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Synthesis of chromenoimidazocarbolines by a reaction of quaternary iminium salts with o-hydroxybenzaldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

It was shown that the interaction of N 2-(cyanomethyl)-β-carbolinium bromide with o-hydroxybenzaldehydes in the presence of ammonium acetate upon refluxing in ethanol proceeded as a domino reaction and led to the formation of chromenoimidazocarbolines.

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References

  1. (a) Zhang, X.-F.; Sun, R.-Q.; Jia, Y.-F.; Chen, Q.; Tu, R.-F.; Li, K.-K.; Zhang, X.-D.; Du, R.-L.; Cao, R.-H. Sci. Rep. 2016, 6, 33204. (b) Xu, Q.-B.; Chen, X.-F.; Feng, J.; Miao, J.-F.; Liu, J.; Liu, F.-T.; Niu, B.-X.; Cai, J.-Y.; Huang, C.; Zhang, Y.; Ling, Y. Sci. Rep. 2016, 6, 36238. (c) Du, H.; Gu, H.; Li, N.; Wang, J. Med. Chem. Commun. 2016, 7, 636. (d) Salehi, P.; Babanezhad-Harikandei, K.; Bararjanian, M.; Al-Harrasi, A.; Esmaeili, M.-A.; Aliahmadi, A. Med. Chem. Res. 2016, 25, 1895. (e) Shankaraiah, N.; Jadala, C.; Nekkanti, S.; Senwar, K. R.; Nagesh, N.; Shrivastava, S.; Naidu, V. G. M.; Sathish, M.; Kamal, A. Bioorg. Chem. 2016, 64, 42.

  2. Lima, C. F.; Costa, M.; Proença, M. F.; Pereira-Wilson, C. Eur. J. Pharm. Sci. 2015, 72, 34.

    Article  CAS  Google Scholar 

  3. (a) Beryozkina, T. V.; Kolos, N. N.; Bakulev, V. A. Chem. Heterocycl. Compd. 2016, 52, 651. [Khim. Geterotsikl. Soedin. 2016, 52, 651.] (b) Bharate, J. B.; Vishwakarma, R. A.; Bharate, S. B. RSC Adv. 2015, 5, 42020. (c) Sharma, U. K.; Sharma, N.; Vachhani, D.; van der Eycken, E. V. Chem. Soc. Rev. 2015, 44, 1836.

  4. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998, p. 30.

    Google Scholar 

  5. Voskressensky, L. G.; Festa, A. A.; Sokolova, E. A.; Varlamov, A. V. Tetrahedron 2012, 68, 5498.

  6. Voskressensky, L. G.; Sokolova, E. A.; Festa, A. A.; Khrustalev, V. N.; Tuyen, N. V.; Anh, L. T.; Varlamov, A. V. Chem. Heterocycl. Compd. 2013, 49, 484. [Khim. Geterotsikl. Soedin. 2013, 519.]

  7. Voskressensky, L. G.; Festa, A. A.; Sokolova, E. A.; Khrustalev, V. N.; Varlamov, A. V. Eur. J. Org. Chem. 2012, 31, 6124.

    Article  Google Scholar 

  8. Voskressensky, L. G.; Storozhenko, O. A.; Festa, A. A.; Khrustalev, V. N.; Dang, T. T. A.; Nguyen, V. T.; Varlamov, A. V. Tetrahedron Lett. 2015, 56, 6475.

    Article  CAS  Google Scholar 

  9. Kolundžić, F.; Murali, A.; Pérez-Galán, P.; Bauer, J. O.; Strohmann, C.; Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2014, 53, 8122.

  10. (a) Proença, M. F.; Costa, M. Tetrahedron 2010, 66, 4542. (b) Voskressensky, L. G.; Festa, A. A.; Storozhenko, O. A.; Le, A. T.; Nguyen, V. T.; Varlamov, A. V. RSC Adv. 2015, 5, 12442.

  11. Proença, F.; Costa, M. Tetrahedron 2011, 67, 1071.

    Article  Google Scholar 

  12. Costa, M.; Proença, M. F. Tetrahedron 2011, 67, 8622.

    Article  CAS  Google Scholar 

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This work was performed with financial support from the Ministry of Education and Science of the Russian Federation (the program to improve the competitiveness of People's Friendship University of Russia among the world's leading research and education centers in 2016–2020), Russian Foundation for Basic Research (grant 16-53-540004 Viet_a), and Vietnam National Foundation for Science and Technology Development (NAFOSTED).

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Correspondence to Leonid G. Voskressensky.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 501–503

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Voskressensky, L.G., Dao, N.T., Li, T.A. et al. Synthesis of chromenoimidazocarbolines by a reaction of quaternary iminium salts with o-hydroxybenzaldehydes. Chem Heterocycl Comp 53, 501–503 (2017). https://doi.org/10.1007/s10593-017-2083-z

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  • DOI: https://doi.org/10.1007/s10593-017-2083-z

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