1-Hydroxyimidazole Derivatives III.^1,2Synthesis of 1-Alkyloxy-, 1-Arylalkyloxy-, and 1-Phenoxy-1H-imidazoles

Crystal Structures of 1-Hydroxyimidazole and Its Salts

“…1-Hydroxyimidazole (1) [45376-79-2] was synthesized as described [7]. Single crystals were obtained from anhydrous acetone under an argon atmosphere.…”

“…The first attempts ended up with benzyloxy or imidazolinone derivatives, stopping just short of the desired target [5,6]. Considerable time has now passed by since the first practical synthesis of 1-hydroxyimidazole has been reported, involving selective hydrogenation of 1,3-dihydroxyimidazolium chloride [7]. Other syntheses of this compound have been published in the meantime.…”

Hydroxy-1H-imidazole-3-oxides – Synthesis, Kinetic Acidity, and Application in Catalysis and Supramolecular Anion Recognition

“…Surprisingly, very little is known about compounds 1 with heteroatoms (O, N, S) directly attached to the ring nitrogen atoms, e. g. R 1 , R 3 = OR, NHR, or Scheme 2. NR 2 . Only limited accounts on formal imidazolium N-oxide derivatives [5], N, N -dialkoxy imidazolium salts [6], alkylamino [7], or N, N -bis(alkylamino) imidazolium derivatives [8] are available. Recent work of Schottenberger and colleagues attracted our attention because of our own interest in basic properties of imidazolium salts such as kinetic acidity [9] and their use as anion receptors [10] or precatalysts in aqueous Suzuki coupling reactions [11].…”

“…They reported on the synthesis, ionic liquid behavior and use of simple N, N -dialkoxy imidazolium salts as NHC precursors [12]. Inspecting the experimental NMR data of dimethoxy and diethoxy imidazolium salts revealed a difference in the C 2 -H proton resonance of about 0.1 ppm by exchanging the counterion from e. g. PF 6 − to bromide [12a]. Therefore, we decided to check whether these novel imidazolium salts are useful for our application in supramolecular chemistry and catalysis.…”

Thermal rearrangement of an N-hydroxy-imidazole thiocarbamoyl derivative as a simple entry into the 4-thio-imidazole motif

“…The actual synthesis of compound 1 (Z = NMe 2 ) is shown in Scheme 2, where for the steps leading to 3 literature procedures were used. 7,8 The appropriate thiocarbamoyl chloride was then reacted with compound 3 to afford target 1 in 88% yield as a low melting yellow solid.…”