Publicação
Chromones as versatile building blocks in cycloaddition reactions
| Resumo: | 4H-Chromen-4-ones commonly referred as chromones are a class of naturally occurring heterocyclic compounds implicated in a series of biological and pharmacological properties.[1] It is also an interesting scaffold involved in a range of chemical transformations for the preparation of novel and more complex oxygen-containing heterocyclic derivatives.[2] Following our interest in the chemistry of chromones, we design two different building blocks, 2- [(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones 1 and (E)-2-(4-arylbut-1-en-3-yn-1-yl)-4Hchromen- 4-ones 2, and explore the reactivity of the unsaturated systems in cycloaddition reactions. In the former case, chromones 1 were used as dienes in microwave-assisted Diels–Alder (DA) reactions with various electron-poor and electron-rich dienophiles to provide flavone-type compounds 3.[3] In the latter case, the diene system of chromones 2 was involved in DA reactions with N-methylmaleimide whereas the acetylene moiety react with sodium azide, via 1,3-dipolar cycloaddition reaction, to afford xanthene-1,2,3-triazole dyads 4.[4] In this communication, we will present and discuss the synthetic details and spectroscopic characterization of the main products and some interesting byproducts, as well as the intermediate compounds isolated in each case. |
|---|---|
| Autores principais: | Albuquerque, Hélio |
| Outros Autores: | Santos, Clementina M.M.; Cavaleiro, José; Silva, Artur |
| Ano: | 2017 |
| País: | Portugal |
| Tipo de documento: | póster em conferência |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Instituto Politécnico de Bragança |
| Idioma: | inglês |
| Origem: | Biblioteca Digital do IPB |
| _version_ | 1867173124352507904 |
|---|---|
| author | Albuquerque, Hélio |
| author2 | Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
| author2_role | author author author |
| author_facet | Albuquerque, Hélio Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
| author_role | author |
| contributor_name_str_mv | Biblioteca Digital do IPB |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Albuquerque, Hélio\"},{\"Person.name\":\"Santos, Clementina M.M.\",\"Person.identifier.orcid\":\"0000-0003-4380-7990\"},{\"Person.name\":\"Cavaleiro, José\"},{\"Person.name\":\"Silva, Artur\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Biblioteca Digital do IPB |
| datacite.creators.creator.creatorName.fl_str_mv | Albuquerque, Hélio Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
| datacite.date.Accepted.fl_str_mv | 2017-01-01T00:00:00Z |
| datacite.date.available.fl_str_mv | 2017-11-09T11:02:17Z |
| datacite.date.embargoed.fl_str_mv | 2017-11-09T11:02:17Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.titles.title.fl_str_mv | Chromones as versatile building blocks in cycloaddition reactions |
| dc.contributor.none.fl_str_mv | Biblioteca Digital do IPB |
| dc.creator.none.fl_str_mv | Albuquerque, Hélio Santos, Clementina M.M. Cavaleiro, José Silva, Artur |
| dc.date.Accepted.fl_str_mv | 2017-01-01T00:00:00Z |
| dc.date.available.fl_str_mv | 2017-11-09T11:02:17Z |
| dc.date.embargoed.fl_str_mv | 2017-11-09T11:02:17Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | http://hdl.handle.net/10198/14608 |
| dc.language.none.fl_str_mv | eng |
| dc.rights.cclincense.fl_str_mv | http://creativecommons.org/licenses/by-sa/4.0/ |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.title.fl_str_mv | Chromones as versatile building blocks in cycloaddition reactions |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6670 |
| description | 4H-Chromen-4-ones commonly referred as chromones are a class of naturally occurring heterocyclic compounds implicated in a series of biological and pharmacological properties.[1] It is also an interesting scaffold involved in a range of chemical transformations for the preparation of novel and more complex oxygen-containing heterocyclic derivatives.[2] Following our interest in the chemistry of chromones, we design two different building blocks, 2- [(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones 1 and (E)-2-(4-arylbut-1-en-3-yn-1-yl)-4Hchromen- 4-ones 2, and explore the reactivity of the unsaturated systems in cycloaddition reactions. In the former case, chromones 1 were used as dienes in microwave-assisted Diels–Alder (DA) reactions with various electron-poor and electron-rich dienophiles to provide flavone-type compounds 3.[3] In the latter case, the diene system of chromones 2 was involved in DA reactions with N-methylmaleimide whereas the acetylene moiety react with sodium azide, via 1,3-dipolar cycloaddition reaction, to afford xanthene-1,2,3-triazole dyads 4.[4] In this communication, we will present and discuss the synthetic details and spectroscopic characterization of the main products and some interesting byproducts, as well as the intermediate compounds isolated in each case. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | conferencePoster |
| fulltext.url.fl_str_mv | https://bibliotecadigital.ipb.pt/bitstreams/eabb9888-82a0-4ee7-992f-50cfc0146abf/download |
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| identifier.url.fl_str_mv | http://hdl.handle.net/10198/14608 |
| instacron_str | ipb |
| institution | Instituto Politécnico de Bragança |
| instname_str | Instituto Politécnico de Bragança |
| language | eng |
| network_acronym_str | ipb |
| network_name_str | Biblioteca Digital do IPB |
| oai_identifier_str | oai:bibliotecadigital.ipb.pt:10198/14608 |
| organization_str_mv | urn:organizationAcronym:ipb |
| person_str_mv | Albuquerque, Hélio Santos, Clementina M.M. Santos, Clementina M.M. https://www.ciencia-id.pt/9018-DB9C-C590 9018-DB9C-C590 http://orcid.org/0000-0003-4380-7990 0000-0003-4380-7990 Cavaleiro, José Silva, Artur |
| publishDate | 2017 |
| reponame_str | Biblioteca Digital do IPB |
| repository_id_str | urn:repositoryAcronym:ipb |
| service_str_mv | urn:repositoryAcronym:ipb |
| spelling | engpt_PT4H-Chromen-4-ones commonly referred as chromones are a class of naturally occurring heterocyclic compounds implicated in a series of biological and pharmacological properties.[1] It is also an interesting scaffold involved in a range of chemical transformations for the preparation of novel and more complex oxygen-containing heterocyclic derivatives.[2] Following our interest in the chemistry of chromones, we design two different building blocks, 2- [(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones 1 and (E)-2-(4-arylbut-1-en-3-yn-1-yl)-4Hchromen- 4-ones 2, and explore the reactivity of the unsaturated systems in cycloaddition reactions. In the former case, chromones 1 were used as dienes in microwave-assisted Diels–Alder (DA) reactions with various electron-poor and electron-rich dienophiles to provide flavone-type compounds 3.[3] In the latter case, the diene system of chromones 2 was involved in DA reactions with N-methylmaleimide whereas the acetylene moiety react with sodium azide, via 1,3-dipolar cycloaddition reaction, to afford xanthene-1,2,3-triazole dyads 4.[4] In this communication, we will present and discuss the synthetic details and spectroscopic characterization of the main products and some interesting byproducts, as well as the intermediate compounds isolated in each case.application/pdfpt_PTChromones as versatile building blocks in cycloaddition reactionsAlbuquerque, HélioPersonalSantos, Clementina M.M.DSpacehttp://dspace.org/items/64f662b6-775d-4ea0-bfd7-f527af0ac1a0DSpacehttp://dspace.org/items/64f662b6-775d-4ea0-bfd7-f527af0ac1a0SantosClementina M.M.Ciência IDhttps://www.ciencia-id.pt9018-DB9C-C590ORCIDhttp://orcid.org0000-0003-4380-7990Scopus Author IDhttps://www.scopus.com7201458663Cavaleiro, JoséSilva, ArturHostingInstitutionOrganizationalBiblioteca Digital do IPBe-mailmailto:dspace@ipb.ptdspace@ipb.pt2017-11-09T11:02:17Z20172017-01-01T00:00:00ZHandlehttp://hdl.handle.net/10198/14608http://purl.org/coar/access_right/c_abf2open access3892136 bytesother research producthttp://purl.org/coar/resource_type/c_6670conference poster2017http://creativecommons.org/licenses/by-sa/4.0/http://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://bibliotecadigital.ipb.pt/bitstreams/eabb9888-82a0-4ee7-992f-50cfc0146abf/download26th ISHC CongressRegensburg, Alemanha |
| spellingShingle | Chromones as versatile building blocks in cycloaddition reactions Albuquerque, Hélio |
| status | SINGLETON |
| title | Chromones as versatile building blocks in cycloaddition reactions |
| title_full | Chromones as versatile building blocks in cycloaddition reactions |
| title_fullStr | Chromones as versatile building blocks in cycloaddition reactions |
| title_full_unstemmed | Chromones as versatile building blocks in cycloaddition reactions |
| title_short | Chromones as versatile building blocks in cycloaddition reactions |
| title_sort | Chromones as versatile building blocks in cycloaddition reactions |
| url | http://hdl.handle.net/10198/14608 |
| visible | 1 |