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Master's Dissertation
DOI
10.11606/D.9.2013.tde-16012014-141941
Document
Author
Full name
Stanley Nunes Siqueira Vasconcelos
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2013
Supervisor
Committee
Stefani, Helio Alexandre (President)
Ando, Rômulo Augusto
Santos, Alcindo Aparecido dos
Title in Portuguese
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
Keywords in Portuguese
Alquinos
Click Chemistry
Indol
Reações Multicomponente (MCRs)
Sonogashira
Telurio
Triazol
Abstract in Portuguese
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%.
Title in English
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
Keywords in English
Alkynes
Click Chemistry
Indole
Multicomponent reactions (MCRs)
Sonogashira
Tellurium
Triazole
Abstract in English
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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Publishing Date
2014-04-01
 
WARNING: The material described below relates to works resulting from this thesis or dissertation. The contents of these works are the author's responsibility.
  • 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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