title: 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.
abstract: Reactions ofN-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.
authors.affiliation: Department of Medicinal Chemistry, University of Kansas, Lawrence, KS 66045 ; Department of Medicinal Chemistry and Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414, USA.
authors.forename: Xingxian
authors.initials: X
authors.lastname: Gu
authors.affiliation: Department of Medicinal Chemistry and Institute for Therapeutics Discovery and Development, University of Minnesota, 717 Delaware Street SE, Minneapolis, Minnesota 55414, USA.
authors.forename: Gunda I
authors.initials: GI
authors.lastname: Georg
keywords: 2,3-dihydro-4-pyridones; 4-(pyrrolidin-1-yl)furan-2(5H)-one; Mannich reaction; regioselective alkylation