A Synthetic Route Toward Highly Functionalized Pyrrole and 1,2,3‐Triazole Derivatives from Trichloroacetamidine, Alkynes and Tosylmethyl Isocyanide or Sodium Azide

Abstract In this research we report our results on a simple and efficient method for the synthesis of a variety of pyrroles with sulfone and amidine substitutions via the four‐component reaction of alkynes, tosylmethyl isocyanide, trichloroacetonitrile, and various anilines in good yields. Using an inexpensive copper(I) catalyst, MeCN solvent, and ultrasonication for 60 min in the absence of ligands and oxidants, these novel heterocyclic compounds were synthesized and characterized. Furthermore, the reaction under similar conditions with sodium azide substituted for tosyl methyl isocyanide, led to the synthesis of interesting 1,2,3‐triazole derivatives including amidine substitutions in good yields.

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Journal
ChemistrySelect
Published
2025-09-29
DOI
https://doi.org/10.1002/slct.202501736
Primary Topic
Click Chemistry and Applications
Type
article
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article

A Synthetic Route Toward Highly Functionalized Pyrrole and 1,2,3‐Triazole Derivatives from Trichloroacetamidine, Alkynes and Tosylmethyl Isocyanide or Sodium Azide

Manijeh Nematpour
ChemistrySelect
Click Chemistry and Applications
article

A Synthetic Route Toward Highly Functionalized Pyrrole and 1,2,3‐Triazole Derivatives from Trichloroacetamidine, Alkynes and Tosylmethyl Isocyanide or Sodium Azide

Manijeh Nematpour
article en

Abstract

Abstract In this research we report our results on a simple and efficient method for the synthesis of a variety of pyrroles with sulfone and amidine substitutions via the four‐component reaction of alkynes, tosylmethyl isocyanide, trichloroacetonitrile, and various anilines in good yields. Using an inexpensive copper(I) catalyst, MeCN solvent, and ultrasonication for 60 min in the absence of ligands and oxidants, these novel heterocyclic compounds were synthesized and characterized. Furthermore, the reaction under similar conditions with sodium azide substituted for tosyl methyl isocyanide, led to the synthesis of interesting 1,2,3‐triazole derivatives including amidine substitutions in good yields.

ChemistrySelectVol. 10(37)
Farhangian University (IR)
Openalex Percentile: Top 80%
Click Chemistry and Applications
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