AI Article Synopsis
- An innovative type of reactive sultam-based dicarboxylic acids and anhydrides was used in the Castagnoli-Cushman reaction, resulting in diastereomerically pure products at room temperature.
- The initial products tended to decarboxylate due to steric hindrance, leading to a mixture of bicyclic sultam lactams that could be separated using HPLC.
- Selecting the right protecting group on the sultam nitrogen allows for the release of the sultam, which is useful for further modifications and functions as a pharmacophore for inhibiting carbonic anhydrase.
Article Abstract
An unusual type of highly reactive sultam-based dicarboxylic acids and correscponding anhydrides was employed in the Castagnoli-Cushman reaction delivering diastereomerically pure adducts at room temperature. Due to steric congestion, the initial adducts were prone to decarboxylation affording diastereomeric mixtures of bicyclic sultam lactams, separable by HPLC. The choice of a protecting group on the sultam nitrogen atom allows liberation of the -sultam, which is not only suitable for further modification but represents a known pharmacophore for carbonic anhydrase inhibition.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.1c02456 | DOI Listing |
Publication Analysis
Top Keywords
castagnoli-cushman reaction
8
sultam-based dicarboxylic
8
dicarboxylic acids
8
synthesis γ-sultam-annelated
4
γ-sultam-annelated δ-lactams
4
δ-lactams castagnoli-cushman
4
reaction sultam-based
4
acids unusual
4
unusual type
4
type highly
4
Similar Publications
Want AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!