Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles

Detalhes bibliográficos
Autor(a) principal: Cardoso, Ana L.
Data de Publicação: 2006
Outros Autores: Kaczor, Agnieszka, Silva, Artur M. S., Fausto, Rui, Melo, Teresa M. V. D. Pinho e, Gonsalves, António M. d'A. Rocha
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/5070
https://doi.org/10.1016/j.tet.2006.08.029
Resumo: The 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-chemistry calculations were carried out allowing the rationalization of the observed stereoselective formation of the anti-dipole.
id RCAP_b6ccddada2984f7c45fe6bb47dfcfe11
oai_identifier_str oai:estudogeral.uc.pt:10316/5070
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazolesAzomethine ylides1,3-Dipolar cycloaddition1,3-Thiazolidine-4-carboxylic acids5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazolesThe 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-chemistry calculations were carried out allowing the rationalization of the observed stereoselective formation of the anti-dipole.http://www.sciencedirect.com/science/article/B6THR-4KSSW69-5/1/f6fd75ae8164720ba1de8d3b3a44ed03Elsevier2006info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleaplication/PDFhttp://hdl.handle.net/10316/5070http://hdl.handle.net/10316/5070https://doi.org/10.1016/j.tet.2006.08.029engTetrahedron. 62:42 (2006) 9861-9871Cardoso, Ana L.Kaczor, AgnieszkaSilva, Artur M. S.Fausto, RuiMelo, Teresa M. V. D. Pinho eGonsalves, António M. d'A. Rochainfo: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:RCAAP2022-08-30T15:00:49Zoai:estudogeral.uc.pt:10316/5070Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:01:40.746601Repositório 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 Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
title Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
spellingShingle Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
Cardoso, Ana L.
Azomethine ylides
1,3-Dipolar cycloaddition
1,3-Thiazolidine-4-carboxylic acids
5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
title_short Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
title_full Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
title_fullStr Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
title_full_unstemmed Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
title_sort Intermolecular cycloaddition of nonstabilized azomethine ylides generated from 1,3-thiazolidine-4-carboxylic acids: synthesis of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
author Cardoso, Ana L.
author_facet Cardoso, Ana L.
Kaczor, Agnieszka
Silva, Artur M. S.
Fausto, Rui
Melo, Teresa M. V. D. Pinho e
Gonsalves, António M. d'A. Rocha
author_role author
author2 Kaczor, Agnieszka
Silva, Artur M. S.
Fausto, Rui
Melo, Teresa M. V. D. Pinho e
Gonsalves, António M. d'A. Rocha
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Cardoso, Ana L.
Kaczor, Agnieszka
Silva, Artur M. S.
Fausto, Rui
Melo, Teresa M. V. D. Pinho e
Gonsalves, António M. d'A. Rocha
dc.subject.por.fl_str_mv Azomethine ylides
1,3-Dipolar cycloaddition
1,3-Thiazolidine-4-carboxylic acids
5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
topic Azomethine ylides
1,3-Dipolar cycloaddition
1,3-Thiazolidine-4-carboxylic acids
5,7a-Dihydro-1H,3H-pyrrolo[1,2-c]thiazoles
description The 1,3-dipolar cycloaddition of dimethyl acetylenedicarboxylate with nonstabilized azomethine ylides, generated via the decarboxylative condensation of 1,3-thiazolidine-4-carboxylic acids with aldehydes, afforded 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazole derivatives. 2-Substituted-1,3-thiazolidine-4-carboxylic acids led to the stereoselective formation of 5,7a-dihydro-1H,3H-pyrrolo[1,2-c]thiazoles. Quantum-chemistry calculations were carried out allowing the rationalization of the observed stereoselective formation of the anti-dipole.
publishDate 2006
dc.date.none.fl_str_mv 2006
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/10316/5070
http://hdl.handle.net/10316/5070
https://doi.org/10.1016/j.tet.2006.08.029
url http://hdl.handle.net/10316/5070
https://doi.org/10.1016/j.tet.2006.08.029
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Tetrahedron. 62:42 (2006) 9861-9871
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.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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_ 1799133907451379712

Registros relacionados