Journal of the Chemical Society. Perkin transactions I p. 2912 - 2919 (1981)
Update date:2022-08-02
Topics: Yield NMR spectroscopy reflux Chromatography Stirring TLC (thin-layer chromatography) Workup Reaction Setup Quenching Extraction Reduction Reaction Selective Reduction Lactams Magnesium (Mg) Carbonyl Group (C=O) Double Bond (C=C)
Brettle, Roger
Shibib, Sa'ad M.
αβ-Olefinic amides with various substitution patterns at the carbon-carbon double bond and at nitrogen are all reduced to the corresponding saturated amides by magnesium and methanol.The same reducing system reduces N-benzyl-8-azabicyclo<4.3.0>nona-1(6),3-dien-7-ones at the conjugated double bond to give mixtures of the cis- and trans-dihydro-derivatives; the isolated, non-conjugated double bond is not reduced, even in the 3,4-diphenylsubstituted compound.Magnesium and methanol reduces quinolin-2(1H)-ones to their 3,4-dihydro-derivatives, and 5,6,7,8-tetrahydroquinolin-2(1H)-one to a mixture of two dihydro-derivatives.
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