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Base Promoted 5-endo-dig Cyclizations of Non-Conia-ene Propargyl Ethers: A Mechanistic Investigation
Title
Base Promoted 5-endo-dig Cyclizations of Non-Conia-ene Propargyl Ethers: A Mechanistic Investigation.
Creator
Hintze, Silas Q., Lepore, Salvatore D., Florida Atlantic University, Department of Chemistry and Biochemistry, Charles E. Schmidt College of Science
Abstract/Description
Herein, we discuss a novel method for the synthesis of decorated 2,5-dihydrofurans. The base promoted 5-endo-dig cyclization of non-Conia-ene propargyl ethers produces 2,2 disubstituted dihydrofurans. Central to the reaction is the presence of an acidic C–H bond which is activated by an adjacent aromatic heterocycle. The transformation is viable with a wide range of substituents, including N, O, and S containing heterocycles, substituted phenyl rings, and alkyl groups. The cyclization...
Show moreHerein, we discuss a novel method for the synthesis of decorated 2,5-dihydrofurans. The base promoted 5-endo-dig cyclization of non-Conia-ene propargyl ethers produces 2,2 disubstituted dihydrofurans. Central to the reaction is the presence of an acidic C–H bond which is activated by an adjacent aromatic heterocycle. The transformation is viable with a wide range of substituents, including N, O, and S containing heterocycles, substituted phenyl rings, and alkyl groups. The cyclization proceeds within 30 seconds at room temperature under the action of potassium tert-butoxide. This work stands apart from the current literature due to the absence of transition metal catalysts and/or harsh reaction conditions. A thorough mechanistic investigation is undertaken to better understand the nature of this unprecedented reaction.
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Date Issued
2024
PURL
http://purl.flvc.org/fau/fd/FA00014376
Subject Headings
Cyclization (Chemistry), Chemistry, Organic
Format
Document (PDF)
Non-metal catalyzed cyclization of α-alkynyl hydrazines to form azaproline derivatives: a mechanism study
Title
Non-metal catalyzed cyclization of α-alkynyl hydrazines to form azaproline derivatives: a mechanism study.
Creator
Nagy, Edith, Maity, Pradip, Lepore, Salvatore D.
Date Issued
2012-04-06
PURL
http://purl.flvc.org/fcla/dt/3349037
Subject Headings
Synthetic organic chemistry, Alkynes, Non-metal catalyzed cyclization, Derivatization --proline, Pyrazolines -- Derivatives, Biochemical models, Hydrazines
Format
Document (PDF)