General one-pot, three-step methodology leading to an extended class of N-heterocyclic cations: spontaneous nucleophilic addition, cyclization, and hydride loss

The Journal of Organic Chemistry
Alexis D C ParentyLeroy Cronin

Abstract

A new class of phenanthridinium derivative has been isolated from the reaction of 2-bromoethyl-phenanthridinium bromide with a range of primary amines in excellent yields. The reaction pathway is unprecedented and proceeds via three cascade steps: nucleophilic attack of a primary amine on the iminium moiety of a heteroaromatic ring system and cyclization to form a five-membered ring, followed by hydride loss to yield a rearomatized dihydro-1H-imidazo[1,2-f]phenanthridinium derivative. A range of NMR phase transfer experiments were carried out to elucidate the mechanistic pathway, and the methodology has been further developed by means of a biphasic system using N-bromosuccinimide as a co-oxidizing agent. The method has also been extended to other N-heterocyclic cation derivatives such as quinolinium and quinazolinium.

Citations

Dec 5, 2012·Journal of the American Chemical Society·Maialen Espinal ViguriIrene Ara
Jun 6, 2009·Journal of the American Chemical Society·Geoffrey J T Cooper, Leroy Cronin
Dec 5, 2009·Journal of the American Chemical Society·Kevin L MillerPaula L Diaconescu
Apr 24, 2012·Nature Chemistry·Mark D SymesLeroy Cronin
Jun 21, 2007·Chemical Communications : Chem Comm·Nicola McMillanLeroy Cronin
Jul 2, 2009·Chemical Communications : Chem Comm·Philip J KitsonLeroy Cronin
Jun 18, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rui YangHui-Ling Geng
Sep 9, 2011·Angewandte Chemie·Geoffrey J T CooperLeroy Cronin
Apr 3, 2014·Chemistry : a European Journal·Maialen Espinal ViguriLucía Riera
Oct 13, 2006·Chembiochem : a European Journal of Chemical Biology·Louise V SmithLeroy Cronin
Oct 8, 2009·The Journal of Organic Chemistry·Craig J RichmondLeroy Cronin
Sep 4, 2008·Journal of the American Chemical Society·Craig J RichmondLeroy Cronin
Feb 8, 2018·Bioconjugate Chemistry·Silvan D BossSimon M Ametamey
May 15, 2019·The Journal of Organic Chemistry·Mani RamanathanShiuh-Tzung Liu

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