Acid-Mediated Intramolecular Cyclizations of (N‑Aryl)-acetylenic Sulfonamides: Synthesis of Fused and Spirocyclic Sultams

Herein, we report acid-mediated divergent annulations of (N-aryl)-alkynyl sulfonamides. The substituent at the para position of the N-aryl group determines two diverse reaction paths, leading to the selective assembly of benzo-fused sultams and spirocyclic sultams. This strategy provides a series of...

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Bibliographic Details
Published in:Journal of organic chemistry 2024-10, Vol.89 (19), p.14120-14128
Main Authors: Raji Reddy, Chada, Rathaur, Anjali, Karuna Sagar, Banoth
Format: Article
Language:English
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Summary:Herein, we report acid-mediated divergent annulations of (N-aryl)-alkynyl sulfonamides. The substituent at the para position of the N-aryl group determines two diverse reaction paths, leading to the selective assembly of benzo-fused sultams and spirocyclic sultams. This strategy provides a series of benzo/spiro-sultams with wide functional group compatibility and good to excellent yields under mild reaction conditions. Additionally, scale-up reaction and further transformations of the products were also carried out to demonstrate the utility of the protocol.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c01517