Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction
Autor(a) principal: | |
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Data de Publicação: | 2012 |
Outros Autores: | |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFRGS |
Texto Completo: | http://hdl.handle.net/10183/104544 |
Resumo: | This work reports the functionalization of monoterpenoids with 2-iodo-1-methyl-1H-imidazole using Sonogashira crosscoupling reactions. Natural monoterpenes were also modified to obtain the corresponding alkynes which were used in the crosscoupling step. After a sequence of cross-coupling–hydrogenation– N-alkylation–ion metathesis, novel ionic liquids were obtained in reasonable yields. The obtained products can be used as scaffolds for the further synthesis of new ionic liquids derived from terpenoids and for new, potentially bioactive materials, e.g. polycyclic monocationic scaffolds. All obtained products show the characteristics of a room temperature ionic liquid (RTIL). |
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Speziali, Marcelo G.Monteiro, Adriano Lisboa2014-10-14T02:13:18Z20120039-7881http://hdl.handle.net/10183/104544000922777This work reports the functionalization of monoterpenoids with 2-iodo-1-methyl-1H-imidazole using Sonogashira crosscoupling reactions. Natural monoterpenes were also modified to obtain the corresponding alkynes which were used in the crosscoupling step. After a sequence of cross-coupling–hydrogenation– N-alkylation–ion metathesis, novel ionic liquids were obtained in reasonable yields. The obtained products can be used as scaffolds for the further synthesis of new ionic liquids derived from terpenoids and for new, potentially bioactive materials, e.g. polycyclic monocationic scaffolds. All obtained products show the characteristics of a room temperature ionic liquid (RTIL).application/pdfengSynthesis : journal of synthetic organic chemistry. Vol. 44, no. 22 (2012), p. 3505-3511TerpenóidesPaládioLíquidos iônicosCatáliseTerpenoidsCross-couplingPalladiumIonic liquidsCatalysisSynthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reactionEstrangeiroinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFRGSinstname:Universidade Federal do Rio Grande do Sul (UFRGS)instacron:UFRGSORIGINAL000922777.pdf000922777.pdfTexto completo (inglês)application/pdf215116http://www.lume.ufrgs.br/bitstream/10183/104544/1/000922777.pdf7accacb356ed7da68e2fdb08c97b3be5MD51TEXT000922777.pdf.txt000922777.pdf.txtExtracted Texttext/plain33949http://www.lume.ufrgs.br/bitstream/10183/104544/2/000922777.pdf.txtdd6ccd902cc128253add9cef6ac7c91eMD52THUMBNAIL000922777.pdf.jpg000922777.pdf.jpgGenerated Thumbnailimage/jpeg2299http://www.lume.ufrgs.br/bitstream/10183/104544/3/000922777.pdf.jpgb79e5c89c0d54ad47cf7e71363ff3f3cMD5310183/1045442018-10-10 08:00:41.012oai:www.lume.ufrgs.br:10183/104544Repositório de PublicaçõesPUBhttps://lume.ufrgs.br/oai/requestopendoar:2018-10-10T11:00:41Repositório Institucional da UFRGS - Universidade Federal do Rio Grande do Sul (UFRGS)false |
dc.title.pt_BR.fl_str_mv |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
title |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
spellingShingle |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction Speziali, Marcelo G. Terpenóides Paládio Líquidos iônicos Catálise Terpenoids Cross-coupling Palladium Ionic liquids Catalysis |
title_short |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
title_full |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
title_fullStr |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
title_full_unstemmed |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
title_sort |
Synthesis of imidazole-derived ionic liquids from monoterpenes by means of the sonogashira reaction |
author |
Speziali, Marcelo G. |
author_facet |
Speziali, Marcelo G. Monteiro, Adriano Lisboa |
author_role |
author |
author2 |
Monteiro, Adriano Lisboa |
author2_role |
author |
dc.contributor.author.fl_str_mv |
Speziali, Marcelo G. Monteiro, Adriano Lisboa |
dc.subject.por.fl_str_mv |
Terpenóides Paládio Líquidos iônicos Catálise |
topic |
Terpenóides Paládio Líquidos iônicos Catálise Terpenoids Cross-coupling Palladium Ionic liquids Catalysis |
dc.subject.eng.fl_str_mv |
Terpenoids Cross-coupling Palladium Ionic liquids Catalysis |
description |
This work reports the functionalization of monoterpenoids with 2-iodo-1-methyl-1H-imidazole using Sonogashira crosscoupling reactions. Natural monoterpenes were also modified to obtain the corresponding alkynes which were used in the crosscoupling step. After a sequence of cross-coupling–hydrogenation– N-alkylation–ion metathesis, novel ionic liquids were obtained in reasonable yields. The obtained products can be used as scaffolds for the further synthesis of new ionic liquids derived from terpenoids and for new, potentially bioactive materials, e.g. polycyclic monocationic scaffolds. All obtained products show the characteristics of a room temperature ionic liquid (RTIL). |
publishDate |
2012 |
dc.date.issued.fl_str_mv |
2012 |
dc.date.accessioned.fl_str_mv |
2014-10-14T02:13:18Z |
dc.type.driver.fl_str_mv |
Estrangeiro info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://hdl.handle.net/10183/104544 |
dc.identifier.issn.pt_BR.fl_str_mv |
0039-7881 |
dc.identifier.nrb.pt_BR.fl_str_mv |
000922777 |
identifier_str_mv |
0039-7881 000922777 |
url |
http://hdl.handle.net/10183/104544 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.ispartof.pt_BR.fl_str_mv |
Synthesis : journal of synthetic organic chemistry. Vol. 44, no. 22 (2012), p. 3505-3511 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
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Repositório Institucional da UFRGS |
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