Acid-Mediated Intramolecular Cyclizations of (<i>N</i>-Aryl)-acetylenic Sulfonamides: Synthesis of Fused and Spirocyclic Sultams

Herein, we report acid-mediated divergent annulations of (<i>N</i>-aryl)-alkynyl sulfonamides. The substituent at the <i>para</i> position of the <i>N</i>-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.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-09-14
DOI
https://doi.org/10.1021/acs.joc.4c01517
Citations
3
Primary Topic
Organic and Inorganic Chemical Reactions
Type
article
Field-Weighted Citation Impact
0.72

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article

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

Anjali Rathaur, Chada Raji Reddy, Banoth Karuna Sagar
3 citations
The Journal of Organic Chemistry
Organic and Inorganic Chemical Reactions
0.72
article

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

Anjali Rathaur, Chada Raji Reddy, Banoth Karuna Sagar
article en
3 citations

Abstract

Herein, we report acid-mediated divergent annulations of (<i>N</i>-aryl)-alkynyl sulfonamides. The substituent at the <i>para</i> position of the <i>N</i>-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.

The Journal of Organic ChemistryVol. 89(19)
Indian Institute of Chemical Technology (IN), Academy of Scientific and Innovative Research (IN)
Council of Scientific and Industrial Research, India, University Grants Commission, Science and Engineering Research Board
Clean water and sanitation
Openalex Percentile: Top 33%
Organic and Inorganic Chemical Reactions
0.72
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Acid-Mediated Intramolecular Cyclizations of (<i>N</i>-Aryl)-acetylenic Sulfonamides: Synthesis of Fused and Spirocyclic Sultams — Anjali Rathaur, Chada Raji Reddy, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS