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Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres

✍ Scribed by Elisa Perissutti; Francesco Frecentese; Ferdinando Fiorino; Beatrice Severino; Donatella Cirillo; Vincenzo Santagada; Giuseppe Caliendo

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
327 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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1,3 Dipolar cycloaddition of Fmoc‐amino azides and acetylenic amides produces under solvent free irradiation a mixture of 1,4 or 1,5 substituted [1,2,3]‐triazoles. The presence of copper (I) iodide, plays a central role on regioselectivity. Four Fmoc‐amino azides characterized by different steric hindrance in side chains, and three different terminal alkynes, provided only the 1,4 substituted regioisomer under thermal microwave heating. Good yields, low consumption of organic solvents and short reaction times are the main aspects of our procedure. Reactions are compared to regioselective copper (I) catalysed solution synthesis performed at room temperature.

πŸ“œ SIMILAR VOLUMES

Microwave Solvent-Free Regioselective 1,
Microwave Solvent-Free Regioselective 1,3-Dipolar Cycloaddition in the Synthesis of 1,4-Substituted[1,2,3]-triazoles as Amide Bond Isosteres.
✍ Elisa Perissutti; Francesco Frecentese; Ferdinando Fiorino; Beatrice Severino; D πŸ“‚ Article πŸ“… 2007 πŸ› John Wiley and Sons βš– 23 KB πŸ‘ 1 views

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