title: An intramolecular C-N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis.
abstract: 2-Aroylmethylidene-1,2,3,4-tetrahydroquinolines with the appropriate substituents can be suitable precursors for the synthesis of alkaloids from Galipea officinalis (cuspareine, galipeine, galipinine, angustureine). However, only two, rather low-yielding procedures for their synthesis are described in the literature. We have developed a simple and efficient protocol for an intramolecular, palladium or copper-catalysed amination of both chloro- and bromo-substituted 3-amino-1,5-diphenylpent-2-en-1-ones leading to the above-mentioned tetrahydroquinoline moiety. The methodology is superior to the methods published to date.
authors.affiliation: Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, CZ 532 10, Pardubice, Czech Republic.
authors.forename: Hana
authors.initials: H
authors.lastname: Doušová
authors.affiliation: Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, CZ 532 10, Pardubice, Czech Republic.
authors.forename: Radim
authors.initials: R
authors.lastname: Horák
authors.affiliation: Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, CZ 532 10, Pardubice, Czech Republic.
authors.forename: Zdeňka
authors.initials: Z
authors.lastname: Růžičková
authors.affiliation: Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, CZ 532 10, Pardubice, Czech Republic.
authors.forename: Petr
authors.initials: P
authors.lastname: Šimůnek
keywords: C–N cross-coupling; copper; enaminone; palladium; tetrahydroquinoline