title: Transition-metal-free synthesis of 3-(1-pyrrolidinyl)quinolines and 3-(1-pyrrolidinyl)quinoline 1-oxides via a one-pot reaction of 3-(1-pyrrolidinyl)crotonates with nitrobenzenes.
abstract: A carbanion of tert-butyl 3-(1-pyrrolidinyl)crotonate adds to nitrobenzenes to form σH-adducts, which in the presence of pivaloyl chloride and triethylamine are converted into 3-(1-pyrrolidinyl)quinolines or 3-(1-pyrrolidinyl)quinoline 1-oxides depending on the nitrobenzene structure. This is the first methodology in which a quinoline ring is constructed from a substrate bearing a pyrrolidinyl ring. Starting from optically pure enamines, the method allows synthesis of the corresponding chiral products without racemisation.
authors.affiliation: Institute of Organic Chemistry Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warsaw, Poland. robert.bujok@icho.edu.pl krzysztof.wojciechowski@icho.edu.pl.
authors.forename: Robert
authors.initials: R
authors.lastname: Bujok
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.forename: Zbigniew
authors.initials: Z
authors.lastname: Wróbel
authors.forename: Krzysztof
authors.initials: K
authors.lastname: Wojciechowski