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Paper | Special issue | Vol 93, No. 2, 2016, pp.613-627
Published online, 3rd December, 2015
DOI: 10.3987/COM-15-S(T)51
Synthesis of 5-Aminobenzoimidazo[1,2-a]Quinoline Derivatives Through One-Pot Two-Step Cascade Reaction

Jun-ya Kato, Yutaro Ito, Ryosuke Ijuin, Hiroshi Aoyama, and Tsutomu Yokomatsu*

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

An efficient method for the synthesis of 5-aminobenzimidazo[1,2-a]quinolines with high diversity has been developed through a cascade reaction involving sequential aromatic nucleophilic substitution and the Dieckmann–Thorpe cyclization. This method is applicable to the synthesis of a wide range of 5-aminobenzimidazo[1,2-a]quinoline derivatives from readily available 2-fluoroarylnitriles and benzimidazole substrates. Moderate light emission was observed for some 5-aminobenzimidazo[1,2-a]quinolines.