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, Donatella Cirillo, Vincenzo Santagada, Giuseppe Caliendo

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)815-819
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume44
Issue number4
Publication statusPublished - Jul 2007

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Triazoles
Azides
Cycloaddition
Amides
Microwaves
Regioselectivity
Microwave heating
Alkynes
Organic solvents
Copper
Irradiation
Temperature
Hot Temperature
cuprous iodide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Perissutti, E., Frecentese, F., Fiorino, F., Severino, B., Cirillo, D., Santagada, V., & Caliendo, G. (2007). Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres. Journal of Heterocyclic Chemistry, 44(4), 815-819.

Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres. / Perissutti, Elisa; Frecentese, Francesco; Fiorino, Ferdinando; Severino, Beatrice; Cirillo, Donatella; Santagada, Vincenzo; Caliendo, Giuseppe.

In: Journal of Heterocyclic Chemistry, Vol. 44, No. 4, 07.2007, p. 815-819.

Research output: Contribution to journalArticle

Perissutti, E, Frecentese, F, Fiorino, F, Severino, B, Cirillo, D, Santagada, V & Caliendo, G 2007, 'Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres', Journal of Heterocyclic Chemistry, vol. 44, no. 4, pp. 815-819.
Perissutti, Elisa ; Frecentese, Francesco ; Fiorino, Ferdinando ; Severino, Beatrice ; Cirillo, Donatella ; Santagada, Vincenzo ; Caliendo, Giuseppe. / Microwave solvent free regioselective 1,3 dipolar cycloaddition in the synthesis of 1,4 substituted [1,2,3]-triazoles as amide bond isosteres. In: Journal of Heterocyclic Chemistry. 2007 ; Vol. 44, No. 4. pp. 815-819.
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