Publicação
Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines
| Resumo: | 2-(2-Aminophenyl)quinazoline-4-amines were selectively acylated at the phenylamino group by anhydrides, isocyanates or acyl chlorides, at room temperature. A similar selectivity was obtained in the reaction with ethoxymethylene derivatives and orthoesters. Acylation of the exocyclic imino substituent in the quinazolino-quinazoline tetracyclic structure also occurred under mild conditions with acetic anhydride and isocyanates. Hydrolysis to release the aniline substituent was performed with concd HCl (1 equiv at 60 °C) and with 3 M NaOH (3 equiv, rt), leading to the formylated derivative or cleaving the acyl group in the heterocyclic amine. |
|---|---|
| Autores principais: | Marinho, Elina Margarida Ribeiro |
| Outros Autores: | Proença, M. Fernanda R. P. |
| Assunto: | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| Ano: | 2016 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1866876904098758656 |
|---|---|
| author | Marinho, Elina Margarida Ribeiro |
| author2 | Proença, M. Fernanda R. P. |
| author2_role | author |
| author_facet | Marinho, Elina Margarida Ribeiro Proença, M. Fernanda R. P. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Marinho, Elina Margarida Ribeiro\"},{\"Person.name\":\"Proença, M. Fernanda R. P.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Marinho, Elina Margarida Ribeiro Proença, M. Fernanda R. P. |
| datacite.date.Accepted.fl_str_mv | 2016-01-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| datacite.subjects.subject.fl_str_mv | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| datacite.titles.title.fl_str_mv | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Marinho, Elina Margarida Ribeiro Proença, M. Fernanda R. P. |
| dc.date.Accepted.fl_str_mv | 2016-01-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/51950 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Elsevier |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| dc.subject.none.fl_str_mv | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| dc.title.fl_str_mv | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | 2-(2-Aminophenyl)quinazoline-4-amines were selectively acylated at the phenylamino group by anhydrides, isocyanates or acyl chlorides, at room temperature. A similar selectivity was obtained in the reaction with ethoxymethylene derivatives and orthoesters. Acylation of the exocyclic imino substituent in the quinazolino-quinazoline tetracyclic structure also occurred under mild conditions with acetic anhydride and isocyanates. Hydrolysis to release the aniline substituent was performed with concd HCl (1 equiv at 60 °C) and with 3 M NaOH (3 equiv, rt), leading to the formylated derivative or cleaving the acyl group in the heterocyclic amine. |
| dirty | 0 |
| eu_rights_str_mv | restrictedAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/46168716-1540-4729-b746-800f3cecf55f/download |
| id | rum_aeb9becd4e109f3ab4bbfe82c3d9183c |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/51950 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
| network_acronym_str | rum |
| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/51950 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Marinho, Elina Margarida Ribeiro Proença, M. Fernanda R. P. |
| publishDate | 2016 |
| publisher.none.fl_str_mv | Elsevier |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engElsevierpor2-(2-Aminophenyl)quinazoline-4-amines were selectively acylated at the phenylamino group by anhydrides, isocyanates or acyl chlorides, at room temperature. A similar selectivity was obtained in the reaction with ethoxymethylene derivatives and orthoesters. Acylation of the exocyclic imino substituent in the quinazolino-quinazoline tetracyclic structure also occurred under mild conditions with acetic anhydride and isocyanates. Hydrolysis to release the aniline substituent was performed with concd HCl (1 equiv at 60 °C) and with 3 M NaOH (3 equiv, rt), leading to the formylated derivative or cleaving the acyl group in the heterocyclic amine.application/pdfporReactivity and regioselectivity in the acylation of 2,4-diaminoquinazolinesMarinho, Elina Margarida RibeiroProença, M. Fernanda R. P.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf0040-4020DOIIsPartOf10.1016/j.tet.2016.06.00320162016-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/51950http://purl.org/coar/access_right/c_16ecrestricted accessAcyl chloridesIsocyanatesAnhydridesAcylation4-aminoquinazolines650395 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/46168716-1540-4729-b746-800f3cecf55f/download |
| spellingShingle | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines Marinho, Elina Margarida Ribeiro Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| status | SINGLETON |
| subject.fl_str_mv | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| title | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| title_full | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| title_fullStr | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| title_full_unstemmed | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| title_short | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| title_sort | Reactivity and regioselectivity in the acylation of 2,4-diaminoquinazolines |
| topic | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| topic_facet | Acyl chlorides Isocyanates Anhydrides Acylation 4-aminoquinazolines |
| url | https://hdl.handle.net/1822/51950 |
| visible | 1 |