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Synthesis of γ-Sultam-Annelated δ-Lactams via the Castagnoli-Cushman Reaction of Sultam-Based Dicarboxylic Acids. 2022

Andrey Firsov, and Olga Bakulina, and Dmitry Dar'in, and Viktor V Sokolov, and Mikhail Krasavin
Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.

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 NH-sultam, which is not only suitable for further modification but represents a known pharmacophore for carbonic anhydrase inhibition.

UI MeSH Term Description Entries
D007769 Lactams Cyclic AMIDES formed from aminocarboxylic acids by the elimination of water. Lactims are the enol forms of lactams. Lactam,Lactim,Lactims
D009282 Naphthalenesulfonates A class of organic compounds that contains a naphthalene moiety linked to a sulfonic acid salt or ester.
D003998 Dicarboxylic Acids Acyclic acids that contain two carboxyl groups and have the formula HO2C-R-CO2H, where R may be an aromatic or aliphatic group. Acids, Dicarboxylic
D000812 Anhydrides Chemical compounds derived from acids by the elimination of a molecule of water. Anhydride

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