86668-17-9Relevant academic research and scientific papers
Redox-Photosesitized Reactions. 13. Ru(bpy)32+ -Photosensitized Reactions of an NADH Model, 1-Benzyl-1,4-dihydronicotinamide, with Aromatic Carbonyl Compounds and Comparision with Thermal Reactions
Ishitani, Osamu,Yanagida, Shozo,Takamuku, Setsuo,Pac, Chyongjin
, p. 2790 - 2796 (2007/10/02)
Photosensitized reactions of 1-benzyl-1,4-dihydronicotinamide (BNAH) with aromatic carbonyl compounds (1a-f) by Ru(bpy)32+ have been investigated.The reduction to the corresponding alcohols occurs with di-2-pyridyl ketone (1a) in a quantitative yield and with methyl benzoylformate (1b) in a 18percent yield.Noteworthy is the efficient formation of 1:1 adducts 4b-f, a new class of 4-alkyl 1,4-dihydronicotamides, in 55-85percent isolated yields; 4b is a single isomer of a condensed bicyclic imide, whereas the other adducts are obtained as diastereoisomeric mixtures.In the case oftrifluoroacetophenone (1c), the diastereoisomeric 6-alkylated 1,6-dihydronicotamides (4c') are formed as minor 1:1 adducts.The structure of each adduct has been determined by spectroscopic and X-ray crystallographic studies with one exception (4d).The mechanism of the photosensitized reactions is discussed in terms of sequential indirect electron-proton transfer from BNAH to 1a-f followed by electron transfer or cross-coupling between radical intermediates.On the other hand thermal reactions of NAH with 1a-e in the dark give neither the adduct nor the half-oxidized dimers of BNAH but the alcohols.It is suggested that electron-transfer mechanisms are not responsible for the thermal reactions.
Formation of a Novel Type of Adduct between an NADH Model and Carbonyl Compounds by Photosensitization Using Ru(bpy)32+
Ishitani, Osamu,Pac, Chyongjin,Sakurai, Hiroshi
, p. 2941 - 2942 (2007/10/02)
The Ru(bpy)32+-photosensitized reaction of 1-benzyl-1,4-dihydronicotinamide with several aromatic carbonyl compounds gave 1:1 adducts of the 4-substituted dihydronicotinamide structure in moderate to good yields along with less efficient reduction or no reduction to the corresponding alcohols; di-2-pyridyl ketone was exclusively reduced to the alcohol.
