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General One-Pot, Three-Step Methodology Leading to an Extended Class of N -Heterocyclic Cations: Spontaneous Nucleophilic Addition, Cyclization, and Hydride Loss

2004; American Chemical Society; Volume: 69; Issue: 18 Linguagem: Inglês

10.1021/jo0495440

1520-6904

Alexis D. C. Parenty, Louise V. Smith, A.L. Pickering, De‐Liang Long, Leroy Cronin,

Phenothiazines and Benzothiazines Synthesis and Activities

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.