szakonyi, Zsolt; Fülöp, Ferenc; Yranzo, Gloria Inés; Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones; Pergamon-Elsevier Science Ltd; Tetrahedron; 64; 6; 2-2008; 1049-1057
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/240967
identifier_str_mv Peláez, Walter José; Szakonyi, Zsolt; Fülöp, Ferenc; Yranzo, Gloria Inés; Flash vacuum pyrolysis (fvp) of some hexahydroquinazolin-4(1H)-ones; Pergamon-Elsevier Science Ltd; Tetrahedron; 64; 6; 2-2008; 1049-1057
0040-4020
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402007012094
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tet.2007.07.010
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
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.070432

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