5-Substituted and 5,5-disubstituted hydantoins are synthesised from the corresponding aldehydes or ketones, using a one-pot, gallium(III) triflate-catalysed procedure that is compatible with a range of substrates and solvents.
[thiazolium-2,2 0 -14 C 2 ]-SAR97276A, a bis(thiazolium) antimalarial development candidate, was synthesized from [ 14 C]-thiourea with an overall radiochemical yield of 15%. The synthetic route involves a modified procedure for the synthesis of [ 14 C]-sulfurol, also a key intermediate in thiamine synthesis, which was developed due to unlabelled chemistry proving irreproducible with the radiolabelled substrate.
With a view to make conveniently labeled mass spectrometry standards available, a set of deuterated sphingomyelins were prepared by a new expedient, flexible, robust, scalable, and high-yielding synthetic scheme starting from 2-azido-3-O-benzoylsphingosine as the key intermediate. Unlike previously published procedures, this work emphasizes the benefit arising from the choice of the azido function as a masking group for the reactive primary amine during the troublesome, though crucial, phosphorylation step.
Imidazole derivatives R 0190Facile One-Pot Synthesis of 5-Substituted Hydantoins. -The method involves formation of nitriles from aldehydes or ketones and liq. ammonia, the conversion into amino nitriles by reaction with HCN, and final transformation of the latter to hydantoins by treatment with gaseous CO2. Gallium triflate as Lewis acid catalyst is present in all three steps. The difficulties associated with the isolation and purification of the amino nitriles are avoided. Compared to the two-pot procedure, the yields are higher in all cases, although both methods cannot be directly compared as the catalyst is used only in the one-pot procedure. -(MURRAY, R. G.; WHITEHEAD, D. M.; LE STRAT, F.; CONWAY*, S. J.; Org. Biomol. Chem. 6 (2008) 6, 988-991; Sch. Chem.,
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