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
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2006 |
| Outros Autores: | , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) |
| Texto Completo: | https://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. |
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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/PDFhttps://hdl.handle.net/10316/5070https://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:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2022-08-30T15:00:49Zoai:estudogeral.uc.pt:10316/5070Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-29T05:24:18.376402Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse |
| 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 |
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2006 |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
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https://hdl.handle.net/10316/5070 https://hdl.handle.net/10316/5070 https://doi.org/10.1016/j.tet.2006.08.029 |
| url |
https://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 |
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info:eu-repo/semantics/openAccess |
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openAccess |
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aplication/PDF |
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Elsevier |
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Elsevier |
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Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) |
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