Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles

Detalhes bibliográficos
Autor(a) principal: Campos, Ana M. F. Oliveira
Data de Publicação: 2011
Outros Autores: Salaheldin, Abdellatif M., Paz, Filipe A. Almeida, Rodrigues, Lígia M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/15115
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.
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spelling Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitrilesIndoleAlkaloidsEnaminonitrileMeridianins3-IndolylazolesScience & TechnologyThe 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.Fundação para a Ciência e a Tecnologia (FCT) - SFRH/BPD/31490/2006FEDER - REEQ/ 630/QUI/2005ARKAT USA, Inc.Universidade do MinhoCampos, Ana M. F. OliveiraSalaheldin, Abdellatif M.Paz, Filipe A. AlmeidaRodrigues, Lígia M.2011-11-292011-11-29T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/15115eng1551-701210.3998/ark.5550190.0012.b11http://www.arkat-usa.org/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:RCAAP2024-05-11T04:35:32Zoai:repositorium.sdum.uminho.pt:1822/15115Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-11T04:35:32Repositório 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 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
title Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
spellingShingle Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
Campos, Ana M. F. Oliveira
Indole
Alkaloids
Enaminonitrile
Meridianins
3-Indolylazoles
Science & Technology
title_short 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_sort Synthesis of 3-indolylazoles and meridianin derivatives from indolyl enaminonitriles
author Campos, Ana M. F. Oliveira
author_facet Campos, Ana M. F. Oliveira
Salaheldin, Abdellatif M.
Paz, Filipe A. Almeida
Rodrigues, Lígia M.
author_role author
author2 Salaheldin, Abdellatif M.
Paz, Filipe A. Almeida
Rodrigues, Lígia M.
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Campos, Ana M. F. Oliveira
Salaheldin, Abdellatif M.
Paz, Filipe A. Almeida
Rodrigues, Lígia M.
dc.subject.por.fl_str_mv Indole
Alkaloids
Enaminonitrile
Meridianins
3-Indolylazoles
Science & Technology
topic Indole
Alkaloids
Enaminonitrile
Meridianins
3-Indolylazoles
Science & Technology
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.
publishDate 2011
dc.date.none.fl_str_mv 2011-11-29
2011-11-29T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/1822/15115
url http://hdl.handle.net/1822/15115
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1551-7012
10.3998/ark.5550190.0012.b11
http://www.arkat-usa.org/
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv ARKAT USA, Inc.
publisher.none.fl_str_mv ARKAT USA, Inc.
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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