title: 1-Alkyl- and (±)-1,2-dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones by a tandem Michael-SNAr annulation reaction.
abstract: A tandem Michael-S(N)Ar annulation reaction has been developed for the synthesis of 1-alkyl and (±)-1,2-dialkyl-2,3-dihydro-1,8-naphthyridin-4(1H)-ones. Treatment of 1-(2-chloropyridin-3-yl)prop-2-en-1-one (R = H) or (E or Z)-1-(2-chloropyridin-3-yl)but-2-en-1-one (R = CH3) with R'NH2 in DMF at 50 °C for 24 h provides 2,3-dihydro-1,8-naphthyridin-4(1H)-ones in 65-85% yields. Mechanistic studies suggest that the reaction sequence is initiated by Michael addition to the side chain enone.
authors.affiliation: Department of Chemistry, Oklahoma State University, Stillwater, Oklahoma 74078-3071, United States. rab@okstate.edu
authors.forename: Richard A
authors.initials: RA
authors.lastname: Bunce
authors.forename: Scott T
authors.initials: ST
authors.lastname: Squires
authors.forename: Baskar
authors.initials: B
authors.lastname: Nammalwar