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Mémoire de Maîtrise
DOI
10.11606/D.9.2013.tde-16012014-141941
Document
Auteur
Nom complet
Stanley Nunes Siqueira Vasconcelos
Adresse Mail
Unité de l'USP
Domain de Connaissance
Date de Soutenance
Editeur
São Paulo, 2013
Directeur
Jury
Stefani, Helio Alexandre (Président)
Ando, Rômulo Augusto
Santos, Alcindo Aparecido dos
Titre en portugais
Síntese de 5-organoteluro-1H-1,2,3-triazóis-1,4-dissubstituídos, funcionalização via reação de acoplamento cruzado de Sonogashira e síntese one-pot de derivados do indol-3-glioxila e indol-3-glioxil-1,2,3-triazóis
Mots-clés en portugais
Alquinos
Click Chemistry
Indol
Reações Multicomponente (MCRs)
Sonogashira
Telurio
Triazol
Resumé en portugais
No capítulo 1 apresentamos uma síntese eficiente de compostos 5-organoteluro-1H- 1,2,3-triazóis realizada via reação de cicloadição [3+2] entre azidas orgânicas e alquinos substituídos com organotelúrio. Além disso, os 5-organoteluro-1H-1,2,3-triazóis foram funcionalizados na posição 5 do anel triazólico por reação de acoplamento cruzado de Sonogashira. A regioquímica dos produtos de cicloadição foram descritas com base em experimentos de RMN, cálculos teóricos e cristalografia de raio-x. Apresentamos uma proposta mecanística para a cicloadição mediada por cobre, baseada em experimentos de espectrometria de massas de alta resolução. No capítulo 2, investigamos a eficiência de reações one-pot com indol, cloreto de oxalila e diferentes nucleófilos para obtermos derivados do indol-3-glioxila em condições adequadas. Do mesmo modo, envolvendo a adição de azidas orgânicas, levando à síntese de indol-3-glioxil-1,2,3-triazóis, os produtos foram obtidos com rendimentos que variaram de 59 a 85%.
Titre en anglais
Synthesis of 5-organoteluro-1,4-disubstituted-1H-1,2,3- triazoles, functionalization via Sonogashira cross-coupling reaction and synthesis one-pot of indole-3-glyoxyl derivatives and indole-3-glyoxyl triazoles
Mots-clés en anglais
Alkynes
Click Chemistry
Indole
Multicomponent reactions (MCRs)
Sonogashira
Tellurium
Triazole
Resumé en anglais
In chapter 1 we present an efficient synthesis of 5-organotelluro-1H-1,2,3-triazole compounds that was accomplished via the [3+2]-cycloaddition reaction of organoazides and organotelluro alkynes. Additionally, 5-organotelluro-1H-1,2,3-triazoles were readily functionalized at the 5-position via the Sonogashira cross-coupling reaction, leading to highly functionalised triazoles. The regiochemistry of the products was assessed by bidimensional NMR experiments, theoretical calculations and x-ray crystallography. We presented a mechanistic proposal for the cycloaddition mediated by copper, based on high resolution mass spectrometry experiments. In chapter 2 we investigated a general and efficient reaction of indole with oxalyl chloride and nucleophiles providing indole-3-glyoxyl derivatives which has been developed in mild conditions. In the same fashion, the other reaction involved the addition of organic azides leading to the synthesis of indole-3-glyoxyl-1,2,3-triazoles, which proceeds smoothly generating the products in moderate to high yields.
 
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Date de Publication
2014-04-01
 
AVERTISSEMENT: Le matériau se réfère à des documents provenant de cette thèse ou mémoire. Le contenu de ces documents est la responsabilité de l'auteur de la thèse ou mémoire.
  • Stefani, Helio A., et al. Functionalization of 5-Telluro-1,2,3-triazoles via Te-Li Transmetallation Exchange. European Journal of Organic Chemistry , 2013.
  • Stefani, Hélio A., et al. Functionalization of 5-telluro-1,2,3-triazoles: Te/Li exchange and Suzuki-Miyaura cross-coupling reaction [doi:10.1016/j.tetlet.2013.03.061]. Tetrahedron Letters [online], 2013, vol. 54, p. 2809-2812.
  • Stefani, Hélio A., et al. One-pot three-component synthesis of indole-3-glyoxyl derivatives and indole-3-glyoxyl triazoles [doi:10.1016/j.tetlet.2013.08.064]. Tetrahedron Letters [online], 2013, vol. 54, p. 5821-5825.
  • Stefani, Hélio A., et al. Synthesis of 5-Organotellanyl-1 H -1,2,3-triazoles: Functionalization of the 5-Position Scaffold by the Sonogashira Cross-Coupling Reaction [doi:10.1002/ejoc.201300009]. European Journal of Organic Chemistry [online], 2013, vol. 5, p. n/a-n/a.
  • Zukerman-Schpector, Julio, et al. 3-Ethenyl-1-(4-methylphenylsulfonyl)-1 H -indole [doi:10.1107/s1600536812021526]. Acta Crystallographica. Section E [online], 2012, vol. 68, p. o1829-o1830.
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Centro de Informática de São Carlos
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