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A modular synthesis of 1,4,5-trisubstituted 1,2,3-triazoles with ferrocene moieties

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Abstract

Regioselective synthesis of 1,2,3-triazoles with ferrocenyl moieties in positions 1, 4, and 5 was carried out in a two-step reaction sequence: a copper-mediated azide–alkyne cycloaddition followed by a palladium-catalyzed cross-coupling. A new route towards 5-iodo-1,2,3-triazoles was developed using N-iodomorpholine hydrogen iodide, instead of the corrosive and toxic ICl, as the I+ source. The novel methodology together with a consecutive Suzuki or Sonogashira reaction was shown to be a useful procedure for the synthesis of a wide range of ferrocenyl 1,2,3-triazoles with di- and triferrocenyl derivatives among them.

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References

  1. Pibiri I, Buscemi S (2010) Curr Bioact Comp 6:208

    Article  CAS  Google Scholar 

  2. Siddiqui N, Ahsan W, Alam MS, Ali R, Jain S, Azad B, Akhtar J (2011) Int J Pharm Sci Rev Res 8:161

    CAS  Google Scholar 

  3. Fouda MFR, Abd-Elzaher MM, Abdelsamaia RA, Labib AA (2007) Appl Organomet Chem 21:613

    Article  CAS  Google Scholar 

  4. Ornelas C (2011) New J Chem 35:1973

    Article  CAS  Google Scholar 

  5. Navarro M, Castro W, Biot C (2012) Organometallics 31:5715

    Article  CAS  Google Scholar 

  6. Braga SS, Silva AMS (2013) Organometallics 32:5626

    Article  CAS  Google Scholar 

  7. Kilpin KJ, Dyson PJ (2013) Chem Sci 4:1410

    Article  CAS  Google Scholar 

  8. Salmon AJ, Williams ML, Wu QK, Morizzi J, Gregg D, Charman SA, Vullo D, Supuran CT, Poulsen SA (2012) J Med Chem 55:5506

    Article  CAS  Google Scholar 

  9. Romero T, Orenes RA, Tárraga A, Molina P (2013) Organometallics 32:5740

    Article  CAS  Google Scholar 

  10. Molina P, Tárraga A, Caballero A (2008) Eur J Inorg Chem 3401

  11. Hildebrandt A, Lang H (2013) Organometallics 32:5640

    Article  CAS  Google Scholar 

  12. Rostovtsev VV, Green LK, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596

    Article  CAS  Google Scholar 

  13. Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057

    Article  Google Scholar 

  14. Orthaber A, Fuchs M, Belaj F, Rechberger GN, Kappe CO, Pietschnig R (2011) Eur J Inorg Chem 2588

  15. Balogh J, Skoda-Földes R (2011) Transition-metal catalyzed reactions in the synthesis of ferrocene. In: Phillips ES (ed) Ferrocenes: compounds, properties and applications. Nova Publishers, USA, pp 107–147

    Google Scholar 

  16. Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G (2005) J Am Chem Soc 127:15998

    Article  CAS  Google Scholar 

  17. Li LJ, Zhang YQ, Zhang Y, Zhu AL, Zhang GS (2014) Chin Chem Lett 25:1161

    Article  CAS  Google Scholar 

  18. Alonso F, Moglie Y, Radivoy G, Yus M (2012) Synlett 23:2179

    Article  CAS  Google Scholar 

  19. Ackermann L, Potukuchi HK, Landsberg D, Vicente R (2008) Org Lett 10:3081

    Article  CAS  Google Scholar 

  20. Deng J, Wu YM, Chen QY (2005) Synthesis 2730

  21. Morris JC, Chiche J, Grellier C, Lopez M, Bornaghi LF, Maresca A, Supuran CT, Pouysségur J, Poulsen SA (2011) J Med Chem 54:6905

    Article  CAS  Google Scholar 

  22. Joubert N, Schinazi RF, Agrofoglio LA (2005) Tetrahedron 61:11744

    Article  CAS  Google Scholar 

  23. Ostrowski T, Januszczyk P, Cieslak M, Kazmierczak-Baranska J, Nawrot B, Bartoszak-Adamska E, Zeidler J (2011) Bioorg Med Chem 19:4386

    Article  CAS  Google Scholar 

  24. García-Álvarez J, Díez J, Gimeno J, Suárez FJ, Vincent C (2012) Eur J Inorg Chem 5854

  25. Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Angew Chem Int Ed 48:8018

    Article  CAS  Google Scholar 

  26. Carcenac Y, David-Quillot F, Abarbri M, Duchêne A, Thibonnet J (2013) Synthesis 45:633

    Article  CAS  Google Scholar 

  27. Panteleev J, Geyer K, Aguilar-Aguilar A, Wang L, Lautens M (2010) Org Lett 12:5092

    Article  CAS  Google Scholar 

  28. Schulman JM, Friedman AA, Panteleev J, Lautens M (2012) Chem Commun 48:55

    Article  CAS  Google Scholar 

  29. Juríček M, Stout K, Kouwer PHJ, Rowan AE (2011) Org Lett 13:3494

    Article  Google Scholar 

  30. Bogdan AR, James K (2011) Org Lett 13:4060

    Article  CAS  Google Scholar 

  31. García-Álvarez J, Díez J, Gimeno J, Suárez FJ, Vincent C (2012) Eur J Inorg Chem 5854

  32. Cheng W, Jilin Y, Wei Z, Lan Z, Zheng Z (2013) J South Med Univ 33:779

    Google Scholar 

  33. Kuijpers BHM, Dijkmans GCT, Groothuys S, Quaedflieg PJLM, Blaauw RH, van Delft FL, Rutjes FPJT (2005) Synlett 3059

  34. Wu YM, Deng J, Li Y, Chen QY (2005) Synthesis 1314

  35. Li L, Zhang G, Zhu A, Zhang L (2008) J Org Chem 73:3630

    Article  CAS  Google Scholar 

  36. Li L, Li Y, Li R, Zhu A, Zhang G (2011) Aust J Chem 64:1383

    Article  CAS  Google Scholar 

  37. Yan R, El-Emir E, Rajkumar V, Robson M, Jathoul AP, Pedley RB, Årstad E (2011) Angew Chem Int Ed 50:6793

    Article  CAS  Google Scholar 

  38. Brotherton WS, Clark RJ, Zhu L (2012) J Org Chem 77:6443

    Article  CAS  Google Scholar 

  39. Barsoum DN, Brassard CJ, Deeb JHA, Okashah N, Sreenath K, Simmons JT, Zhu L (2013) Synthesis 45:2372

    Article  CAS  Google Scholar 

  40. Coutouli-Argyropoulou E, Tsitabani M, Petrantonakis G, Terzis A, Raptopoulou C (2003) Org Biomol Chem 1:1382

    Article  CAS  Google Scholar 

  41. Mamane V (2008) Mini-Rev Org Chem 5:303

    Article  CAS  Google Scholar 

  42. Kuik Á, Skoda-Földes R, Jánosi L, Kollár L (2007) Synthesis 1456

  43. Szánti-Pintér E, Balogh J, Csók Z, Kollár L, Gömöry Á, Skoda-Földes R (2011) Steroids 76:1377

    Google Scholar 

  44. Balogh J, Skoda-Földes R, Vazdar K, Habuš I (2012) J Organomet Chem 703:51

    Article  CAS  Google Scholar 

  45. Krasnova LB, Hein JE, Fokin VV (2010) J Org Chem 75:8662

    Article  CAS  Google Scholar 

  46. Urbán B, Srankó D, Sáfrán Gy, Ürge L, Darvas F, Bakos J, Skoda-Földes R (2014) J Mol Catal A 395:364

    Article  Google Scholar 

  47. Hein JE, Krasnova LB, Iwasaki M, Fokin VV (2011) Org Synth 88:238

    Article  CAS  Google Scholar 

  48. Wilkening I, del Signore G, Hackenberger CPR (2011) Chem Commun 47:349

    Article  CAS  Google Scholar 

  49. Casas-Solvas JM, Vargas-Berenguel A, Capitán-Vallvey LF, Santoyo-González F (2004) Org Lett 6:3687

    Article  CAS  Google Scholar 

  50. Broadhead GD, Osgerby JM, Pauson PL (1958) J Chem Soc 655

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Acknowledgments

The authors thank for the support of the Hungarian National Science Foundation (OTKA K105632) as well as the project TÁMOP-4.2.2.A-11/1/KONV-2012-0071, realized with the support of the Hungarian Government and the European Union, with the co-funding of the European Social Fund.

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Correspondence to Rita Skoda-Földes.

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Fehér, K., Gömöry, Á. & Skoda-Földes, R. A modular synthesis of 1,4,5-trisubstituted 1,2,3-triazoles with ferrocene moieties. Monatsh Chem 146, 1455–1463 (2015). https://doi.org/10.1007/s00706-015-1490-z

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  • DOI: https://doi.org/10.1007/s00706-015-1490-z

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