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.
Graphical abstract
Similar content being viewed by others
References
Pibiri I, Buscemi S (2010) Curr Bioact Comp 6:208
Siddiqui N, Ahsan W, Alam MS, Ali R, Jain S, Azad B, Akhtar J (2011) Int J Pharm Sci Rev Res 8:161
Fouda MFR, Abd-Elzaher MM, Abdelsamaia RA, Labib AA (2007) Appl Organomet Chem 21:613
Ornelas C (2011) New J Chem 35:1973
Navarro M, Castro W, Biot C (2012) Organometallics 31:5715
Braga SS, Silva AMS (2013) Organometallics 32:5626
Kilpin KJ, Dyson PJ (2013) Chem Sci 4:1410
Salmon AJ, Williams ML, Wu QK, Morizzi J, Gregg D, Charman SA, Vullo D, Supuran CT, Poulsen SA (2012) J Med Chem 55:5506
Romero T, Orenes RA, Tárraga A, Molina P (2013) Organometallics 32:5740
Molina P, Tárraga A, Caballero A (2008) Eur J Inorg Chem 3401
Hildebrandt A, Lang H (2013) Organometallics 32:5640
Rostovtsev VV, Green LK, Fokin VV, Sharpless KB (2002) Angew Chem Int Ed 41:2596
Tornøe CW, Christensen C, Meldal M (2002) J Org Chem 67:3057
Orthaber A, Fuchs M, Belaj F, Rechberger GN, Kappe CO, Pietschnig R (2011) Eur J Inorg Chem 2588
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
Zhang L, Chen X, Xue P, Sun HHY, Williams ID, Sharpless KB, Fokin VV, Jia G (2005) J Am Chem Soc 127:15998
Li LJ, Zhang YQ, Zhang Y, Zhu AL, Zhang GS (2014) Chin Chem Lett 25:1161
Alonso F, Moglie Y, Radivoy G, Yus M (2012) Synlett 23:2179
Ackermann L, Potukuchi HK, Landsberg D, Vicente R (2008) Org Lett 10:3081
Deng J, Wu YM, Chen QY (2005) Synthesis 2730
Morris JC, Chiche J, Grellier C, Lopez M, Bornaghi LF, Maresca A, Supuran CT, Pouysségur J, Poulsen SA (2011) J Med Chem 54:6905
Joubert N, Schinazi RF, Agrofoglio LA (2005) Tetrahedron 61:11744
Ostrowski T, Januszczyk P, Cieslak M, Kazmierczak-Baranska J, Nawrot B, Bartoszak-Adamska E, Zeidler J (2011) Bioorg Med Chem 19:4386
García-Álvarez J, Díez J, Gimeno J, Suárez FJ, Vincent C (2012) Eur J Inorg Chem 5854
Hein JE, Tripp JC, Krasnova LB, Sharpless KB, Fokin VV (2009) Angew Chem Int Ed 48:8018
Carcenac Y, David-Quillot F, Abarbri M, Duchêne A, Thibonnet J (2013) Synthesis 45:633
Panteleev J, Geyer K, Aguilar-Aguilar A, Wang L, Lautens M (2010) Org Lett 12:5092
Schulman JM, Friedman AA, Panteleev J, Lautens M (2012) Chem Commun 48:55
Juríček M, Stout K, Kouwer PHJ, Rowan AE (2011) Org Lett 13:3494
Bogdan AR, James K (2011) Org Lett 13:4060
García-Álvarez J, Díez J, Gimeno J, Suárez FJ, Vincent C (2012) Eur J Inorg Chem 5854
Cheng W, Jilin Y, Wei Z, Lan Z, Zheng Z (2013) J South Med Univ 33:779
Kuijpers BHM, Dijkmans GCT, Groothuys S, Quaedflieg PJLM, Blaauw RH, van Delft FL, Rutjes FPJT (2005) Synlett 3059
Wu YM, Deng J, Li Y, Chen QY (2005) Synthesis 1314
Li L, Zhang G, Zhu A, Zhang L (2008) J Org Chem 73:3630
Li L, Li Y, Li R, Zhu A, Zhang G (2011) Aust J Chem 64:1383
Yan R, El-Emir E, Rajkumar V, Robson M, Jathoul AP, Pedley RB, Årstad E (2011) Angew Chem Int Ed 50:6793
Brotherton WS, Clark RJ, Zhu L (2012) J Org Chem 77:6443
Barsoum DN, Brassard CJ, Deeb JHA, Okashah N, Sreenath K, Simmons JT, Zhu L (2013) Synthesis 45:2372
Coutouli-Argyropoulou E, Tsitabani M, Petrantonakis G, Terzis A, Raptopoulou C (2003) Org Biomol Chem 1:1382
Mamane V (2008) Mini-Rev Org Chem 5:303
Kuik Á, Skoda-Földes R, Jánosi L, Kollár L (2007) Synthesis 1456
Szánti-Pintér E, Balogh J, Csók Z, Kollár L, Gömöry Á, Skoda-Földes R (2011) Steroids 76:1377
Balogh J, Skoda-Földes R, Vazdar K, Habuš I (2012) J Organomet Chem 703:51
Krasnova LB, Hein JE, Fokin VV (2010) J Org Chem 75:8662
Urbán B, Srankó D, Sáfrán Gy, Ürge L, Darvas F, Bakos J, Skoda-Földes R (2014) J Mol Catal A 395:364
Hein JE, Krasnova LB, Iwasaki M, Fokin VV (2011) Org Synth 88:238
Wilkening I, del Signore G, Hackenberger CPR (2011) Chem Commun 47:349
Casas-Solvas JM, Vargas-Berenguel A, Capitán-Vallvey LF, Santoyo-González F (2004) Org Lett 6:3687
Broadhead GD, Osgerby JM, Pauson PL (1958) J Chem Soc 655
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.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-015-1490-z