In this manuscript we described the FeCl3/diorganyl diselenides promoted intramolecular cyclization of o-alkynyl anilines, as an alternative for the construction of functionalized 3-organoselenyl indoles. The cyclization reactions proceeded smoothly at room temperature in the presence of air giving the 3-organoselenyl indoles in good yields. Additionally, the 3-organoselenyl indoles proved to be quite useful as synthetic intermediates for the construction of more functionalized indole units through a selenium–lithium exchange reaction followed by trapping the lithium intermediate with different electrophiles.
The selective 6-endo-dig cyclization reaction of alkynyl aryl ketones with electrophilic organochalcogen species in the presence of Selectfluor® is described.
Organochalcogen-containing cyclic molecules have shown several promising pharmacological properties. Consequently, different strategies have been developed for their synthesis in the past few years. Particularly due to the low cost and environmental aspects, copper- and iron-promoted cyclization reactions of alkynyl substrates have been broadly and efficiently applied for this purpose. This short review presents an overview of the most recent advances in the synthesis of organochalcogen-containing carbo- and heterocycles by reacting diorganyl disulfides, diselenides, and ditellurides with alkyne derivatives in the presence of copper and iron salts to promote cyclization reactions.1 Introduction2 Synthesis of Carbo- and Heterocycles via Reactions of Alkynes with Diorganyl Dichalcogenides and Copper Salts3 Synthesis of Carbo- and Heterocycles via Reactions of Alkynes with Diorganyl Dichalcogenides and Iron Salts4 Conclusions
Rosmarinus officinalis (Lamiaceae family), also known as “alecrim,” is a perennial herb, typical of the Mediterranean region and widely distributed in Brazilian territory. Despite having demonstrated several properties of human interest, insecticide/larvicidal effect of essential oil from R. officinalis on insects remains unclear. In this study, we tested the effects of R. officinalis essential oil on biomarkers of oxidative damage in Drosophila melanogaster. Exposure to R. officinalis essential oil increased adult mortality and decreased geotaxis behavior in adult fruit flies. In addition, essential oil increased of larval mortality and impaired the developmental success in D. melanogaster. R. officinalis essential oil showed a significant repellent effect, with duration time of about 6 h. To understand the mechanism underlying the toxicity of essential oil both pro-oxidant effects and biomarkers of oxidative damage were evaluated in exposed flies. Exposure to essential oil caused a significant redox imbalance with impairment of both enzymatic and non-enzymatic antioxidant system and increased the lipid peroxidation levels. These results suggest that R. officinalis essential oil can be used as a bioinsecticide and/or larvicide as well as an alternative insect repellent.