Partial reduction of pyridinium salts as a versatile route to dihydropyridones.
[reaction: see text] The addition of two electrons to a pyridinium salt turns it into a nucleophile. The intermediate generated by the reduction of such salts can be reacted successfully with a range of different electrophiles (acids, alkyl halides, and carbonyl compounds) and the intermediate hydrolyzed in situ to provide a wide range of dihydropyridones. Each position on the dihydropyridone ring is then accessible using standard synthetic manipulations.
Donohoe
Timothy J
TJ
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. Timothy.Donohoe@chem.ox.ac.uk
Johnson
Dale J
DJ
Mace
Laura H
LH
Bamford
Mark J
MJ
Ichihara
Osamu
O
D018360:Crystallography, X-Ray; D004583:Electrons; D006868:Hydrolysis; D007202:Indicators and Reagents; D011726:Pyridinium Compounds / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D011726:Pyridinium Compounds; D011728:Pyridones