Advertisement

Chemistry of Heterocyclic Compounds

, Volume 54, Issue 4, pp 394–396 | Cite as

Open image in new window 4-Hydroxycoumarins as Michael donors in asymmetric routes to polycyclic coumarins (microreview)

Article
  • 20 Downloads

Different [3,4]-fused polycyclic 2H-chromen-2-ones can be prepared in a stereoselective fashion starting from 4-hydroxycoumarins as nucleophilic synthones. Herein we report a brief overview of the most recent methods including Pd-catalyzed [3+3] annulation processes, organocatalytic one-pot and domino Michael addition/cyclization, tandem conjugate addition/hydroxyalkylation, and organocascade catalytic reaction.

References

  1. 1.
    Xie, L.; Yu, D.; Wild, C.; Allaway, G.; Turpin, J.; C. Smith, P. C.; Lee, K.-H. J. Med. Chem. 2004, 47, 756.Google Scholar
  2. 2.
    Pisani, L.; Catto, M.; Nicolotti, O.; Grossi, G.; Di Braccio, M.; Soto-Otero, R.; Mendez-Alvarez, E.; Stefanachi, A.; Gadaleta, D.; Carotti, A. Eur. J. Med. Chem. 2013, 70, 723.CrossRefGoogle Scholar
  3. 3.
    Pisani, L.; Catto, M.; De Palma, A.; Farina, R.; Cellamare, S.; Altomare, C. D. ChemMedChem 2017, 12, 1349.CrossRefGoogle Scholar
  4. 4.
    Pisani, L.; Rullo, M.; Catto, M.; de Candia, M.; Carrieri, A.; Cellmare, S.; Altomare, C. D. J. Sep. Sci. 2018, 41, 1376.CrossRefGoogle Scholar
  5. 5.
    Lake, B. G. Food Chem. Toxicol. 1999, 37, 423.CrossRefGoogle Scholar
  6. 6.
    Pisani, L.; Barletta, M.; Soto-Otero, R.; Nicolotti, O.; Mendez-Alvarez, E.; Catto, M.; Introcaso, A.; Stefanachi, A.; Cellamare, S.; Altomare, C.; Carotti, A. J. Med. Chem. 2013, 56, 2651.CrossRefGoogle Scholar
  7. 7.
    Tan, X.; Soualmia, F.; Furio, L.; Renard, J.-F.; Kempen, I.; Qin, L.; Pagano, M.; Pirotte, B.; El Amri, C.; Hovnanian, A.; Reboud-Ravaux, M. J. Med. Chem. 2015, 58, 598.CrossRefGoogle Scholar
  8. 8.
    Halland, N.; Hansen, T.; Jørgensen, K. A. Angew. Chem., Int . Ed. 2003, 42, 4955.CrossRefGoogle Scholar
  9. 9.
    Zhang, G.; Zhang, Y.; Yan, J.; Chen, R.; Wang, S.; Ma, Y.; Wang, R. J. Org. Chem. 2012, 77, 878.CrossRefGoogle Scholar
  10. 10.
    Jiang, X.; Sun, Y.; Yao, J.; Cao, Y.; Kai, M.; He, N.; Zhang, X.; Wang, Y.; Wang, R. Adv. Synth. Catal. 2012, 354, 917.CrossRefGoogle Scholar
  11. 11.
    Gurubrahamam, R.; Gao, B.-F.; Chen, Y.; Chan, Y.-T.; Tsai, M.-K.; Chen, K. Org. Lett. 2016, 18, 3098.CrossRefGoogle Scholar
  12. 12.
    Biswas, S.; Dagar, A.; Mobin, S. M.; Samanta, S. Org. Biomol. Chem. 2016, 14, 1940.CrossRefGoogle Scholar
  13. 13.
    Sagar, R.; Park, J.; Koh, M.; Park, S. B. J. Org. Chem. 2009, 74, 2171.CrossRefGoogle Scholar
  14. 14.
    Yetra, S. R.; Roy, T.; Bhunia, A.; Porwal, D.; Biju, A. T. J. Org. Chem. 2014, 79, 4245.CrossRefGoogle Scholar
  15. 15.
    Itoh, K.; Hasegawa, M.; Tanaka, J.; Kanemasa, S. Org. Lett. 2005, 7, 979.CrossRefGoogle Scholar
  16. 16.
    Wang, S.; Xiao, J.; Li, J.; Xiang, H.; Wang, C.; Carter, R. G.; Chen, X.; Yang, H. Chem. Commun. 2017, 53, 4441.CrossRefGoogle Scholar
  17. 17.
    Modrocka, V.; Veverkova, E.; Baran, R.; Sebesta, R. ChemistrySelect 2018, 3, 1466.CrossRefGoogle Scholar
  18. 18.
    Rueping, M.; Parra, A.; Uria, U.; Besselievre, F.; Merino, E. Org. Lett. 2010, 12, 5680.CrossRefGoogle Scholar
  19. 19.
    Hack, D.; Chauhan, P.; Deckers, K.; Hermann, G. N.; Mertens, L.; Raabe, G.; Enders, D. Org. Lett. 2014, 16, 5188.CrossRefGoogle Scholar
  20. 20.
    Xia, A.-B.; Zhang, X.-L.; Tang, C.-K.; Feng, K.-X.; Du, X.-H.; Xu, D.-Q. Org. Biomol. Chem. 2017,15, 5709.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Pharmacy – Pharmaceutical SciencesUniversity of Bari Aldo MoroBariItaly

Personalised recommendations