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Master's Dissertation
DOI
10.11606/D.9.2012.tde-07032013-094439
Document
Author
Full name
Hugo Antonio Canduzini
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2012
Supervisor
Committee
Stefani, Helio Alexandre (President)
Santos, Alcindo Aparecido dos
Vieira, Adriano Siqueira
Title in Portuguese
Síntese e funcionalização de 1,2,3-triazóis via reação de cicloadição [3+2] de azidas e acetilenos terminais
Keywords in Portuguese
1-2- 3-Triazol
Bis-triazol
Click-chemistry
Insumos farmacêuticos
Abstract in Portuguese
O objetivo deste trabalho é explorar a síntese e funcionalização de 1,2,3- triazóis empregando o uso de reações do tipo "Click-chemistry", que é uma abordagem para a síntese de diversos compostos com base em reações de formação de ligação carbono-heteroátomo, onde a reação é estereoespecífica, altamente eficiente e geralmente com elevados rendimentos e em alguns casos ausência de subprodutos. O composto 1,2,3-triazol, sendo o material de partida para a continuidade do projeto foi preparado a partir do álcool propargílico (4) em presença de uma azida orgânica (1) e utilizando cobre(I) como agente promotor. Após a obtenção de uma série de compostos 1,2,3-triazólicos (2), procedeu-se a etapa de tosilação da hidroxila e posterior cicloadição multicomponente de um novo 1,2,3-triazol formando compostos bis-triazólicos. Os bis-triazóis (5) obtidos foram testados frente a cepas fúngicas, responsáveis por dermatites, com resultados satisfatórios. Ainda essas estruturas poderão ser empregados como blocos construtores para a síntese de estruturas mais complexas.
Title in English
Synthesis and functionalization of 1,2,3-triazoles via cycloaddition [3 +2] azide in the presence of acetylenes
Keywords in English
1-2-3-Triazole
Bis-triazole
Click-chemistry
Pharmaceutical raw material
Abstract in English
The aim of this work has been exploring the synthesis and functionalization of 1,2,3-triazoles employing the use of "click-chemistry" concept, which is defined as an approach for synthesis of various compounds based on reactions of carbon-heteroatom bond formation, which the reaction is stereospecific, high-efficiently, commonly gives high yields and in some cases no by-products are formed. The compound 1,2,3-triazole, which is the main starting material for the next steps was prepared from propargyl alcohol (4) in the presence of an organic azide (1) and copper(I) as a reaction promoter. Subsequently with a series of 1,2,3-triazole (2n) prepared we proceeded to the next step which is the substitution of hydroxyl for a tosyl group and after that a multicomponent cycloaddition of a new 1,2,3-triazole compound forming bis-triazoles. Bis-triazoles (5) were tested against fungal strains, responsible for dermatitis, with delighted results, furhtermore this class of strutures can be used as building blocks to improve efficiency in some other more complex structure.
 
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Publishing Date
2013-04-01
 
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, Hélio A., Canduzini, Hugo A., and Manarin, Flávia. Modular synthesis of mono, di, and tri-1,4-disubstituted-1,2,3-triazoles through copper-mediated alkyne azide cycloaddition [doi:10.1016/j.tetlet.2011.09.004]. Tetrahedron Letters [online], 2011, vol. 52, p. 6086-6090.
  • Manarin, Flávia, CANDUZINI, H. A., e STEFANI, H. A. Synthesis and functionalization of 1,2,3-triazoles via cycloaddition [3 +2] azide in the presence of acetylenes. In 14th Brazilian Meeting on Organic Synthesis, Brasília, 2011. Synthesis and functionalization of 1,2,3-triazoles via cycloaddition [3 +2] azide in the presence of acetylenes., 2011. Resumo.
All rights of the thesis/dissertation are from the authors
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