Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers.

Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group with the OCF functionality. The scope of our method includes 31 examples of ring-substituted anilines, including amides and sulfonamides.

Synthesis and characterization of two homologous series of diastereomeric 2-alkoxyphenylcarbamates.

Two homologous series of racemic diastereomeric cis- and trans-(2-dimethylaminomethylcycloheptyl)-2-alkoxyphenylcarbamates with alkyl chain lengths ranging from C₁ to C₈ were synthesized by stereoselective reactions. The chemical structures of these compounds were confirmed by ¹H-NMR, ¹³C-NMR and IR spectroscopy and their physico-chemical properties were characterized. The two new series of diastereomeric compounds were tested for their local anesthetic activity and parabolic relationship between the local anesthetic activity and lipophilicity was found for both cis- and trans-series.