TBAF-promoted carbanion-mediated sulfonamide cyclization of CF<sub>3</sub>-substituted<i>N</i>-allenamides: an access to fluorinated γ-sultams-Reference-Cited by-同舟云学术

TBAF-promoted carbanion-mediated sulfonamide cyclization of CF₃-substitutedN-allenamides: an access to fluorinated γ-sultams

Published:2023 Issue:16 Volume:10 Page:4055-4060
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Gommenginger Clément¹^ORCID,Zheng Yongxiang¹,Maccarone Daniele²^ORCID,Ciofini Ilaria²,Miesch Laurence¹^ORCID

Affiliation:

1. Equipe Synthèse Organique et Phytochimie, Institut de Chimie, CNRS-UdS, UMR 7177, 4 rue Blaise Pascal, CS 90032, 67081, Strasbourg, France

2. Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences, Chemical Theory and Modelling Group, F-75005 Paris, France

Abstract

γ-Sultams bearing a trifluorinated ethyl- or an ene-gem-difluorinated tether were obtained from CF3-substitutedN-allenamides; experimental and DFT calculations suggested that this transformation involves a 5-endo-digcyclization on the ene-ynamide generatedin situ.

Funder

Centre National de la Recherche Scientifique

Université de Strasbourg

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2023/QO/D3QO00781B

Reference29 articles.

1. J. E.Lesch , The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine , Oxford University Press , Oxford , 2007

2. Sultams: Recent Syntheses and Applications

3. Sultiame revisited: treatment of refractory absence seizures

4. Novel Antiarthritic Agents with 1,2-Isothiazolidine-1,1-dioxide (γ-Sultam) Skeleton: Cytokine Suppressive Dual Inhibitors of Cyclooxygenase-2 and 5-Lipoxygenase

5. The Evolving Role of Taurolidine in Cancer Therapy

Cited by 2 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. γ-CF₃-Allenamides versus 3-CF₃-Cyclopentenylamines: Substituent-Controlled Divergent Reaction of β-CF₃-1,3-Enynamides with β-Dicarbonyl Compounds;The Journal of Organic Chemistry;2024-09-10

2. Metal free regio – and stereoselective semireduction of CF₃-substituted N-allenamides;Organic & Biomolecular Chemistry;2024