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

10 August 2023, Version 3
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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 communication, we describe an efficient synthesis of 3,5-methanobenzo[b]azepine analogs and suggest them as isosteres of quinolones. Quinolones are heteroaromatic, 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.

Keywords

3D character
isosteres
methanobenzo[b]azepines
chemical space

Supplementary materials

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