Biotinの合成研究(第1報) : 4,5-二置換4-imidazolin-2-one類の接触還元

概要

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In order to obtain compounds available for the synthesis of biotin, catalytic hydrogenation of 4,5-disubstituted-4-imidazolin-2-ones was examined. 4-Phenyl-5-hydroxymethyl derivative (IV) was hydrogenated over palladium-carbon to its corresponding 2-imidazolidone derivative (XVI). Further, hydrogenation of XVI with the Adams catalyst led to the formation of cyclohexyl derivative (XVII). Cross conjugation between the carbonyl group at position 4,and the imidazolone ring increased stability, and made the ring difficult to be hydrogenated. The compounds VIII and XI resisted hydrogenation of the ring, and reduction of carbonyl group or C-O bond fission at position 5 was predominant. Even in the hydrogenation of 1,3-diacetyl derivatives (X and XIII) with rhodium or palladium catalyst C-O bond fission occurred preferentially to reduction of the ring. Catalytic hydrogenation of dihydrothienoimidazolone compound (XV) resulted in desulfurization.
公益社団法人日本薬学会の論文
1968-04-25