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

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

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 diast...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 87; no. 2; pp. 1537 - 1540
Main Authors: Firsov, Andrey, Bakulina, Olga, Dar’in, Dmitry, Sokolov, Viktor V, Krasavin, Mikhail
Format: Journal Article
Language:English
Published: United States American Chemical Society 21-01-2022
Subjects:
Anhydrides
Dicarboxylic Acids
Lactams
Naphthalenesulfonates
Online Access:Get full text
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Summary: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.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02456