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2005
Fused pyridine derivatives
R 0450
General One-Pot, Three-Step Methodology Leading to an Extended Class of
Cations: Spontaneous Nucleophilic Addition, Cyclization, and Hy01- 129 N-Heterocyclic
dride Loss. — Treatment of 2-bromomethylpyridinium salts with primary amines offers a novel, general, and efficient one-pot approach to fused imidazolium compounds
such as (III) (V), (VI), (VIII), and (XI) which are of biological interest. The pathway is
unprecedented and proceeds via nucleophilic attack of amine on the iminium moiety
followed by 5-membered ring closure and hydride loss. Interestingly, reaction of the
salt (If) with aniline gives the quinoline derivative (IX) which does not undergo aromatization under the conditions used. — (PARENTY, A. D. C.; SMITH, L. V.;
PICKERING, A. L.; LONG, D.-L.; CRONIN*, L.; J. Org. Chem. 69 (2004) 18,
5934-5946; Dep. Chem., Univ. Glasgow, Glasgow G12 8QQ, UK; Eng.) — Jannicke
2005
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