Synthesis of phenylacetylene containing 1,2,3-triazole group

Synthesis of phenylacetylene containing 1,2,3-triazole group Bromination of (E)-1-[4-(2-carboxy-vinyl)phenyl]-[1,2,3]triazole-4-carboxylic acid ethyl ester, which was synthesized in 90% yield by a Huisgen-type [3 + 2]-cycloaddition reaction between 3-(4-azidophenyl) acrylic acid and ethyl propiolate, in CHCl3 followed by a debrominative decarboxylation reaction with Et3N in DMF under microwave irradiation condition afforded stereoselective (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in 94% yield. Treatment of (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester with EtONa in DMF afforded 1-(4-ethynylphenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in a yield of 90%. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Synthesis of phenylacetylene containing 1,2,3-triazole group

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Publisher
Springer Netherlands
Copyright
Copyright © 2009 by Springer Science+Business Media BV
Subject
Chemistry; Inorganic Chemistry ; Physical Chemistry ; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-009-0065-1
Publisher site
See Article on Publisher Site

Abstract

Bromination of (E)-1-[4-(2-carboxy-vinyl)phenyl]-[1,2,3]triazole-4-carboxylic acid ethyl ester, which was synthesized in 90% yield by a Huisgen-type [3 + 2]-cycloaddition reaction between 3-(4-azidophenyl) acrylic acid and ethyl propiolate, in CHCl3 followed by a debrominative decarboxylation reaction with Et3N in DMF under microwave irradiation condition afforded stereoselective (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in 94% yield. Treatment of (Z)-1-(4-(2-bromovinyl)phenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester with EtONa in DMF afforded 1-(4-ethynylphenyl)-1,2,3-triazole-4-carboxylic acid ethyl ester in a yield of 90%.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Aug 11, 2009

References

  • 1,2,3-triazole formation under mild conditions via 1,3-dipolar cycloaddition of acetylenes with azides
    Katritzky, AR; Zhang, Y; Singh, SK
  • The growing impact of click chemistry on drug discovery
    Kolb, HC; Sharpless, KB
  • Combining biginelli multicomponent and click chemistry: generation of 6-(1,2,3-triazol-1-yl)dihydropyrimidone libraries
    Khanetskyy, B; Dallinger, D; Kappe, CO
  • Substituent effects on the antibacterial activity of nitrogen-carbon-linked (azolylphenyl)oxazolidinones with expanded activity against the fastidious Gram-negative organisms Haemophilus influenzae and Moraxella catarrhalis
    Genin, MJ; Allwine, DA; Anderson, DJ; Barbachyn, MR; Emmert, DE; Garmon, SA; Graber, DR; Grega, KC; Hester, JB; Hutchinson, DK; Morris, J; Reischer, RD; Stper, D; Yagi, BH

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