Preparation of 3,5-Methanobenzo[]azepines: An sp-Rich Quinolone Isostere.

The replacement of the aromatic ring in bioactive compounds with saturated bioisosteres has become a popular tactic to obtain novel structures with improved physicochemical profiles. In this paper, we describe an efficient synthesis of 3,5-methanobenzo[]azepine analogues and suggest them as isosteres of quinolones. Quinolones are heteroaromatic, flat rings and considered as privileged scaffolds.