A Novel Approach to C-Trimethylsilyl-1,3-azoles

Abstract

Direct silylation of 1,3-azoles with bromotrimethylsilane in the presence of triethylamine was investigated. 5-Phenyloxazole, benzoxazole, 1-methyl-1,2,4-triazole, 2-aryl-1,3,4-oxa-and thiadiazoles were found to give the corresponding 2-or 5-trimethylsilyl derivatives.

In Situ Generation and Trapping of Aryllithium and Arylpotassium Species by Halogen, Sulfur, and Carbon Electrophiles

“…Presumably, N-acylation is followed by deprotonation of the acidic C-2 proton and subsequent acyl migration affords the final product. Silylations under similar conditions have also been successful 5. Finally, Kondo has shown that electron-rich and electron-deficient arenes can be functionalized by employing t Bu-P4 base/non-enolizable ketone and aldehyde mixtures 6…”

C‐Silyl‐N,N‐dialkyl‐N′‐arylformamidines: Synthesis and Reactions with Phosphorus(III) Chlorides

“…Thus, the attempt to synthesize N ‐silyltriazolylidenes from the corresponding N ‐silyltriazolium salts led to C ‐silyltriazoles , . The reaction of bromotrimethylsilane with a set of nitrogen‐containing heterocycles directly led to C ‐silylated derivatives, which were most likely formed by the carbene mechanism . C ‐Silylformamidines 3 are colorless, crystalline compounds that are extremely moisture‐sensitive.…”

Easily Vaporizable Ionic Liquids – No Contradiction!

“…N-Methyl-NЈ-trimethylsilylimidazolium Bromide (1; MTMSImBr): [45] N-Methylimidazole (17.9 g, 0.2 mol) was slowly added dropwise to a solution of bromotrimethylsilane (33.4 g, 0.2 mol) in dry diethyl ether (100 mL) under Ar at 0°C. The resulting white precipitate was filtered off washed thoroughly with diethyl ether and finally dried in vacuo at ambient temperature.…”