Skip to main content
SpringerLink
Log in

Synthesis of 1,3- and 1,2,3-functionalized pyrroles via Ir(I)-catalyzed vinylation of allyl alcohols

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

An efficient method for the preparation of 1,3-disubstituted and 1,2,3-trisubstituted pyrroles was developed through a sequence involving O-vinylation of allyl alcohols followed by Claisen rearrangement and further ozonolysis, concurring in a Paal–Knorr reaction with primary amines. Hg(II) and Ir(I) catalysts and different vinylating reagents were tested. The best results were consistently obtained with the [Ir(cod)Cl]2–vinyl acetate system. The featured methodology gives access to functionalized pyrroles in overall good yields, whose chemical architecture may awake interest for assorted applications.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1.

Similar content being viewed by others

References

  1. (a) Young, I. S.; Thornton, P. D.; Thompson, A. Nat. Prod. Rep. 2010, 27, 1801. (b) Seiple, I. B.; Su, S.; Young, I. S.; Lewis, C. A.; Yamaguchi, J.; Baran, P. S. Angew. Chem., Int. Ed. 2010, 49, 1095.

  2. Seidel, D.; Lynch, V.; Sessler, J. L. Angew. Chem., Int. Ed. 2002, 41, 1422.

    Article  CAS  Google Scholar 

  3. Walsh, C. T.; Garneau-Tsodikova, S.; Howard-Jones, A. R. Nat. Prod. Rep. 2006, 23, 517.

    Article  CAS  Google Scholar 

  4. (a) Anzenbacher, P.; Nishiyabu, R.; Palacios, M. A. Coord. Chem. Rev. 2006, 250, 2929. (b) Domingo, V. M.; Alemán, C.; Brillas, E.; Juliá, L. J. Org. Chem. 2001, 66, 4058.

  5. (a) Seth, B. K.; Ray, A.; Saha, A.; Saha, P.; Basu, S. J. Photochem. Photobiol., B 2014, 132, 72. (b) MacLean, P. D.; Chapman, E. E.; Dobrowolski, S. L.; Thompson, A.; Barclay, L. R. C. J. Org. Chem. 2008, 73, 6623.

  6. (a) Battilocchio, C.; Poce, G.; Alfonso, S.; Porretta, G. C.; Consalvi, S.; Sautebin, L.; Pace, S.; Rossi, A.; Ghelardini, C.; Mannelli, L. D. C.; Schenone, S.; Giordani, A.; Francesco, L. D.; Patrignani, P.; Biava, M. Bioorg. Med. Chem. 2013, 21, 3695. (b) Mohamed, M. S; Kamel, R.; Fathallah, S. S. Arch. Pharm. (Weinheim, Ger.) 2011, 344, 830.

  7. (a) Baran, P. S.; Richter, J. M.; Lin, D. W. Angew. Chem., Int. Ed. 2005, 44, 609. (b) Vyas, S.; Trivedi, P.; Chaturvedi, S. Acta Pharm. (Zagreb, Croatia) 2007, 57, 441.

  8. (a) Hilmy, K. M. H.; Soliman, D. H.; Shahin, E. B. A.; Alhameed, R. A. Life Sci. J. 2012, 9, 736. (b) Edwards, T. G.; Koeller, K. J.; Slomczynska, U.; Fok, K.; Helmus, M.; Bashkin, J. K.; Fisher, C. Antivir. Res. 2011, 91, 177.

  9. (a) Idhayadhulla, A.; Kumar, R. S.; Nasser, A. J. A.; Manilal, A. Bull. Chem. Soc. Ethiop. 2012, 26, 429. (b) El-Sayed, R.; Khairou, K. S. J. Surfactants Deterg. 2015, 18, 661.

  10. Gupton, J. T. Top. Heterocycl. Chem. 2006, 2, 53.

    CAS  Google Scholar 

  11. (a) Schneider, J. G.; Eynatten, M.; Parhofer, K. G.; Volkmer, J. E.; Schiekofer, S.; Hamann, A.; Nawroth, P. P.; Dugi, K. A. Atherosclerosis (Amsterdam, Neth.) 2004, 175, 325. (b) Krause, B. R.; Newton, R. S. Atherosclerosis 1995, 117, 237.

  12. (a) Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238. (b) Jacobi, P. A.; Coutts, L. D.; Guo, J.; Hauck, S. I.; Leung, S. H. J. Org. Chem. 2000, 65, 205. (c) Khan, A. T.; Lal, M.; Bagdi, P. R.; Basha, R. S.; Saravanan, P.; Patra, S. Tetrahedron Lett. 2012, 53, 4145. (d) Reddy, G. R.; Reddy, T. R.; Joseph, S. C.; Reddy, K. S.; Reddy, L. S.; Kumar, P. M.; Krishna, G. R.; Reddy, C. M.; Rambabu, D.; Kapavarapu, R.; Lakshmi, C.; Meda, T.; Priya, K.; Parsa, K. V. L.; Pal, M. Chem. Commun. 2011, 47, 7779.

  13. (a) Reddy, V. P.; Kumar, A. V.; Rao, K. R. Tetrahedron Lett. 2011, 52, 777. (b) Yan, R.-L.; Luo, J.; Wang, C.-X.; Ma, C.-W.; Huang, G.-S.; Liang, Y.-M. J. Org. Chem. 2010, 75, 5395. (c) Tamaddon, F.; Farahi, M.; Karami, B. J. Mol. Catal. A: Chem. 2012, 356, 85.

  14. Elming, N.; Clauson-Kaas, N. Acta Chem. Scand. 1952, 6, 867.

    Article  CAS  Google Scholar 

  15. (a) Veisi, H. Tetrahedron Lett. 2010, 51, 2109. (b) Cadierno, V.; Gimeno, J.; Nebra, N. Chem.–Eur. J. 2007, 13, 9973.

  16. (a) Humenny, W. J.; Kyriacou, P.; Sapeta, K.; Karadeolian, A.; Kerr, M. A. Angew. Chem. 2012, 124, 11250. (b) Estévez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2010, 39, 4402.

  17. Michlik, S.; Kempe, R. Nat. Chem. 2013, 5, 140.

    Article  CAS  Google Scholar 

  18. Kolos, N. N.; Zubar, V. V.; Omelchenko, I. V.; Musatov, V. I. Chem. Heterocycl. Compd. 2016, 52, 237. [Khim. Geterotsikl. Soedin. 2016, 52, 237.]

  19. Babaei, S. E.; Hossaini, Z.; Besheli, R. R.; Tavakkoli, V. Chem. Heterocycl. Compd. 2016, 52, 294. [Khim. Geterotsikl. Soedin. 2016, 52, 294.]

  20. Haraguchi, K.; Takahashi, H.; Shiina, N.; Horii, C.; Yoshimura, Y.; Nishikawa, A.; Sasakura, E.; Nakamura, K. T.; Tanaka, H. J. Org. Chem. 2002, 67, 5919.

    Article  CAS  Google Scholar 

  21. (a) Zhang, F.; Du, P.; Chen, J.; Wang, H.; Luo, Q.; Wan, X. Org. Lett. 2014, 16, 1932. (b) Yoo, E.-J.;Wasa, M.;Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 17378.

  22. (a) Buchi, G.; Vogel, D. E. J. Org. Chem. 1985, 50, 4664. (b) Morita, M.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2006, 71, 6285. (c) Ooi, T.; Takahashi, M.; Yamada, M.; Tayama, E.; Omoto, K.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 1150. (d) Wei, X.; Lorenz, J. C.; Kapadia, S.; Saha, A.; Haddad, N.; Busacca, C. A.; Senanayake, C. H. J. Org. Chem. 2007, 72, 4250.

  23. Watanabe, W. H.; Conlon, L. E. J. Am. Chem. Soc. 1957, 79, 2828.

    Article  CAS  Google Scholar 

  24. Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124, 1590.

    Article  CAS  Google Scholar 

  25. (a) Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tetrahedron Lett. 2005, 46, 2643. (b) Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213.

  26. (a) Méndez, J. M.; Flores, B.; León, F.; Martínez, M. E.; Vázquez, A.; García, G. A.; Salmón, M. Tetrahedron Lett. 1996, 37, 4099. (b) Kagabu, S.; Tsuji, H.; Kawai, I.; Ozeki, H. Bull. Chem. Soc. Jpn. 1995, 68, 341.

Download references

Thanks are given to Facultad de Química, UNAM for financial support and also CONACYT for scholarship to D. A. R. (CV/grant number 387462/255265). As well, we want to thank Dr. Rafael Omar Arcos Ramos and Professor Joseph Muchowski for the corrections to early manuscripts of this work. Deep gratitude is also expressed to the USAII division from Facultad de Química, UNAM and Dr. Rosa Santillan Baca for the acquisition of spectroscopic data and MS experiments, respectively.

Author information

Authors and Affiliations

  1. School of Chemistry, National Autonomous University of Mexico, Ciudad Universitaria, México, D. F., 04510, México

    David Alavez-Rosas, Mauricio Maldonado-Domínguez, Oscar González-Antonio, Margarita Romero-Ávila, José Méndez-Stivalet & Blas Flores-Pérez

Authors
  1. David Alavez-Rosas
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mauricio Maldonado-Domínguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Oscar González-Antonio
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Margarita Romero-Ávila
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. José Méndez-Stivalet
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Blas Flores-Pérez
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Blas Flores-Pérez.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 526–531

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alavez-Rosas, D., Maldonado-Domínguez, M., González-Antonio, O. et al. Synthesis of 1,3- and 1,2,3-functionalized pyrroles via Ir(I)-catalyzed vinylation of allyl alcohols. Chem Heterocycl Comp 53, 526–531 (2017). https://doi.org/10.1007/s10593-017-2087-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2087-8

Keywords

Search

Navigation