Sisko, Joseph published the artcileAn investigation of imidazole and oxazole syntheses using aryl-substituted TosMIC reagents, SDS of cas: 263389-54-4, the main research area is imidazole phenyl preparation; oxazole aryl preparation; tosylmethyl isonitrile cyclocondensation imine; amine aldehyde tosylmethyl isonitrile cyclocondensation; amino acid aldehyde tosylmethylisonitrile cyclocondensation; aldehyde ammonium hydroxide cyclization tosylmethyl isonitrile.
Efficient and mild protocols are described for preparing polysubstituted imidazoles in a single pot from aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and an amine followed by addition of the TosMIC reagent gave 1,4,5-tri-substituted imidazoles with predictable regiochem. Thus, condensation of pyruvaldehyde with (MeO)2CHCH2NH2 in THF at ambient temperature for 15 min and subsequent reaction with 4-FC6H4CH(Tos)N+C- [Tos = 4-MeC6H4SO2] in the presence of piperazine for 18 h gave 71% [(fluorophenyl)imidazolyl]ethanone I. Employing chiral amines and aldehydes, particularly those derived from α-amino acids, gave imidazoles, e.g. II, with asym. centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles were also readily prepared by a simple variant of the above procedure. Selection of glyoxylic acid as the aldehyde component of the procedure lead to intermediates such as III which readily underwent decarboxylation and elimination of the tosyl moiety to give 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes gave 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles, e.g. IV, from these TosMIC reagents and aldehydes was described.
Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 263389-54-4 belongs to class nitriles-buliding-blocks, name is a-Tosyl-(4-methoxybenzyl) isocyanide, and the molecular formula is C16H15NO3S, SDS of cas: 263389-54-4.
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts