Regioselective C5-Alkylation and C5-Methylcarbamate Formation of 2,3-Dihydro-4-pyridones and C3-Alkylation and C3-Methylcarbamate Formation of 4-(Pyrrolidin-1-yl)furan-2(5H)-one.

Reactions of N-alkyl-2,3-dihydro-4-pyridones and 4-(pyrrolidin-1-yl)furan-2(5H)-one with aldehydes and triethylsilane in a one-flask procedure provided C5 and C3 alkylated derivatives, respectively. Mannich-type reactions with formaldehyde and carbamates in the presence of lithium perchlorate furnished C5/C3 methylcarbamates.