Estudo das reações de 5-bromo-1,1,1-trifluor-4-metoxipent-3-en-2-ona com aminoácidos

Abstract

The present work describe the reactions using 5-bromo-1,1,1-trifluoro-4-metoxipent-3-en-2-ona, on its free and esterified form. Such reactions aim to have new compounds derive from 4-amino-5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one, 1,4-Oxazinas and substituted 2,4-disubstituted pyrroles. First of all, all the initial material was synthesized. An acylation reaction was performed with 2-methoxipropen with trifluoroacetic anhydride, resulting in 1,1,1-trifluoro-4-metoxipent-3-en-2-one, which it has been converted through a bromination reaction to 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one. Next, the synthesis of enaminones — 2-methyl-((1-bromo-5,5,5-trifluoro-4-oxopent-2-en-2-yl)amino)acetate and 2-methyl-((1-bromo-5,5,5-trifluoro-4-oxopent-2-en-2-yl)amino)propanoate — with the esterified glicine and alanine, was performed. We envisioned that the 2-methyl-((1-bromo-5,5,5-trifluoro-4-oxopent-2-en-2-yl)amino)acetate could be a suitable starting material for obtaining pyrroles derived of amino acids such as methyl 2-((5-trifluoromethyl)-1H-1pyrrol-3-il) amine) acetate. Additionally, a series of compounds such as 5-(3,3,3-trifluoro-2-oxopropylidene)morpholin-2-one, 3-methyl-5-(3,3,3-trifluoro-2-oxopropylidene) morpholin-2-one, 3-benzyl-5-(3,3,3-trifluoro-2-oxopropylidene)morpholin-2-one and 3-(sec-butyl)-5-(3,3,3-trifluoro-2-oxopropylidene)morpholin-2-one, were obtained from the reaction of the 5-bromo-1,1,1-trifluor-4-metoxipent-3-em-2-ona with amino acids in the free form.