Cyclic amidine synthesis via dearomatization strategy: Utility of the intermediate

초록

The amidine functional group is ubiquitous in biologically active molecules. In particular, cyclic amidines are important structural motifs in various natural and pharmaceutical compounds with a wide range of bioactivities. Therefore, the development of efficient synthetic routes to this moiety starting from a readily available molecule is of great interest. Among the various synthetic methods to synthesize cyclic amidines, the [3 + 2] cycloaddition of azide and enamine is one of the most versatile strategies. Whereas linear enamines have been well studied in this context of cycloaddition, endocyclic enamine has been less explored for cyclic amidine synthesis. Meanwhile, the regioselective dearomatization of readily available aromatic compound becomes an emerging strategy to obtain complex molecules. Selective dearomatization of the Nheteroarene might be an attractive approach to reach the endocyclic enamines. In this presentation, an efficient synthetic route to cyclic amidines from readily available quinolines via the one-pot process of dearomative hydrosilylation and enamine-azide [3 + 2] cycloaddition will be discussed.