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

The replacement of the aromatic ring in bioactive compoundswithsaturated bioisosteres has become a popular tactic to obtain novelstructures with improved physicochemical profiles. In this paper,we describe an efficient synthesis of 3,5-methanobenzo[b]azepine analogues and suggest them as isosteres of quinolones. Quinolonesare heteroaromatic, flat rings and considered as privileged scaffolds.An isosteric version of this scaffold with more 3D character wouldoffer new options to expand their use.