Síntese de novos naftoimidazóis derivados de β-lapachona e compostos relacionados, empregando irradiação na região de microondas e reagentes suportados, e outras sínteses. / Synthsis of new naphthoimidazole derivatives from β-lapachona and related compounds, using irradiation on microwaves region and supported reagents, and other synthesis.

AUTOR(ES)

Ari Miranda da Silva

DATA DE PUBLICAÇÃO

2008

RESUMO

In this work it was investigeted the use of microwaves and supported reagents to the synthesis of β-lapachone, nor-β-apachone and β-lapachone-3-sulfonic acid naphthoimidazole derivatives. The purpose was to develop a methodology in agreement with the environmental exigencies, by the reduction of solvents use, more efficient energy transfer processes use of microwaves, with fastness and yelds improvments, choosing the apropriate conditions and supported reagents. Beyond of the synthesis of the naphthoimidazoles derivatives, to the most simple β-lapachone imidazole derivative (without substituint at the position 2 of the imidazole ring): a) it was investigated its resactivity toward eletrophilic aromatic substitution nitration, comparing the selectivity of diferent reactional systems (homogeneous and heterogeneous with supported reagents); b) it was investigated the tautomeric distribution of the products of nucleophilic substitution on the nitrogen atoms of the imidazolic ring methylation; and, c) it was investigated the reactivity of this compound toward dimerization reaction, which is possible to those imidazole systems with stabilization possibilities to the radicalar intermediaries species that are formed along the reaction. Some of the compounds prepaired were investigated about their inhibitory activity against the tripomatigote form of T.cruzi. Among them, the imidazolic derivative of β-lapachone with no substituint showed one of the better results found in this investigation.

ASSUNTO(S)

imidazole microondas nitração mivrowaves supported reagent -lapachona β reagente supotado -lapachone nitration quimica organica imidazol β

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