Synthesis of 4-Aryl-1H-1,2,3-triazoles through TBAF-Catalyzed [3 + 2] Cycloaddition of 2-Aryl-1-nitroethenes with TMSN3 under Solvent-Free Conditions
- 9 July 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (16), 6526-6529
- https://doi.org/10.1021/jo0507845
Abstract
TBAF-catalyzed [3 + 2] cycloaddition reactions of 2-aryl-1-cyano- or 2-aryl-1-carbethoxy-1-nitroethenes 1 with TMSN3 under SFC allow the corresponding 4-aryl-5-cyano- or 4-aryl-5-carbethoxy-1H-1,2,3-triazoles 2 to be prepared under mild reaction conditions and with good to excellent yields (70-90%). The proposed protocol does not require dried glassware or inert atmosphere.Keywords
This publication has 24 references indexed in Scilit:
- Copper(I)-Catalyzed Synthesis of Azoles. DFT Study Predicts Unprecedented Reactivity and IntermediatesJournal of the American Chemical Society, 2004
- Dendronized Linear Polymers via “Click Chemistry”Journal of the American Chemical Society, 2004
- TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under Solventless ConditionsThe Journal of Organic Chemistry, 2004
- Synthesis of Triazoles from Nonactivated Terminal Alkynes via the Three-Component Coupling Reaction Using a Pd(0)−Cu(I) Bimetallic CatalystJournal of the American Chemical Society, 2003
- Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamidesBioorganic & Medicinal Chemistry Letters, 2000
- Highly fluorinated acetylenes. Preparation and some cyclization reactionsThe Journal of Organic Chemistry, 1975
- 1.5‐Dipolare Cyclisierungen, II. ν‐Triazole aus Vinylaziden sowie durch Addition des Azid‐Ions an die CC‐DreifachbindungEuropean Journal of Inorganic Chemistry, 1970
- Small-ring epoxides. I. Synthesis and reactions of a 4-methylene-1-oxaspiro[2.2]pentane derivativeThe Journal of Organic Chemistry, 1968
- Über N‐Aminoalkyl‐1.2.3‐triazoleEuropean Journal of Organic Chemistry, 1965
- Some Derivatives of 3-Pyridol with Parasympathomimetic Properties1Journal of the American Chemical Society, 1951