Publicação
Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
| Resumo: | The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles (3). Further reaction with aminoguanidine yielded 5´-cyanomeridianin analogues (4). The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative (8). Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate (3a) with hydroxylamine hydrochloride in basic medium afforded (5-amino-isoxazol-4-yl)-(1H-indol-3-yl)-methanone (5) and the acrylic acid derivative (6) after a short or a long heating, respectively. Unequivocal structural elucidation of the latter compound was achieved from single-crystal X-ray diffraction studies. |
|---|---|
| Autores principais: | Campos, Ana M. F. Oliveira |
| Outros Autores: | Salaheldin, Abdellatif M.; Paz, Filipe A. Almeida; Rodrigues, Lígia M. |
| Assunto: | Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| Ano: | 2011 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1864250218861559808 |
|---|---|
| author | Campos, Ana M. F. Oliveira |
| author2 | Salaheldin, Abdellatif M. Paz, Filipe A. Almeida Rodrigues, Lígia M. |
| author2_role | author author author |
| author_facet | Campos, Ana M. F. Oliveira Salaheldin, Abdellatif M. Paz, Filipe A. Almeida Rodrigues, Lígia M. |
| author_role | author |
| contributor_name_str_mv | Universidade do Minho |
| country_str | PT |
| creators_json_str | [{\"Person.name\":\"Campos, Ana M. F. Oliveira\"},{\"Person.name\":\"Salaheldin, Abdellatif M.\"},{\"Person.name\":\"Paz, Filipe A. Almeida\"},{\"Person.name\":\"Rodrigues, Lígia M.\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Campos, Ana M. F. Oliveira Salaheldin, Abdellatif M. Paz, Filipe A. Almeida Rodrigues, Lígia M. |
| datacite.date.Accepted.fl_str_mv | 2011-11-29T00:00:00Z |
| datacite.date.available.fl_str_mv | 2011-12-13T13:48:20Z |
| datacite.date.embargoed.fl_str_mv | 2011-12-13T13:48:20Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| datacite.titles.title.fl_str_mv | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| dc.contributor.none.fl_str_mv | Universidade do Minho |
| dc.creator.none.fl_str_mv | Campos, Ana M. F. Oliveira Salaheldin, Abdellatif M. Paz, Filipe A. Almeida Rodrigues, Lígia M. |
| dc.date.Accepted.fl_str_mv | 2011-11-29T00:00:00Z |
| dc.date.available.fl_str_mv | 2011-12-13T13:48:20Z |
| dc.date.embargoed.fl_str_mv | 2011-12-13T13:48:20Z |
| dc.format.none.fl_str_mv | application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/15115 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | ARKAT USA, Inc. |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.subject.none.fl_str_mv | Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| dc.title.fl_str_mv | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles (3). Further reaction with aminoguanidine yielded 5´-cyanomeridianin analogues (4). The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative (8). Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate (3a) with hydroxylamine hydrochloride in basic medium afforded (5-amino-isoxazol-4-yl)-(1H-indol-3-yl)-methanone (5) and the acrylic acid derivative (6) after a short or a long heating, respectively. Unequivocal structural elucidation of the latter compound was achieved from single-crystal X-ray diffraction studies. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| fulltext.url.fl_str_mv | https://prod-dspace.uminho.pt/bitstreams/57b8aae0-9cba-4c85-bc45-ae5ceb7485d6/download |
| id | rum_c2cd70ed3bb86b019c7eeec7ca76c865 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/15115 |
| 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:1822/15115 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Campos, Ana M. F. Oliveira Salaheldin, Abdellatif M. Paz, Filipe A. Almeida Rodrigues, Lígia M. |
| publishDate | 2011 |
| publisher.none.fl_str_mv | ARKAT USA, Inc. |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engARKAT USA, Inc.porThe reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles (3). Further reaction with aminoguanidine yielded 5´-cyanomeridianin analogues (4). The same intermediate reacted with p-methoxyphenylhydrazine to give the pyrazolyl derivative (8). Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate (3a) with hydroxylamine hydrochloride in basic medium afforded (5-amino-isoxazol-4-yl)-(1H-indol-3-yl)-methanone (5) and the acrylic acid derivative (6) after a short or a long heating, respectively. Unequivocal structural elucidation of the latter compound was achieved from single-crystal X-ray diffraction studies.application/pdfporSynthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitrilesCampos, Ana M. F. OliveiraSalaheldin, Abdellatif M.Paz, Filipe A. AlmeidaRodrigues, Lígia M.HostingInstitutionOrganizationalUniversidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptISSNIsPartOf1551-7012DOIIsPartOf10.3998/ark.5550190.0012.b112011-12-13T13:48:20Z2011-11-292011-11-29T00:00:00ZHandlehttps://hdl.handle.net/1822/15115http://purl.org/coar/access_right/c_abf2open accessIndoleAlkaloidsEnaminonitrileMeridianins3-Indolylazoles307452 bytesliteraturehttp://purl.org/coar/resource_type/c_6501journal articlehttp://purl.org/coar/access_right/c_abf2application/pdffulltexthttps://prod-dspace.uminho.pt/bitstreams/57b8aae0-9cba-4c85-bc45-ae5ceb7485d6/download |
| spellingShingle | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles Campos, Ana M. F. Oliveira Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| subject.fl_str_mv | Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| title | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| title_full | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| title_fullStr | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| title_full_unstemmed | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| title_short | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| title_sort | Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles |
| topic | Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| topic_facet | Indole Alkaloids Enaminonitrile Meridianins 3-Indolylazoles |
| url | https://hdl.handle.net/1822/15115 |
| visible | 1 |