Skip to main content
Log in

Synthesis of Polycyclic (Hetero)Aromatic Hydrocarbons via the Friedel–Crafts/Bradsher Cyclization

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This review covers the literature on synthesis of polycyclic aromatic hydrocarbons via the Friedel–Crafts/Bradsher cyclization, published in the period of 1987–2016. Syntheses of partly and fully fused (hetero)aromatic systems with 5- or 6-membered rings formed upon the cyclization and containing C, O, S, N ring (hetero)atoms are reported in this work. All described aromatic systems have been formed in reactions using aromatic aldehydes and their derivatives as carbonyl reagents.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. (a) Troian-Gautier, L.; Moucheron, C. Molecules 2014, 19, 5028. (b) Lindhorst, A. C.; Haslinger, S.; Kühn, F. E. Chem. Commun. 2015, 51, 17193.

  2. (a) Introduction to Organic Electronic and Optoelectronic Materials and Devices; Sun, S.-S.; Dalton, L. R., Eds.; CRC Press: Boca Raton, 2008. (b) Organic Optoelectronic Materials; Li, Y., Ed.; Springer: New York, 2015. (c) Organic Photovoltaics: Materials, Device Physics, and Manufacturing Technologies; Brabec, C.; Scherf, U.; Dyakonov, V., Eds.; Wiley-VCH: Weinheim, 2014, 2nd ed.

  3. (a) Stockdale, T. P.; Williams, C. M. Chem. Soc. Rev. 2015, 44, 7737. (b) Liu, J.; Sridhar, J.; Foroozesh, M. Molecules 2013, 18, 14470. (c) Kovacic, P.; Somanathan R. Open J. Prev. Med. 2014, 4, 583. (d) Becker, F. F.; Banik, B. K. Front. Chem. 2014, 2, 55, DOI: 10.3389/fchem.2014.00055.

  4. Grzybowski, M.; Skonieczny, K.; Butenschön, H.; Gryko, D. T. Angew. Chem., Int. Ed. 2013, 52, 9900.

  5. Vilsmeier, A.; Haack, A. Ber. Dtsch. Chem. Ges. 1927, 60, 119.

    Article  Google Scholar 

  6. Gattermann, L.; Berchelmann, W. Ber. Dtsch. Chem. Ges. 1898, 31, 1765.

    Article  CAS  Google Scholar 

  7. Duff, J. C.; Bills, E. J. J. Chem. Soc. 1932, 1987. (b) Duff, J. C.; Bills, E. J. J. Chem. Soc. 1934, 1305.

  8. (a) Friedel, C., Crafts, J. M. C. R. Hebd. Séances Acad. Sci. 1877, LXXXIV, 1392. (b) Friedel, C.; Crafts, J. M. C. R. Hebd. Séances Acad. Sci. 1877, LXXXIV, 1450.

  9. (a) Bradsher, C. K. J. Am. Chem. Soc. 1940, 62, 486. (b) Bradsher, C. K. Chem. Rev. 1987, 87, 1277.

  10. (a) Aggarwal, N.; MacDowel, D. W. H. Organic Prep. Proced. Int. 1979, 11, 247. (b) Beimling, P.; Koßmehl, G. Chem. Ber. 1986, 119, 3198. (c) Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J.; Dodabalapur, A. Adv. Mater. 1997, 9, 36.

  11. Kuninobu, Y.; Tatsuzaki, T.; Matsuki, T.; Takai, K. J. Org. Chem. 2011, 76, 7005.

    Article  CAS  Google Scholar 

  12. Daich, A.; Ohier, P.; Decroix, B. Tetrahedron Lett. 1995, 36, 83.

    Article  CAS  Google Scholar 

  13. Du, C.; Guo, Y.; Chen, J.; Liu, H.; Liu, Y.; Ye, S.; Lu, K.; Zheng, J.; Wu, T.; Liu, Y.; Shuai, Z.; Yu, G. J. Phys. Chem. C 2010, 114, 10565.

    Article  CAS  Google Scholar 

  14. Rafiq, S. M.; Sivasakthikumaran, R.; Karunakaran, J.; Monanakrishnan, A. K. Eur. J. Org. Chem. 2015, 5099.

  15. Zhang, Q.; Peng, H.; Zhang, G.; Lu, Q.; Chang, J.; Dong, Y.; Shi, X.; Wei, J. J. Am. Chem. Soc. 2014, 136, 5057.

    Article  CAS  Google Scholar 

  16. Paul, K.; Bera, K.; Jalal, S.; Sarkar, S.; Jana, U. Org. Lett. 2014, 16, 2166.

    Article  CAS  Google Scholar 

  17. Paul, K.; Jalal, S.; Kundal, S.; Jann, U. J. Org. Chem. 2016, 81, 1164.

    Article  CAS  Google Scholar 

  18. Li, H.; Yang, J.; Liu, Y.; Li, Y. J. Org. Chem. 2009, 74, 6797.

    Article  CAS  Google Scholar 

  19. Li, Q.; Xu, W.; Hu, J.; Chen, X.; Zhang, F.; Zheng, H. RSC Adv. 2014, 4, 27722.

    Article  CAS  Google Scholar 

  20. Fraleoni-Morgera, A.; Zanirato, P. ARKIVOC 2006, (xii), 111.

  21. (a) Wex, B.; Kaafarani, B. R.; Neckers, D. C. J. Org. Chem. 2004, 69, 2197. (b) Wex, B.; Kaafarani, B. R.; Kirschbaum, K.; Neckers, D. C. J. Org. Chem. 2005, 70, 4502.

  22. Park, J. I.; Chung, J. W.; Kim, J.-Y.; Lee, J.; Jung, J. Y.; Koo, B.; Lee, B.-L.; Lee, S. W.; Jin, Y. W.; Lee, S. Y. J. Am. Chem. Soc. 2015, 137, 12175.

    Article  CAS  Google Scholar 

  23. Tylleman, B.; Vande Velde, C. M. L.; Balandier, J.-Y.; Stas, S.; Sergeyev, S.; Geerts, Y. H. Org. Lett. 2011, 13, 5208.

    Article  CAS  Google Scholar 

  24. (a) Mamada, M.; Minamiki, T.; Katagiri, H.; Tokito, S. Org. Lett. 2012, 14, 4062. (b) Mamada, M.; Katagiri, H.; Mizukami, M.; Honda, K.; Minamiki, T.; Teraoka, R.; Uemura, T.; Tokito, S. ACS Appl. Mater. Interfaces 2013, 5, 9670.

  25. Kowalska, E.; Bałczewski, P. Ultrason. Sonochem. 2017, 34, 743.

    Article  CAS  Google Scholar 

  26. (a) Bałczewski, P.; Koprowski, M.; Bodzioch, A.; Marciniak, B.; Różycka-Sokołowska E. J. Org. Chem. 2006, 71, 2899. (b) Bałczewski, P.; Bodzioch, A.; Różycka-Sokołowska, E.; Marciniak, B.; Uznański, P. Chem.–Eur. J. 2010, 16, 2392. (c) Bodzioch, A.; Marciniak, B.; Różycka-Sokołowska, E.; Jeszka, J. K.; Uznański, P.; Kania, S.; Kuliński, J.; Bałczewski, P. Chem.–Eur. J. 2012, 18, 4866. (d) Bałczewski, P.; Bodzioch, A.; Koprowski, M. PL Patent 219334. (e) Bałczewski, P.; Bodzioch, A.; Koprowski, M.; Skalik, J. PL Patent 219155. (f) Bałczewski, P.; Skalik, J.; Uznański, P.; Guziejewski, D.; Ciesielski, W. RSC Adv. 2015, 5, 24700.

  27. Krapcho, A. P.; Cadamuro, S. A.; Macnee, L. ARKIVOC 2007, (ix), 28.

  28. Krapcho, A. P.; Cadamuro, S. A. J. Heterocycl. Chem. 2004, 41, 291.

    Article  CAS  Google Scholar 

  29. Granzhan, A.; Bats, J. W.; Ihmels, H. Synthesis 2006, 1549.

  30. Sureshbabu, R.; Saravanan, V.; Dhayalan, V.; Monanakrishnan, A. K. Eur. J. Org. Chem. 2011, 922.

  31. Granzhan, A.; Ihmels, H.; Mikhlina, K.; Deiseroth, H.-J.; Mikus, H. Eur. J. Org. Chem. 2005, 4098.

  32. Clement, J. A.; Sivasakthikumaran, R.; Monanakrishnan, A. K.; Sundaramoorthy, S.; Velmurugan, D. Eur. J. Org. Chem. 2011, 569.

Download references

The project was financed by the National Science Centre, Poland, on the basis of the decision no. UMO-2013/11/B/ST5/01610.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Piotr Bałczewski.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(1), 11–20

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bodzioch, A., Kowalska, E., Skalik, J. et al. Synthesis of Polycyclic (Hetero)Aromatic Hydrocarbons via the Friedel–Crafts/Bradsher Cyclization. Chem Heterocycl Comp 53, 11–20 (2017). https://doi.org/10.1007/s10593-017-2015-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2015-y

Keywords

Navigation