Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions

Detalhes bibliográficos
Autor(a) principal: Soares, Maria I. L.
Data de Publicação: 2008
Outros Autores: Melo, Teresa M. V. D. Pinho e
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/4999
https://doi.org/10.1016/j.tetlet.2008.06.013
Resumo: Azafulvenium methides and diazafulvenium methides have been generated under microwave irradiation from 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2,2-dioxo-1H,3H-pyrazolo[1,5-c]thiazoles, respectively. Pericyclic reactions of these 1,7-dipole intermediates, namely, sigmatropic [1,8]H shifts, 1,7-electrocyclization or [8[pi]+2[pi]] cycloaddition led to the synthesis of a range of pyrrole and pyrazole derivatives. The first evidence for the azafulvenium methides by intermolecular trapping via [8[pi]+2[pi]] cycloaddition is reported.
id RCAP_24fb12f99a76a86c466a7cfa7a601ed1
oai_identifier_str oai:estudogeral.uc.pt:10316/4999
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactionsAzafulvenium methideDiazafulvenium methidePyrrolePyrazoleSigmatropic [1,8]H shifts1,7-Electrocyclization[8[pi]+2[pi]] CycloadditionAzafulvenium methides and diazafulvenium methides have been generated under microwave irradiation from 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2,2-dioxo-1H,3H-pyrazolo[1,5-c]thiazoles, respectively. Pericyclic reactions of these 1,7-dipole intermediates, namely, sigmatropic [1,8]H shifts, 1,7-electrocyclization or [8[pi]+2[pi]] cycloaddition led to the synthesis of a range of pyrrole and pyrazole derivatives. The first evidence for the azafulvenium methides by intermolecular trapping via [8[pi]+2[pi]] cycloaddition is reported.http://www.sciencedirect.com/science/article/B6THS-4SP3SM3-6/1/d6303d9db78919cfe9cd796c1a17d4422008info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleaplication/PDFhttp://hdl.handle.net/10316/4999http://hdl.handle.net/10316/4999https://doi.org/10.1016/j.tetlet.2008.06.013engTetrahedron Letters. 49:33 (2008) 4889-4893Soares, Maria I. L.Melo, Teresa M. V. D. Pinho einfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2020-11-06T16:59:22Zoai:estudogeral.uc.pt:10316/4999Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:40.688765Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
title Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
spellingShingle Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
Soares, Maria I. L.
Azafulvenium methide
Diazafulvenium methide
Pyrrole
Pyrazole
Sigmatropic [1,8]H shifts
1,7-Electrocyclization
[8[pi]+2[pi]] Cycloaddition
title_short Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
title_full Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
title_fullStr Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
title_full_unstemmed Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
title_sort Microwave-assisted generation and reactivity of aza- and diazafulvenium methides: heterocycles via pericyclic reactions
author Soares, Maria I. L.
author_facet Soares, Maria I. L.
Melo, Teresa M. V. D. Pinho e
author_role author
author2 Melo, Teresa M. V. D. Pinho e
author2_role author
dc.contributor.author.fl_str_mv Soares, Maria I. L.
Melo, Teresa M. V. D. Pinho e
dc.subject.por.fl_str_mv Azafulvenium methide
Diazafulvenium methide
Pyrrole
Pyrazole
Sigmatropic [1,8]H shifts
1,7-Electrocyclization
[8[pi]+2[pi]] Cycloaddition
topic Azafulvenium methide
Diazafulvenium methide
Pyrrole
Pyrazole
Sigmatropic [1,8]H shifts
1,7-Electrocyclization
[8[pi]+2[pi]] Cycloaddition
description Azafulvenium methides and diazafulvenium methides have been generated under microwave irradiation from 2,2-dioxo-1H,3H-pyrrolo[1,2-c]thiazoles and 2,2-dioxo-1H,3H-pyrazolo[1,5-c]thiazoles, respectively. Pericyclic reactions of these 1,7-dipole intermediates, namely, sigmatropic [1,8]H shifts, 1,7-electrocyclization or [8[pi]+2[pi]] cycloaddition led to the synthesis of a range of pyrrole and pyrazole derivatives. The first evidence for the azafulvenium methides by intermolecular trapping via [8[pi]+2[pi]] cycloaddition is reported.
publishDate 2008
dc.date.none.fl_str_mv 2008
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10316/4999
http://hdl.handle.net/10316/4999
https://doi.org/10.1016/j.tetlet.2008.06.013
url http://hdl.handle.net/10316/4999
https://doi.org/10.1016/j.tetlet.2008.06.013
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Tetrahedron Letters. 49:33 (2008) 4889-4893
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv aplication/PDF
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
_version_ 1799133907450331136

Registros relacionados