Reduction of Vicinal Tricarbonyl Compounds by Reduced Nicotinamide Adenine Dinucleotide Model and Electron-Transport Systems

Article abstract of DOI:10.1021/jo01301a023

The reduction of vicinal tricarbonyl compounds such as alloxan (A) and ninhydrin (NY) with 1-benzyl-1,4-dihydronicotinamide (BNAH; NADH model) was investigated.In the reduction of A with BNAH, the radical anion (A-.Py+) of A as the 1-benzyl-3-carbamoylpyridinium salt and the dialuric acid (D) was obtained by one-electron and two-electron reduction,respectively.Similarly,hydrindantin (HDT) and 2-hydroxy-1,3-indandione (HID) were also afforded in the reduction of NY with BNAH.Further,the reductions of alloxantin (AT) and HDT with BNAH were performed to give D and HID,respectively.The reduction of lipoic acid (LA) and viologens (V²⁺) with BNAH, which could not be reduced without A or NY, proceeded smoothly in their presence,and they proved to be useful as mediators for catalytic reduction of LA and V²⁺.