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Complementary pairing of o-quinone methides with 3-(N,N-diethylamino)acrolein – synthesis of 1H-benzo[f]chromene-2-carbaldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

A Correction to this article was published on 01 August 2017

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A series of 1H-benzo[f]chromene-2-carbaldehydes was obtained from naphthol Mannich bases and 3-(N,N-diethylamino)acrolein via a cascade reaction comprising [4+2] cycloaddition of generated in situ 1,2-naphthoquinone-2-methides and a push-pull β-enaminoaldehyde with consecutive elimination of diethylamine.

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  • 05 October 2017

    A correction to this article has been published.

References

  1. Ishar, M. P. S.; Singh, G.; Singh, S.; Sreenivasan, K. K.; Singh, G. Bioorg. Med. Chem. Lett. 2006, 16, 1366.

    Article  CAS  Google Scholar 

  2. Galal, S. A.; Abd El-All, A. S.; Abdallah, M. M.; El-Diwani, H. I. Bioorg. Med. Chem. Lett. 2009, 19, 2420.

    Article  CAS  Google Scholar 

  3. Legoabe, L. J.; Petzer, A.; Petzer, J. P. Bioorg. Med. Chem. Lett. 2012, 22, 5480.

    Article  CAS  Google Scholar 

  4. (a) Shim, Y. S.; Kim, K. C.; Chi, D. Y.; Lee, K.-H.; Cho, H. Bioorg. Med. Chem. Lett. 2003, 13, 2561. (b) Shim, Y. S.; Kim, K. C.; Lee, K. A.; Shrestha, S.; Lee, K.-H.; Kim, C. K.; Cho, H. Bioorg. Med. Chem. 2005, 13, 1325.

  5. Alemán, J.; Núñez, A.; Marzo, L.; Marcos, V.; Alvarado, C.; Ruano, J. L. G. Chem.–Eur. J. 2010, 16, 9453.

  6. Alemán, J.; Alvarado, C.; Marcos, V.; Núñez, A.; Ruano, J. L. G. Synthesis 2011, 1840.

  7. (a) Rueping, M.; Dufour, J.; Maji, M. S. Chem. Commun. 2012, 48, 3406. (b) Zhang, X.; Zhang, S.; Wang, W. Angew. Chem., Int. Ed. 2010, 49, 1481.

  8. (a) Reynolds, G. A.; Van Allan, J. A. J. Org. Chem. 1971, 36, 600. (b) Koblik, A. V.; Suzdalev, K. F. J. Org. Chem. USSR 1989, 25, 155. [Zh. Org. Khim. 1989, 25, 171.]

  9. René, L. Synthesis 1989, 69.

  10. Balasubramanian, K. K.; Selvaraj, S. Tetrahedron Lett. 1980, 21, 851.

    Article  CAS  Google Scholar 

  11. (a) Van De Water, R. W.; Pettus, T. R. R. Tetrahedron 2002, 58, 5367. (b) Ferreira, S. B.; da Silva, F. C.; Pinto, A. C.; Gonzaga, D. T. G.; Ferreira, V. F. J. Heterocycl. Chem. 2009, 46, 1080.

  12. (a) Wojciechowski, K.; Dolatowska, K. Tetrahedron 2005, 61, 8419. (b) Chauhan, M. S.; Dean, F. M.; Matkin, D.; Robinson, M. L. J. Chem. Soc., Perkin Trans. 1 1973, 120. (c) Chen, W.; Park, S. K.; Yu, W.; Xiong, A.; Sanders, B. G.; Kline, K. Eur. J. Med. Chem. 2012, 58, 72. (d) Wang, H.; Wang, Y.; Han, K.-L.; Peng, X.-J. J. Org. Chem. 2005, 70, 4910.

  13. (a) Osyanin, V. A.; Ivleva, E. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2011, 47, 845. [Khimiya geterotsikl. soedinenii 2011, 1032.] (b) Osyanin, V. A.; Ivleva, E. A.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2012, 48, 795. [Khim. Geterotsikl. Soedin. 2012, 855.]

  14. Osyanin, V. A.; Lukashenko, A. V.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2015, 50, 1528. [Khim. Geterotsikl. Soedin. 2014, 1663.]

  15. Osyanin, V. A.; Ivleva, E. A.; Klimochkin, Y. N. Synth. Commun. 2012, 42, 1832.

    Article  CAS  Google Scholar 

  16. Osyanin, V. A.; Osipov, D. V.; Pavlov, S. A.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2014, 50, 1195 [Khim. Geterotsikl. Soedin. 2014, 1293.]

  17. Osyanin, V. A.; Dr. Chem. Thesis; Samara, 2014. [http://d21221705.samgtu.ru/sites/d21221705.samgtu.ru/files/osyaninv.pdf]

  18. (a) Samarakoon, T.; Hur, M. Y.; Kurtz, R. D.; Hanson, P. R. Org. Lett. 2010, 12, 2182. (b) Babaev, E. V. Chem. Heterocycl. Compd. 1993, 29, 796. [Khim. Geterotsikl. Soedin. 1993, 937.] (c) Osipov D. V. PhD Chem. Thesis; Samara, 2014. [http://d21221705.samgtu.ru/sites/d21221705.samgtu.ru/files/dissertaciya_osipovdv.pdf]

  19. (a) Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Russ. J. Org. Chem. 2013, 49, 398. [Zh. Org. Khim. 2013, 49, 412]. (b) Littman, J. B.; Brode, W. R. J. Am. Chem. Soc. 1930, 52, 1655. (c) Snyder, H. R.; Brewster, J. H. J. Am. Chem. Soc. 1948, 70, 4230. (d) Elokdah, H.; McFarlane, G.; Mayer, S.; Crandall, D. US Patent 2003018067.

  20. Pasedach, H.; Seefelder, M.; Spaenig, H.; Weickmann, A. US Patent 2808437.

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This work was supported by the Ministry of Education and Science of the Russian Federation (agreement № 14.574.21.0120, the unique identifier RFMEFI57414X0120).

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Correspondence to Vitaly A. Osyanin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(9), 711–715

A correction to this article is available online at https://doi.org/10.1007/s10593-017-2150-5.

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Lukashenko, A.V., Osyanin, V.A., Osipov, D.V. et al. Complementary pairing of o-quinone methides with 3-(N,N-diethylamino)acrolein – synthesis of 1H-benzo[f]chromene-2-carbaldehydes. Chem Heterocycl Comp 52, 711–715 (2016). https://doi.org/10.1007/s10593-016-1941-4

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