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Previous issue date: 2015-07-23 / Coordena??o de Aperfei?oamento de Pessoal de N?vel Superior (CAPES) / A s?ntese de compostos heteroc?clicos, tais como derivados de quinoxalina, tem se mostrado
bastante relevante e promissora devido ?s diversas aplica??es verificadas nas ?reas biol?gicas
e tecnol?gicas. Este trabalho dedicou-se a s?ntese, caracteriza??o e reatividade de derivados
quinoxal?nicos a partir de dois precursores sint?ticos: o ?cido-L-asc?rbico (1) e do bloco de
constru??o 2,3-dicloro-6,7-dinitroquinoxalina (2). A partir da s?ntese e caracteriza??o dos
compostos derivados do ?cido-L-asc?rbico (1) foram realizados estudos visando sua aplica??o
como quimiossensores, no qual o composto 36 demonstrou-se seletivo para o ?on Cu2+, em
metanol, mediante an?lises colorim?trica e por espectroscopia UV-vis?vel. Al?m disto, an?lises
iniciais sugerem que o composto 39 derivado de 36, uma base de Schiff, tamb?m apresenta
caracter?sticas de quimiossensor para o mesmo metal. A partir do composto 2, foram
sintetizados cinco compostos atrav?s de rea??es de substitui??o nucleof?lica arom?tica com
aminas alif?ticas. O controle das condi??es experimentais permitiu a obten??o tanto de produtos
mono- quanto dissubstitu?dos. Estudos de reatividade foram realizados com dois prop?sitos: i)
investigar a possibilidade de atua??o do composto 47 como quimiossensor para ?nions, a partir
da rea??o com hidr?xido de s?dio em DMSO, atrav?s dos resultados obtidos pela an?lise de
imagem e espectroscopia UV-vis?vel; ii) caracterizar cineticamente a convers?o do composto
44 em 46 atrav?s da an?lise de imagens pelos m?todos RGB e multivariada a partir de dados de
CCD, mostrando-se uma ferramenta simples e de baixo custo para an?lises qualitativas e
quantitativas. / Synthesis of heterocyclic compounds, as quinoxaline derivatives, has being shown to be
relevant and promissor due to expressive applications in biological and technological areas.
This work was dedicated to the synthesis, characterization and reactivity of quinoxaline
derivatives in order to obtain new chemosensors. (L)-Ascorbic acid (1) and 2,3-dichloro-6,7-
dinitroquinoxalina (2) were explored as synthetic precursors. Starting from synthesis of 1 and
characterization of compounds derived from (L)-ascorbic acid, studies were performed
investigating the application of products as chemosensors, in which compound 36 demonstrated
selective affinity for Cu2+ ?ons in methanolic solution, by naked-eye (colorimetric) and UVvisible
analyses. Further, initial analysis suggests that 39 a Schiff?s base derived from 36 also
presents this feature. Five quinoxaline derivatives were synthesized from building block 2
through nucleophilic aromatic substitution by aliphatic amines, in which controlling the
experimental conditions allows to obtain both mono- and di-substituted derivatives. Reactivity
studies were carried out with two purposes: i) investigate the possibility of 47 compound being
a chemosensor for anion, based on its interaction with sodium hydroxide in DMSO, using image
analysis and UV-visible spectroscopy; ii) characterize kinetically the conversion of compound
44 into 46 based on RGB and multivariate image analysis from TLC data, as a simple and
inexpensive qualitative and quantitative tool.
| Identifer | oai:union.ndltd.org:IBICT/oai:repositorio.ufrn.br:123456789/20286 |
| Date | 23 July 2015 |
| Creators | Silva, Lilian Cavalcante da |
| Contributors | 03114939988, http://lattes.cnpq.br/2848745987784319, Cavalcanti, Livia Nunes, 03977264494, http://lattes.cnpq.br/4902766144157822, Cristiano, Rodrigo, 02389345948, http://lattes.cnpq.br/3258880863999415, Ara?jo, Renata Mendon?a, Menezes, Fabricio Gava |
| Publisher | Universidade Federal do Rio Grande do Norte, PROGRAMA DE P?S-GRADUA??O EM QU?MICA, UFRN, Brasil |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Source | reponame:Repositório Institucional da UFRN, instname:Universidade Federal do Rio Grande do Norte, instacron:UFRN |
| Rights | info:eu-repo/semantics/openAccess |
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