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Synthesis and properties of 5-methylidene-3,5-dihydro-4H-imidazol-4-ones (microreview)

  • HETEROCYCLES IN FOCUS
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Chemistry of Heterocyclic Compounds Aims and scope

This microreview presents the key methods of synthesis of 5-methylidene-3,5-dihydro-4H-imidazol-4-ones together with analysis of the relative efficiency for the substituent introduction at different positions of the ring. Also, examples of reactions typical for these compounds presented in the literature over the last seven years are given.

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References

  1. (a) Baranov, M. S.; Lukyanov, K. A; Yampolsky, I. V. Russ. J. Bioorg. Chem. 2013, 3, 223. (b) Walker, C. L.; Lukyanov, K. A.; Yampolsky, I. V.; Mishin, A. S.; Duraj-Thatte, A. M.; Bahareh, Azizi; Tolbert, L. M.; Solntsev, K. M. Curr. Opin. Chem. Biol. 2015, 27, 64.

  2. (a) Khalifa, M. A.; Baset, M. A.; El-Eraky, W. Med. Chem. Res. 2012, 21, 4447. (b) Sadula, A.; Peddaboina, U. R.; Subhashini, P. N. J. Med. Chem. Res. 2015, 24, 851. (c) Dube, P. N.; Mokale, S. N.; Shaikh, S. I.; Patil, Y.; Yadav, B.; Deshmukh, P.; Sabde, S. Pharm. Chem. J. 2015, 49, 125. (d) Youssef, A. S. A.; Kandeel, K. A.; Abou-Elmagd, W. S. I.; Haneen, D. S. A. J. Heterocycl. Chem. 2016, 1, 175.

  3. (a) Baranov, M. S.; Lukyanov, K. A.; Borissova, A. O.; Shamir, J.; Kosenkov, D.; Slipchenko, L. V.; Tolbert, L. M.; Yampolsky, I. V.; Solntsev, K. M. J. Am. Chem. Soc. 2012, 134, 6025. (b) Dong, J.; Solntsev, K. M.; Tolbert, L. M. J. Am. Chem. Soc. 2009, 131, 662.

  4. (a) Paige, J. S.; Wu, K.Y.; Jaffrey, S. R. Science 2011, 333, 642. (b) Han, K. Y.; Leslie, B. J.; Fei, J.; Zhang, J.; Ha, T. J. Am. Chem. Soc. 2013, 135, 19033.

  5. Lee, C.; Chen, Y.; Lin, H.; Jhong, Y.; Chang, C.; Tsai, C.; Kao, C.; Chien, T. Tetrahedron 2012, 68, 5898.

    Article  CAS  Google Scholar 

  6. Baranov, M. S.; Fedyakina, I. T.; Shchelkanov, M. Y.; Yampolsky, I. V. Tetrahedron 2014, 70, 3714.

    Article  CAS  Google Scholar 

  7. (a) Desai, N. C.; Joshi, V. V.; Rajpara, K. M.; Vaghani, H. V.; Satodiya, H. M. Med. Chem. Res. 2013, 22, 1893. (b) Dhingra, A. K.; Chopra, B.; Dass, R.; Mittal, S. K. Chin. Chem. Lett. 2016, 5, 707.

  8. (a) Ivashkin, P. E.; Lukyanov, K. A.; Lukyanov, S.; Yampolsky, I. V. J. Org. Chem. 2011, 8, 2782. (b) Muselli, M.; Baudequin, C.; Perrio, C.; Hoarau, C.; Bischoff, L. Chem.–Eur. J. 2016, 16, 5520.

  9. Baldridge, A.; Kowalik, J.; Tolbert, L. M. Synthesis 2010, 2424.

  10. (a) Baranov, M. S.; Solntsev, K. M.; Baleeva, N. S.; Mishin, A. S.; Lukyanov, S. A.; Lukyanov, K. A.; Yampolsky, I. V. Chem.– Eur. J. 2014, 20, 13234. (b) Ghodbane, A.; Fellows, W. B.; Bright, J. R.; Ghosh, D.; Saffon, N.; Tolbert, L. M.; Fery-Forgues, S.; Solntsev, K. M. J. Mater. Chem. C 2016, 14, 2793. (c) Deng, H.; Su, Y.; Hu, M.; Jin, X.; He, L.; Pang, Y.; Dong, R.; Zhu, X. Macromolecules 2015, 48, 5969.

  11. (a) Hsu, Y.-H.; Chen, Y.-A.; Tseng, H.-W.; Zhang, Z.; Shen, J.-Y.; Chuang, W.-T.; Lin, T.-C.; Lee, C.-S.; Hung, W.-Y.; Hong, B.-C.; Liu, S.-H.; Chou, P.-T. J. Am. Chem. Soc. 2014, 136, 11805. (b) Shen, X.; Huang, G.; Li, K.; Zhang, G.; Zhang, D. Sci. Sin.: Chim. 2013, 43, 1205.

  12. (a) Baranov, M. S.; Solntsev, K. M.; Lukyanov, K. A.; Yampolsky, I. V. Chem. Commun. 2013, 49, 5778. (b) Wang, Y.; Xie, H.; Pan, Y.-R.; Ding, M.-W. Synthesis 2014, 46, 336.

  13. Gong, X.; Yang, H.; Liu, H.; Jiang, Y.; Zhao, Y.; Fu, H. Org. Lett. 2010, 12, 3128.

    Article  CAS  Google Scholar 

  14. Gabillet, S.; Loreau, O.; Specklin, S.; Rasalofonjatovo, E.; Taran, F. J. Org. Chem. 2014, 79, 9894.

    Article  CAS  Google Scholar 

  15. Gosling, S.; Rollin, P.; Tatibouët, A. Synthesis 2011, 3649.

  16. Ikejiri, M.; Tsuchino, M.; Chihara, Y.; Yamaguchi, T.; Imanishi, T.; Obika, S.; Miyashita, K. Org. Lett. 2012, 17, 4406.

    Article  Google Scholar 

  17. Walker, C. L.; Lukyanov, K. A.; Yampolsky, I. V.; Mishin, A. S.; Bommarius, A. S.; Duraj-Thatte, A. M.; Azizi, B.; Tolbert, L. M.; Solntsev, K. M. Curr. Opin. Chem. Biol. 2015, 27, 64.

    Article  CAS  Google Scholar 

  18. Huang, G.-J.; Ho, J.-H.; Prabhakar, C.; Liu, Y.-H.; Peng, S.-M.; Yang, J.-S. Org. Lett. 2012, 12, 5034.

    Article  Google Scholar 

  19. Golodukhina, S. V.; Baleeva, N. S.; Mineyev, K. S.; Baranov, M. S. Chem. Heterocycl. Compd. 2015, 51, 944. [Khim. Heterocycl. Soedin. 2015, 51, 945.]

  20. Abdel-Rahman, R. M.; Makki, M. S. I. T.; Bawazir, W. A. E–J. Chem. 2011, 8, 405.

    CAS  Google Scholar 

  21. Miqdad, O. A.; Abunada, N. M.; Hassaneen, H. M. Heteroat. Chem. 2011, 22, 131.

    Article  CAS  Google Scholar 

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This work was supported by the Russian Foundation for Basic Research (grant 15-33-20518_mol_a_ved).

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Correspondence to Mikhail S. Baranov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 444–446

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Baleeva, N.S., Baranov, M.S. Synthesis and properties of 5-methylidene-3,5-dihydro-4H-imidazol-4-ones (microreview). Chem Heterocycl Comp 52, 444–446 (2016). https://doi.org/10.1007/s10593-016-1909-4

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  • DOI: https://doi.org/10.1007/s10593-016-1909-4

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