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Campo DC | Valor | Idioma |
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dc.creator | Nascimento, Wilson Silva do | - |
dc.creator | Silva, Mauro Gomes da | - |
dc.creator | Oliveira, Ronaldo Nascimento de | - |
dc.creator | Câmara, Celso Amorim | - |
dc.date.accessioned | 2022-10-24T13:47:17Z | - |
dc.date.available | 2022-10-24T13:47:17Z | - |
dc.date.issued | 2010-03 | - |
dc.identifier.issn | 1984-6428 | pt_BR |
dc.identifier.uri | https://repositorio.ufms.br/handle/123456789/5305 | - |
dc.description.abstract | Naphthoquinones are known according to their important bio-activities, such as their antitumoral and topoisomerase inhibition properties. From 2-azido (3) or 2,3- diacetylene-1,4-naphthoquinone (4) it was possible to obtain triazole derivatives (naphthoquinonic). This work describes the synthesis of two novel molecules, with triazole groups linked to 1,4-naphthoquinone using the 1,3-dipolar cycloaddition and Sonogashira reactions. The synthetic strategy followed two routes (Scheme 1). First, we synthesized the 2-bromo-1,4-naphthoquinone (2, yield 98%) by using Br2 and CH3CO2H, and then used it to obtain 2-azido-1,4-naphthoquinone (3, yield 62%) from compound 1, along with ethanolic solution (reflux) and NaN3. Finally, we prepared 1,2,3-triazole compounds (4a, b) by 1,3-dipolar cycloaddition, involving compound (3) and terminal acetylenes (phenylacetylene, a) and glycoside (b) using Cu(OAc)2 and ascorbate, under argon atmosphere. During the second step, 2,3-dibromo-1,4-naphthoquinone was prepared using Br2/CH2Cl2 at room temperature. From compound (5) it was possible to synthesize (6), catalyzed by Pd(PPh3)2Cl2/CuI/Et3N, under argon atmosphere, in 40% yield. The 1,3-dipolar cycloaddition reactions involving 2-azido-1,4-naphthoquinone (3) and alkynes (a, yield 23% and b, yield 30%) were conducted using the solvent system, (1:1) terc-BuOH/H2O/r.t/ 20 mol% of Cu(OAc)2 and sodium ascorbate, under stirring during 24 hours. The reaction involving 2,3-dibromo-1,4-naphthoquinone (5, yield 65%) and phenylacetylene was prepared using the solvent mixture (2:1) DMSO/CHCl3 and catalytic amount of CuI/Pd(PPh3)2Cl2. The final products were characterized by elemental analysis and spectrometric techniques (IR, NMR 1H and 13C). Two novel triazole compounds were synthesized from naphthoquinones by 1,3-dipolar cycloaddition from suitable 1,4-naphthoquinones obtained by Sonogashira couplings. | pt_BR |
dc.language | eng | pt_BR |
dc.publisher | Fundação Universidade Federal de Mato Grosso do Sul | pt_BR |
dc.relation.ispartof | Orbital: The Electronic Journal of Chemistry | pt_BR |
dc.rights | Acesso Aberto | pt_BR |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Brazil | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/br/ | * |
dc.subject | Naftoquinonas | pt_BR |
dc.subject | Reação de Cicloadição | pt_BR |
dc.subject | Reações Químicas | pt_BR |
dc.subject | Cycloaddition Reaction | pt_BR |
dc.subject | Naphthoquinones | pt_BR |
dc.subject | Chemical Reactions | pt_BR |
dc.title | Synthesis of 1,4-naphthoquinone derivatives using 1,3-dipolar cycloaddition and Sonogashira reactions | pt_BR |
dc.type | Resumo | pt_BR |
dc.citation.volume | 2 | pt_BR |
dc.citation.issue | Suppl. 1 | pt_BR |
dc.publisher.country | Brasil | pt_BR |
dc.publisher.initials | UFMS | pt_BR |
dc.subject.cnpq | CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA | pt_BR |
Aparece nas coleções: | Orbital: The Electronic Journal of Chemistry |
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Synthesis of 1,4-naphthoquinone derivatives using 1,3-dipolar cycloaddition and Sonogashira reactions.pdf | 407,24 kB | Adobe PDF | Visualizar/Abrir |
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