Sintese e caracterização de novas quinazolinas polissubstituidas
AUTOR(ES)
Luis Fernando Cabeça
DATA DE PUBLICAÇÃO
2004
RESUMO
The objective of the present work was to synthesize new polisubstituted quinazolines from new aminocarboxylic acids. The first synthetic route, using 3,4-diidroxybenzoic acid and 4-methylcatechol, did not lead to satisfactory results. Therefore, a new route was proposed from 6-nitropiperonal, bearing a different protecting group - methylenedioxy. This new route, involving just two steps gave 2-amino-4,5-methylenedioxy-benzoic acid. Literature procedures were used for the reaction of the 2-amino-4,5methylenedioxy-benzoic acid with formamidine acetate to give 6,7 -methylenedioxy-4quinazolone. The second step involved the conversion of the quinazolone to 6,7methylenedioxy-4-chloroquinazoline, by the reaction with SOCl2 containing a catalytic amount of DMF. The next step, was the reaction of aromatic nucleofilic substitution of chloro from the chloroquinazoline by the corresponding 3-substituted anilines (R = H, Sr, OCH3, CH3, N(CH3)2, in presence of isopropanol, under reflux. This reaction gave the desired 4-N-(3 -substituted-phenyl)amino-6, 7 -methylenedioxyquinazolines. These compounds were characterized by H and C NMR, and IR spectroscopy, and mass spectrometry. Complementary data were obtained form elemental analyses and for the full assignment of H and C NMR chemical shifts some 2D techniques such as gCOSY, HSQC and gHMSC were employed.
ASSUNTO(S)
ACESSO AO ARTIGO
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