- One-Pot Synthesis of 5-Amino-1,2,3-triazole Derivatives via Dipolar Azide?Nitrile Cycloaddition and Dimroth Rearrangement under Solvent-Free Conditions
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An efficient one-pot methodology for the preparation of 5-amino-1,2,3-triazole derivatives based on the combination of dipolar azide?nitrile cycloaddition with Dimroth rearrangement under solvent-free conditions has been developed.
- Gribanov, Pavel S.,Atoian, Edita M.,Philippova, Anna N.,Topchiy, Maxim A.,Asachenko, Andrey F.,Osipov, Sergey N.
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supporting information
p. 1378 - 1384
(2021/02/26)
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- Azide-acetonitrile "click" reaction triggered by Cs2CO3: The atom-economic, high-yielding synthesis of 5-amino-1,2,3-triazoles
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Medicinally important 5-amino-1,2,3-triazoles were synthesized using a novel Cs2CO3-catalyzed azide-acetonitrile[3 + 2]-cycloaddition. Aryl azides and aryl acetonitriles were employed in this transformation resulting in excellent yie
- Krishna, Patoju M.,Ramachary, Dhevalapally B.,Peesapati, Sruthi
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p. 62062 - 62066
(2015/08/03)
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- An Improved Procedure for the Preparation of 1-Benzyl-1H-1,2,3-triazoles from Benzyl Azides.
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A procedure for the preparation of substituted 1-benzyl-1H-1,2,3-triazoles from benzyl azides under very mild conditions is described.The method provides improved yields and extends the scope of the Dimroth Reaction to other types of active methylene compound to those previously used.Benzyl azides react with active methylene compounds in dimethyl sulphoxide catalysed by potassium carbonate at 35-40 deg C to give 1H-1,2,3-triazoles usually in good yield.Acetonitrile derivatives gave 5-amino-1H-1,2,3-triazoles whereas diethyl malonate gave 5-hydroxy-1H-1,2,3-triazoles. 1H-1,2,3-Triazole-4-carboxylate esters and 1H-1,2,3-triazole-4-ketones were obtained from ethyl acetoacetate and β-diketones respectively.Benzyl methyl ketone reacted to give 5-methyl-4-phenyl-1H-1,2,3-triazole, but acetone and acetophenone failed to react.Other active methylene compounds which did not react under these reaction conditions included ethyl cyanoacetate, ethyl fluoroacetate and ethyl nitroacetate.
- Cottrell, Ian F.,Hands, David,Houghton, Peter G.,Humphrey, Guy R.,Wright, Stanley H. B.
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p. 301 - 304
(2007/10/02)
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