Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates

Detalhes bibliográficos
Autor(a) principal: Soares, Maria I. L.
Data de Publicação: 2021
Outros Autores: Gomes, Clara S. B., Oliveira, M. Conceição, Marçalo, Joaquim, Pinho e Melo, Teresa M. V. D.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/107453
https://doi.org/10.1039/d1ob01130h
Resumo: The DABCO-catalyzed [3 + 3] annulation between 3-nitro-2H-chromenes and benzyl 2,3-butadienoate has been developed as a route to 5H-chromeno[3,4-b]pyridine derivatives. Under optimal reaction conditions, 5H-chromeno[3,4-b]pyridines incorporating two allenoate units were obtained in moderate to good yields (30-76%). The same type of transformation could be carried out using butynoates as allene surrogates. Mechanistic studies by mass spectrometry allowed the identification of the key intermediates involved in the reaction mechanism. The reported synthetic methodology represents an entirely new approach for the synthesis of the 5H-chromeno[3,4-b]pyridine core structure based on allene chemistry.
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spelling Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoatesThe DABCO-catalyzed [3 + 3] annulation between 3-nitro-2H-chromenes and benzyl 2,3-butadienoate has been developed as a route to 5H-chromeno[3,4-b]pyridine derivatives. Under optimal reaction conditions, 5H-chromeno[3,4-b]pyridines incorporating two allenoate units were obtained in moderate to good yields (30-76%). The same type of transformation could be carried out using butynoates as allene surrogates. Mechanistic studies by mass spectrometry allowed the identification of the key intermediates involved in the reaction mechanism. The reported synthetic methodology represents an entirely new approach for the synthesis of the 5H-chromeno[3,4-b]pyridine core structure based on allene chemistry.Royal Society of Chemistry2021-11-18info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/107453http://hdl.handle.net/10316/107453https://doi.org/10.1039/d1ob01130hengSoares, Maria I. L.Gomes, Clara S. B.Oliveira, M. ConceiçãoMarçalo, JoaquimPinho e Melo, Teresa M. V. D.info: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:RCAAP2023-07-17T18:12:56Zoai:estudogeral.uc.pt:10316/107453Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:23:48.463279Repositório 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 Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
title Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
spellingShingle Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
Soares, Maria I. L.
title_short Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
title_full Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
title_fullStr Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
title_full_unstemmed Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
title_sort Synthesis of 5H-chromeno[3,4-b]pyridines via DABCO-catalyzed [3 + 3] annulation of 3-nitro-2H-chromenes and allenoates
author Soares, Maria I. L.
author_facet Soares, Maria I. L.
Gomes, Clara S. B.
Oliveira, M. Conceição
Marçalo, Joaquim
Pinho e Melo, Teresa M. V. D.
author_role author
author2 Gomes, Clara S. B.
Oliveira, M. Conceição
Marçalo, Joaquim
Pinho e Melo, Teresa M. V. D.
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Soares, Maria I. L.
Gomes, Clara S. B.
Oliveira, M. Conceição
Marçalo, Joaquim
Pinho e Melo, Teresa M. V. D.
description The DABCO-catalyzed [3 + 3] annulation between 3-nitro-2H-chromenes and benzyl 2,3-butadienoate has been developed as a route to 5H-chromeno[3,4-b]pyridine derivatives. Under optimal reaction conditions, 5H-chromeno[3,4-b]pyridines incorporating two allenoate units were obtained in moderate to good yields (30-76%). The same type of transformation could be carried out using butynoates as allene surrogates. Mechanistic studies by mass spectrometry allowed the identification of the key intermediates involved in the reaction mechanism. The reported synthetic methodology represents an entirely new approach for the synthesis of the 5H-chromeno[3,4-b]pyridine core structure based on allene chemistry.
publishDate 2021
dc.date.none.fl_str_mv 2021-11-18
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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dc.identifier.uri.fl_str_mv http://hdl.handle.net/10316/107453
http://hdl.handle.net/10316/107453
https://doi.org/10.1039/d1ob01130h
url http://hdl.handle.net/10316/107453
https://doi.org/10.1039/d1ob01130h
dc.language.iso.fl_str_mv eng
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dc.publisher.none.fl_str_mv Royal Society of Chemistry
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