Coenzyme models. VIII. Reduction of the Schiff base of pyridoxal analogs by 1,4-dihydronicotinamide.
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概要
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Reduction of Schiff bases by 1-benzyl-1,4-dihydronicotinamide (BzlNH) was performed in refluxing methanol. Protonated imines such as <I>N</I>-(<I>p</I>-nitrobenzylidene)benzylamme hydrochloride (<B>1H</B><SUP>+</SUP>) and <I>N</I>-(4-nitrosalicylidene)benzylamine hydrochloride (<B>1</B>(<B>OH</B>)<B>H</B><SUP>+</SUP>) were reduced to the corresponding aminomethyl derivatives. The NMR product analysis for the reaction of BzlNH and <B>1H</B><SUP>+</SUP> in refluxing ethanol-<I>d</I> established that the solvent deuteron was not incorporated into the aminomethylene product. <B>1</B>(<B>OH</B>), unprotonated species, was partially reducible, whereas <B>1</B> was totally unreactive. The facile reduction of <B>1</B> occurred in the presence of several amine hydrochlorides (NEt<SUB>3</SUB>·HCl, imidazole hydrochloride, <I>N</I>,<I>N</I>,<I>N</I>′,<I>N</I>′-tetramethylethylenediamine dihydrochloride). These results show that the <I>ortho</I> hydroxyl group of <B>1</B>(<B>OH</B>) facilitates imine reduction not only by polarization of the Schiff base <I>via</I> hydrogen bonding but also by proton transfer. The relative reactivity of the Schiff base to the BzlNH reduction is: <B>1H</B><SUP>+</SUP>, <B>1</B>+NEt<SUB>3</SUB>·HCl≥<B>1</B>(<B>OH</B>)<B>H</B><SUP>+</SUP>><B>1</B>(<B>OH</B>)><B>1</B>(unreactive) This order is similar to that found in "trans-Schiffization" between semicarbazide and the Schiff base of pyridoxal and its analogs, as reported by Gordes and Jencks.
- 公益社団法人 日本化学会の論文
著者
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Kunitake Toyoki
Department Of Chemical Engineering & Technology Faculty Of Engineering Kyushu University
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Shinkai Seiji
Department Of Applied Chemistry Faculty Of Engineering Kyushu University
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Shiraishi Sumihiro
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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