Facile synthesis of heteroaryl substituted -lactams from nitrovinyl arenes

Facile synthesis of heteroaryl substituted -lactams from nitrovinyl arenes

Aliphatic nitroalkanes with different functional groups were synthesized from the Michael addition reactions of active methylene compounds 2 and nitrovinyl arenes 1 in high yields. The synthesized Michael adducts were subjected to intramolecular cyclization to give heteroaryl substituted -lactams in good to high yields under mild reaction conditions.

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  • 1. Caruano, J.; Muccioli, G. G.; Robiette, R. Org. Biomol. Chem . 2016 , 14 , 10134-10156.
  • 2. Park, J. H.; Ahn, C.; Lam, Y. F.; Won, T. J.; Shin, D. S.; Kim, J. A.; Oh, S. J.; Ha, J. R. Tetrahedron Lett . 2005 , 46 , 1755-1757.
  • 3. Ghoari, M. K.; Tiwari, D. P. J. Org. Chem . 2010 , 75 , 6173-6181.
  • 4. Yoon, C. H.; Nagle, A.; Chen, C.; Gandhi, D.; Jung, K. W. Org. Lett . 2003 , 5 , 2259-2262.
  • 5. Deredas, D.; Albrecht, L.; Krawczyk, H. Tetrahedron Lett . 2013 , 54 , 3088-3090.
  • 6. Padwa, A.; Nara, S.; Wang, Q. J. Org. Chem . 2005 , 70 , 8538-8549.
  • 7. Belmar, J.; Funk, R. L. J. Am. Chem. Soc . 2012 , 134 , 16941-16943.
  • 8. Miyabe, H.; Asada, R.; Toyoda, A.; Takemoto, Y. Angew. Chem. Int. Ed . 2006 , 45 , 5863-5866.
  • 9. Ishibashi, H.; Haruki, S.; Uchiyama, M.; Tamurab, O.; Matsuo, J. Tetrahedron Lett . 2006 , 47 , 6263-6266.
  • 10. Okino, T.; Hoashi, Y.; Furukawa, T.; Xu, X.; Takemoto, Y. J. Am. Chem. Soc . 2005 , 127 , 119-125.
  • 11. Barrett, A. G. M.; Spilling, C. D. Tetrahedron Lett . 1988 , 29 , 5733-5734.
  • 12. Kie, F. M.; Poggendorf, P.; Picasso, S.; Jager, V. Chem. Commun . 1988 , 1 , 119-120.
  • 13. Keinan, E.; Mazur, Y. J. Am. Chem. Soc . 1977 , 99 , 3861-3862.
  • 14. McMurry, J. E.; Melton, J.; Padgett, H. J. Org. Chem . 1974 , 39 , 259-260.
  • 15. Shono, T.; Hamaguchi, H.; Mikami, H; Nogusa, H.; Kashimura, S. J. Org. Chem . 1983 , 48 , 2103-2105.
  • 16. Wang, K.; Qian, X.; Cui, J. Tetrahedron 2009 , 65 , 10377-10382.
  • 17. Tu, Z.; Jang, Y.; Lin, C.; Liu, J. T.; Hsu, J.; Sastry, M. N. V.; Yao, C. F. Tetrahedron 2005 , 61 , 10541-20551.
  • 18. Saidi, M. R.; Azizi, N.; Akbari, E.; Ebrahimi, F. J. Mol. Catal. A: Chem . 2008 , 292 , 44-48.
  • 19. Cinar, S.; Unaleroglu, C.; Ak, A.; Garipcan, B. Med. Chem. Res . 2017 , 26 , 1022-1028.
  • 20. Baron, M.; Metay, E.; Lemaire, M; Popowycz, F. Green Chem. 2013 , 15 , 1006-1015.
  • 21. Wang, K.; Qian, X.; Cui, J. Tetrahedron 2009 , 65 , 10377-10382.
  • 22. Basel, Y.; Hassner, A. Synthesis 1997 , 3 , 309-312.
  • 23. Ye, J.; Dixon, D. J.; Hynes, P. S. Chem. Commun . 2005 , 4481-4483.
  • 24. Baron, M.; Metay, E.; Lemaire, M; Popowycz, F. J. Org. Chem . 2012 , 77 , 3598-3603.
  • 25. Naicuk, F. F.; Vargas, D. Z.; D'Oca, C. R. M.; Moro, C. C.; Russowsky, D. New J. Chem. 2015 , 39 , 1643-1653.
  • 26. Aksenov, A. V.; Aksenov, N. A.; Skomorokhov, A. A.; Aksenova, I. V.; Gryaznov, G. D.; Voskressensky, L. G.; Rubin, M. A. Chem. Heterocycl. Compd. 2016 , 52 , 923-927.