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Synlett 2012; 23(18): 2609-2614
DOI: 10.1055/s-0032-1317379
letter
© Georg Thieme Verlag Stuttgart · New York

Exploration of the CuAAC Reaction for the Synthesis of Novel 3-(Triazol-1-yl)methyl-imidazo[1,2-a]pyridines

Poonam Khedar
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India   Fax: +91(1596)244183   eMail: anilkumar@bits-pilani.ac.in
,
Kasiviswanadharaju Pericherla
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India   Fax: +91(1596)244183   eMail: anilkumar@bits-pilani.ac.in
,
Anil Kumar*
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India   Fax: +91(1596)244183   eMail: anilkumar@bits-pilani.ac.in
› Institutsangaben
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Publikationsverlauf

Received: 25. August 2012

Accepted after revision: 11. September 2012

Publikationsdatum:
18. Oktober 2012 (online)

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Abstract

The archetypical CuAAC click chemistry is explored to assemble diverse 3-(triazol-1-yl)methyl-imidazo[1,2-a]pyridines. The approach is simple, general, and environmentally benign to generate a library of novel triazolo-imidazo[1,2-a]pyridine derivatives in good yield (30–90%).

Key words

azides - click chemistry - imidazo[1,2-a]pyrimidine 1,2,3-triazole - 3-(triazolyl)methyl-imidazo[1,2-a]pyridine

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett. Full experimental details and characterization data 1H NMR, 13C NMR, HRMS and copies of 1H NMR and 13C NMR of 6 are included.
  • Supporting Information
 

  • References and Notes

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  • 39 General Procedure for the Preparation of 3-(Triazol-1-yl)methyl-imidazo[1,2-a]pyridines (6) To a 25 mL round-bottom flask was added 3-(azidomethyl)-2-pheny-lH-imidazo[1,2-a]pyridine (1.0 mmol), phenylacetylene (1.2 mmol), CuI (0.05 mmol), and PEG-400–H2O (1:1 v/v) (10 mL). The resulting mixture was stirred at r.t. for 5–7 h. After completion of the reaction H2O (20 mL) was added to the reaction mixture and extracted with EtOAc (3 × 10 mL). The combined organic layer was dried over anhyd Na2SO4 and evaporated the volatiles. The crude was purified by column over silica gel to give 6.
  • 40 Spectroscopic Data of Selected Compounds 6 Compound 6b: 1H NMR (500 MHz, CDCl3): δ = 8.16 (d, J = 6.8 Hz, 1 H), 7.72 (d, J = 9.1 Hz, 1 H), 7.69 (dd, J = 3.3, 1.1 Hz, 1 H), 7.68–7.66 (m, 5 H), 7.50 (s, 1 H), 7.35–7.31 (m, 1 H), 6.92 (d, J = 1.7 Hz, 1 H), 6.90 (t, J = 3.2 Hz, 2 H), 6.02 (s, 2 H), 3.82 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 159.8, 148.6, 132.3, 132.1, 131.2, 130.0, 128.6, 127.0, 126.5, 123.8, 123.2, 122.6, 117.8, 117.8, 114.2, 113.8, 105.4, 55.3, 43.9. ESI-MS: m/z = 460 [M + H]+. Compound 6d: 1H NMR (500 MHz, DMSO-d 6): δ = 8.73 (s, 1 H), 8.69 (s, 2 H), 8.37 (s, 1 H), 8.27 (d, J = 7.3 Hz, 1 H), 7.83 (d, J = 6.9 Hz, 4 H), 7.47–7.39 (m, 3 H), 7.31 (t, J = 6.9 Hz, 1 H), 7.09 (d, J = 5.4 Hz, 1 H), 6.26 (s, 2 H). 13C NMR (126 MHz, DMSO-d 6): δ = 148.6, 147.0, 134.6, 130.9, 129.3, 128.5, 126.9, 125.7, 124.5, 123.2, 123.1, 122.0, 122.0, 117.7, 113.8, 43.5. ESI-MS: m/z = 397 [M + H]+. Compound 6j: 1H NMR (500 MHz, CDCl3): δ = 8.12 (d, J = 6.7 Hz, 1 H), 7.70 (d, J = 9.0 Hz, 1 H), 7.65 (d, J = 8.3 Hz, 2 H), 7.46 (d, J = 8.2 Hz, 2 H), 7.31 (dd, J = 8.4, 7.4 Hz, 1 H), 7.26–7.25 (m, 1 H), 7.24 (s, 1 H), 7.19 (t, J = 5.5 Hz, 3 H), 7.05 (s, 1 H), 6.89 (t, J = 6.8 Hz, 1 H), 5.91 (s, 2 H), 4.02 (s, 2 H). 13C NMR (126 MHz, CDCl3): δ = 148.5, 145.1, 138.6, 134.8, 131.6, 130.6, 129.8, 129.4, 129.2, 128.6, 128.6, 126.6, 126.3, 123.9, 120.6, 117.8, 113.6, 43.8, 32.2. ESI-MS: m/z = 400 [M + H]+. Compound 6k: 1H NMR (500 MHz, CDCl3): δ = 8.12 (d, J = 6.8 Hz, 1 H), 7.70 (t, J = 8.9 Hz, 3 H), 7.49 (d, J = 8.4 Hz, 2 H), 7.33–7.29 (m, 1 H), 7.10 (s, 1 H), 6.89 (t, J = 6.7 Hz, 1 H), 5.95 (s, 2 H), 2.63 (t, J = 7.6 Hz, 2 H), 1.64–1.62 (m, 2 H), 0.91 (t, J = 7.4 Hz, 3 H). 13C NMR (126 MHz, CDCl3): δ = 149.3, 143.0, 134.8, 131.8, 129.7, 129.3, 126.2, 125.9, 125.4, 123.8, 119.8, 117.8, 113.6, 43.7, 27.7, 22.6, 13.7. ESI-MS: m/z = 352 [M + H]+. Compound 6o: 1H NMR (500 MHz, CDCl3): δ = 8.13 (d, J = 6.7 Hz, 1 H), 7.73 (dd, J = 7.9, 5.4 Hz, 5 H), 7.55 (s, 1 H), 7.34–7.29 (m, 1 H), 7.07 (dd, J = 9.4, 8.2 Hz, 4 H), 6.89 (t, J = 6.7 Hz, 1 H), 6.04 (s, 2 H), 3.88 (s, 3 H). 13C NMR (126 MHz, CDCl3): δ = 160.2, 147.8, 145.6, 130.9, 129.8, 128.8, 127.5, 127.5, 126.3, 125.3, 123.7, 118.5, 117.5, 115.9, 115.8, 114.6, 113.6, 55.4, 44.1. ESI-MS: m/z = 400 [M + H]+.