Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol

Detalhes bibliográficos
Autor(a) principal: Axundova, F. N.
Data de Publicação: 2019
Outros Autores: Kurbanova, M. M., Huseynzada, A. E., Alves, Maria José Chão
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/73062
Resumo: (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol was synthesized in two steps by the Diels-Alder reaction of penta-2,4-dien-1-ol with diethyl azodicarboxylate in the presence of (S)-BINOL as chiral catalyst. The subsequent Boc-protection of the 2-position of the pyridazine ring, ring-closing carbonylation of the hydroxy group, and deprotection afforded a bicyclic iminosugar analog. The structure of the isolated compounds was proved by NMR, IR, and mass spectra and elemental analyses.
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spelling Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol1-azafagomineBoc protectionDiels-Alder reactionimino sugarspyridazineS-BINOLCiências Naturais::Ciências QuímicasScience & Technology(S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol was synthesized in two steps by the Diels-Alder reaction of penta-2,4-dien-1-ol with diethyl azodicarboxylate in the presence of (S)-BINOL as chiral catalyst. The subsequent Boc-protection of the 2-position of the pyridazine ring, ring-closing carbonylation of the hydroxy group, and deprotection afforded a bicyclic iminosugar analog. The structure of the isolated compounds was proved by NMR, IR, and mass spectra and elemental analyses.Pleiades PublishingUniversidade do MinhoAxundova, F. N.Kurbanova, M. M.Huseynzada, A. E.Alves, Maria José Chão20192019-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/73062engAxundova, F.N., Kurbanova, M.M., Huseynzada, A.E. et al. Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol. Russ J Org Chem 55, 1975–1978 (2019). https://doi.org/10.1134/S10704280191202971070-428010.1134/S1070428019120297https://link.springer.com/article/10.1134%2FS1070428019120297info: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:RCAAP2023-07-21T12:34:51Zoai:repositorium.sdum.uminho.pt:1822/73062Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:30:36.507231Repositório 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 New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
title Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
spellingShingle Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
Axundova, F. N.
1-azafagomine
Boc protection
Diels-Alder reaction
imino sugars
pyridazine
S-BINOL
Ciências Naturais::Ciências Químicas
Science & Technology
title_short Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
title_full Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
title_fullStr Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
title_full_unstemmed Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
title_sort Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol
author Axundova, F. N.
author_facet Axundova, F. N.
Kurbanova, M. M.
Huseynzada, A. E.
Alves, Maria José Chão
author_role author
author2 Kurbanova, M. M.
Huseynzada, A. E.
Alves, Maria José Chão
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Axundova, F. N.
Kurbanova, M. M.
Huseynzada, A. E.
Alves, Maria José Chão
dc.subject.por.fl_str_mv 1-azafagomine
Boc protection
Diels-Alder reaction
imino sugars
pyridazine
S-BINOL
Ciências Naturais::Ciências Químicas
Science & Technology
topic 1-azafagomine
Boc protection
Diels-Alder reaction
imino sugars
pyridazine
S-BINOL
Ciências Naturais::Ciências Químicas
Science & Technology
description (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol was synthesized in two steps by the Diels-Alder reaction of penta-2,4-dien-1-ol with diethyl azodicarboxylate in the presence of (S)-BINOL as chiral catalyst. The subsequent Boc-protection of the 2-position of the pyridazine ring, ring-closing carbonylation of the hydroxy group, and deprotection afforded a bicyclic iminosugar analog. The structure of the isolated compounds was proved by NMR, IR, and mass spectra and elemental analyses.
publishDate 2019
dc.date.none.fl_str_mv 2019
2019-01-01T00:00:00Z
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/1822/73062
url http://hdl.handle.net/1822/73062
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Axundova, F.N., Kurbanova, M.M., Huseynzada, A.E. et al. Synthesis of New Iminosugar Derivatives Based on (S)-(1,2,3,6-Tetrahydropyridazin-3-yl)methanol. Russ J Org Chem 55, 1975–1978 (2019). https://doi.org/10.1134/S1070428019120297
1070-4280
10.1134/S1070428019120297
https://link.springer.com/article/10.1134%2FS1070428019120297
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 Pleiades Publishing
publisher.none.fl_str_mv Pleiades Publishing
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
_version_ 1799132810869473280

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