Abstract
Several fluorinated and trifluoromethylated indanone, tetralone and naphthone derivatives have been prepared via Claisen condensations and selective fluorinations in yields ranging from 22–60%. In addition, we report the synthesis of new, selectively fluorinated bindones in yields ranging from 72–92%. Of particular interest is the fluorination and trifluoroacetylation regiochemistry observed in these fluorinated products. We also note unusual transformations including a novel one pot, dual trifluoroacetylation, trifluoroacetylnaphthone synthesis via a deacetylation as well as an acetyl-trifluoroacetyl group exchange. Solid-state structural features exhibited by these compounds were investigated using crystallographic methods. Crystallographic results, supported by spectroscopic data, show that trifluoroacetylated ketones prefer a chelated cis-enol form whereas fluorinated bindone products exist primarily as the cross-conjugated triketo form.
Highlights
Molecules which have medicinal, industrial and herbicidal properties are of continued interest to the pharmaceutical, chemical and agrochemical communities
This solution is extracted with ether, and the organic layer dried over Na2SO4
The solvent is evaporated under reduced pressure and the crude diketone purified by radial chromatography
Summary
Industrial and herbicidal properties are of continued interest to the pharmaceutical, chemical and agrochemical communities. Since bioactivity is known to be enhanced in many classes of fluorinated molecules [3,7], it is desirous to prepare fluorine-containing molecules with similar architecture and gain a better understanding of their structure-property relationships. We reported the preparation and structure-property relationships of acyclic fluorinated and trifluoromethylated β-diketones, precursors to a variety of heterocyclic molecules [8,9,10]. While the syntheses and properties of these molecules have been investigated thoroughly, the preparation and study of selectively fluorinated, cyclic ketones containing the structural features of the molecules depicted in Figure 1 remains relatively limited [11]. 1.1 eq Selectfluor , MeCN, reflux, 10 h; ii. 1.1 eq Selectfluor®, MeCN, reflux, 16 h; v. 3.0 eq LDA, Et2O, 0 °C; (2) 2 eq CF3CO2Et, 0 °C→rt, 24 h; (3) 2 eq CF3CO2Et
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