Preparation of 3,5-methanobenzo[b]azepines: a novel sp3-rich Quinolone Isostere.


The replacement of the aromatic ring in bioactive com-pounds with saturated bioisosteres has become a popular tactic to obtain novel structures with an improved physico-chemical profile. In this communication, we describe an efficient synthesis of 3,5-methanobenzo[b]azepines and suggest them as isosteres of quinolones. Quinolones are aromatic, flat rings and considered as privileged scaffolds. An isosteric version of this scaffold with more 3D character would offer new options to expand their use.

Version notes

The conditions of schemes 4 and 5 were updated


Supplementary material

Supporting Information
Experimental protocol and compounds characterizations NMR spectra of new compounds