Inserção de catalisador híbrido na síntese de beta-tiocetonas

Mariana Pompilio Darbem, Andrelson Wellington Rinaldi, Nelson Luis C. Domingues

Abstract


The Michael reaction (or Michael addition) involves the addition of a nucleophile, called Michael donor, to an electrophile (α,β-unsaturated), called Michael acceptor. Literature reports several types of nucleophiles applied in this reaction. Among them we can mention compounds containing a sulfur atom. When these nucleophiles are applied to this reaction, it is called as thia-Michael reaction. In this study thiophenol, p- chlorothiophenol and p-methoxythiophenol were tested as Michael donors, and several ketones and aldehydes as Michael acceptors, in order to obtain the formation of sigma bonds carbon-sulfur. Compounds that have in their structure the C-S bond are extremely important, because they can present, for example, antibiotic action, antimicrobial analgesic, and anti-HIV. This research proposes, besides the obtainment of  many beta-thioketonic compounds, the insertion of a new catalyst in thia-Michael reactions, the bis-L-zinc prolinate. This catalyst provided the obtainment of high yield compounds. The reactions were executed using ultrasound, which caused a significant decrease in the reaction time and an increase in the results obtained when compared with data obtained previously in literature. An important fact in this study is that the catalyst used is not soluble in the reaction media and it can be reused without abrupt loss of yield.


Keywords


alkylation; Mitsunobu system; pyrimidine; selectivity

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