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

Parenty, A.D.C., Smith, L.V., Pickering, A.L., Long, D.-L. and Cronin, L. (2004) General one-pot, three-step methodology leading to an extended class of N-heterocyclic cations: spontaneous nucleophilic addition, cyclization, and hydride loss. Journal of Organic Chemistry, 69(18), pp. 5934-5946. (doi: 10.1021/jo0495440)

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-1<I>H</I>-imidazo[1,2-<I>f</I>]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 <I>N</I>-bromosuccinimide as a co-oxidizing agent. The method has also been extended to other <I>N</I>-heterocyclic cation derivatives such as quinolinium and quinazolinium.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Parenty, Mr Alexis and Long, Dr Deliang and Cronin, Professor Lee
• Authors: Parenty, A.D.C., Smith, L.V., Pickering, A.L., Long, D.-L., and Cronin, L.
• Subjects: Q Science > QD Chemistry; Q Science > QH Natural history > QH345 Biochemistry
• College/School: College of Science and Engineering > School of Chemistry; University Centres > Glasgow Materials Research Initiative
• Journal Name: Journal of Organic Chemistry
• ISSN: 0022-3263