2-Substituted 4-azaindoles and indoles are rapidly and efficiently prepared in an activation-free Pd-catalyzed alkynylation–cyclization sequence starting from 3-amino-2-bromopyridine or o-bromoaniline and terminal alkynes in a one-pot fashion.
Similar content being viewed by others
References
Sundberg, R. J. The Chemistry of Indoles; Academic Press: New York, 1970.
Netz, N.; Opatz, T. Mar. Drugs 2015, 13, 4814.
Aygun, A.; Pindur, U. Curr. Med. Chem. 2003, 10, 1113.
Gul, W.; Hamann, M. T. Life Sci. 2005, 78, 442.
Schmidt, A. M.; Eilbracht, P. J. Org. Chem. 2005, 70, 5528.
Johansson, H.; Bøgeløv Jørgensen, T.; Gloriam, D. E.; Bräuner-Osborne, H.; Pedersen, D. S. RSC Adv. 2013, 3, 945.
Meredith, P.; Riesz, J. Photochem. Photobiol. 2004, 79, 211.
Krüger, K.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2153.
Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
Taber, D. F.; Tirunahari, P. K. Tetrahedron 2011, 67, 7195.
Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, 215.
D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095.
Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101.
Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Eur. J. Org. Chem. 2002, 2671.
Martinez-Outschoorn, U. E.; Peiris-Pages, M.; Pestell, R. G.; Sotgia, F.; Lisanti, M. P. Nat. Rev. Clin. Oncol. 2017, 14, 11.
Flick, A. C.; Ding, H. X.; Leverett, C. A.; Kyne, R. E., Jr.; Liu, K. K.-C.; Fink, S. J.; O'Donnell, C. J. Bioorg. Med. Chem. 2016, 24, 1937.
Welsch, M. E.; Snyder, S. A.; Stockwell, B. R. Curr. Opin. Chem. Biol. 2010, 14, 347.
Davies, T. G.; Woodhead, S. J.; Collins, I. Curr. Top. Med. Chem. 2009, 9, 1705.
Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
Rathi, A. K.; Syed, R.; Singh, V.; Shin, H.-S.; Patel, R. V. Recent Pat. Anti-Cancer Drug Discovery 2017, 12, 55.
Asati, V.; Bharti, S. K.; Mahapatra, D. K.; Asati, V.; Budhwani, A. K. Curr. Pharm. Des. 2016, 22, 6039.
Blanco-Aparicio, C.; Carnero, A. Biochem. Pharmacol. 2013, 85, 629.
Mérour, J.-Y.; Buron, F.; Ple, K.; Bonnet, P.; Routier, S. Molecules 2014, 19, 19935.
Zhou, Q.; Phoa, A. F.; Abbassi, R. H.; Hoque, M.; Reekie, T. A.; Font, J. S.; Ryan, R. M.; Stringer, B. W.; Day, B. W.; Johns, T. G.; Munoz, L.; Kassiou, M. J. Med. Chem. 2017, 60, 2052.
Feneyrolles, C.; Guiet, L.; Singer, M.; Van Hijfte, N.; Dayde-Cazals, B.; Fauvel, B.; Cheve, G.; Yasri, A. Bioorg. Med. Chem. Lett. 2017, 27, 862.
Kim, J.; Moon, Y.; Hong, S. Bioorg. Med. Chem. Lett. 2016, 26, 5669.
Stanton, R. A.; Lu, X.; Detorio, M.; Montero, C.; Hammond, E. T.; Ehteshami, M.; Domaoal, R. A.; Nettles, J. H.; Feraud, M.; Schinazi, R. F. Bioorg. Med. Chem. Lett. 2016, 26, 4101.
Wucherer-Plietker, M.; Merkul, E.; Müller, T. J. J.; Esdar, C.; Knochel, T.; Heinrich, T.; Buchstaller, H.-P.; Greiner, H.; Dorsch, D.; Finsinger, D.; Calderini, M.; Bruge, D.; Grädler, U. Bioorg. Med. Chem. Lett. 2016, 26, 3073.
Dayde-Cazals, B.; Fauvel, B.; Singer, M.; Feneyrolles, C.; Bestgen, B.; Gassiot, F.; Spenlinhauer, A.; Warnault, P.; Van Hijfte, N.; Borjini, N.; Cheve, G.; Yasri, A. J. Med. Chem. 2016, 59, 3886.
Liu, N.; Wang, Y.; Huang, G.; Ji, C.; Fan, W.; Li, H.; Cheng, Y.; Tian, H. Bioorg. Chem. 2016, 65, 146.
Baltus, C. B.; Jorda, R.; Marot, C.; Berka, K.; Bazgier, V.; Krystof, V.; Prie, G.; Viaud-Massuard, M.-C. Eur. J. Med. Chem. 2016, 108, 701.
Dias Pires, M. J.; Poeira, D. L.; Marques, M. M. B. Eur. J. Org. Chem. 2015, 7197.
Mérour, J.-Y.; Routier, S.; Suzenet, F.; Joseph, B. Tetrahedron 2013, 69, 4767.
Popowycz, F.; Routier, S.; Joseph, B.; Mérour, J.-Y. Tetrahedron 2007, 63, 1031.
Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120.
Nordmann, J.; Müller, T. J. J. Synthesis 2014, 522.
Nordmann, J.; Müller, T. J. J. Org. Biomol. Chem. 2013, 11, 6556.
Nordmann, J.; Breuer, N.; Müller, T. J. J. Eur. J. Org. Chem. 2013, 4303.
Lessing, T.; Sterzenbach, F.; Müller, T. J. J. Synlett 2015, 1217.
Lessing, T.; Müller, T. J. J. Synlett 2017, 1743.
Goehrlich, J. R.; Schmutzler, R. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 102, 211.
Tewari, A.; Hein, M.; Zapf, A.; Beller, M. Synthesis 2004, 935.
Pena-Lopez, M.; Neumann, H.; Beller, M. Chem.–Eur. J. 2014, 20, 1818.
Perea-Buceta, J. E.; Wirtanen, T.; Laukkanen, O.-V.; Makela, M. K.; Nieger, M.; Melchionna, M.; Huittinen, N.; Lopez-Sanchez, J. A.; Helaja, J. Angew. Chem., Int. Ed. 2013, 52, 11835.
Jiang, H.; Fu, H.; Qiao, R.; Jiang, Y.; Zhao, Y. Synthesis 2008, 2417.
The authors cordially thank the Fonds der Chemischen Industrie for financial support (scholarship for Timo Lessing).
The authors cordially thank the microanalytical laboratory of the Institut für Medizinische und Pharmazeutische Chemie at the Heinrich-Heine-Universität Düsseldorf for the elemental analyses measurment.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(3), 334–338
Electronic supplementary material
ESM 1
(PDF 1290 kb)
Rights and permissions
About this article
Cite this article
Lessing, T., Müller, T.J.J. Activation-free one-pot alkynylation–cyclization synthesis of 2-substituted 4-azaindoles and indoles. Chem Heterocycl Comp 54, 334–338 (2018). https://doi.org/10.1007/s10593-018-2269-z
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-018-2269-z