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Stereoselective addition of ethyl 3-morpholino(piperidino)-crotonates to 2-trihalomethyl-3-nitro-2H-chromenes. Synthesis of 4-acetonyl-3-nitrochromans

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Chemistry of Heterocyclic Compounds Aims and scope

Tertiary enamines of acetoacetic ester, obtained with morpholine and piperidine, add to 2-R1-3-nitro-2Н-chromenes (R1 = CF3, CCl3, Ph) via the vinylogue β-methyl group and give the respective cis,trans-2,3,4-trisubstituted chromans, the stereoconfiguration of which was established by X-ray structural analysis. Acidic hydrolysis of these compounds was accompanied by decarboxylation and produced 4-acetonyl-3-nitrochromans with retention of configuration.

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References

  1. (a) Paul, N. D.; Mandal, S.; Otte, M.; Cui, X.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2014, 136, 1090. (b) Majumdar, N.; Paul, N. D.; Mandal, S.; de Bruin, B.; Wulff, W. D. ACS Catal. 2015, 5, 2329. (c) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. (d) Bergmann, R.; Gericke, R. J. Med. Chem. 1990, 33, 492. (e) Burrell, G.; Cassidy, F.; Evans, J. M.; Lightowler, D.; Stemp, G. J. Med. Chem. 1990, 33, 3023. (f) Gericke, R.; Harting, J.; Lues, I.; Schittenhelm, C. J. Med. Chem. 1991, 34, 3074.

  2. (a) Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001. (b) Yoshikoshi, A.; Miyashita, M. Acc. Chem. Res. 1985, 18, 284. (c) Bhanja, C.; Jena, S.; Nayak, S.; Mohapatra, S. Beilstein J. Org. Chem. 2012, 8, 1668. (d) Zhang, D.; Ma, Y.; Liu, Y.; Liu, Z.-P. Arch. Pharm. 2014, 347, 576.

  3. Korotaev, V. Yu.; Kutyashev, I. B.; Sosnovskikh, V. Ya. Heteroat. Chem. 2005, 16, 492.

    Article  CAS  Google Scholar 

  4. (a) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Barkov, A. Yu. Russ. Chem. Rev. 2013, 82, 1081. [Usp. Khim. 2013, 82, 1081.] (b) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Kutyashev, I. B.; Kodess, M. I. Russ. Chem. Bull., Int. Ed. 2006, 55, 2020. [Izv. Akad. Nauk, Ser. Khim. 2006, 1945.] (c) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Kutyashev, I. B. Russ. Chem. Bull., Int. Ed. 2007, 56, 2054. [Izv. Akad. Nauk, Ser. Khim. 2007, 1985.] (d) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Barabanov, M. A.; Yasnova, E. S.; Ezhikova, M. A.; Kodess, M. I.; Slepukhin, P. A. Tetrahedron 2010, 66, 1404. (e) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Barkov, A. Yu.; Slepukhin, P. A.; Ezhikova, M. A.; Kodess, M. I.; Shklyaev, Yu. V. Tetrahedron 2011, 67, 8685.

  5. Gupta, R. C.; Seth, M.; Bhaduri, A. P. Indian J. Chem. 1991, 30B, 297.

    CAS  Google Scholar 

  6. Korotaev, V. Yu.; Barkov, A. Yu.; Sokovnina, A. A.; Sosnovskikh, V. Ya. Mendeleev Commun. 2013, 23, 150.

    Article  CAS  Google Scholar 

  7. (a) Korotaev, V. Yu.; Barkov, A. Yu.; Sosnovskikh, V. Ya. Tetrahedron Lett. 2013, 54, 3091. (b) Korotaev, V. Yu.; Barkov, A. Yu.; Kutyashev, I. B.; Kotovich, I. V.; Ezhikova, M. A.; Kodess, M. I.; Sosnovskikh, V. Ya. Tetrahedron 2015, 71, 2658.

  8. Kostyuk, A. N.; Volochnyuk, D. M.; Sibgatulin, D. A. Synthesis 2008, 161.

  9. (a) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Kutyashev, I. B.; Kodess, M. I. Lett. Org. Chem. 2005, 2, 616. (b) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Kutyashev, I. B.; Kodess, M. I. Russ. Chem. Bull., Int. Ed. 2006, 55, 317. [Izv. Akad. Nauk, Ser. Khim. 2006, 309.]

  10. Korotaev, V. Yu.; Barkov, A. Yu.; Slepukhin, P. A.; Kodess, M. I.; Sosnovskikh, V. Ya. Tetrahedron Lett. 2011, 52, 5764.

    Article  CAS  Google Scholar 

  11. Wang, P.-A.; Zhang, D.-X.; Liu, X.-Y. ARKIVOC 2014, (v), 408.

  12. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

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The results of this work were obtained within the framework of fulfilling the State Assignment of the Ministry of Education and Science of Russia, with partial financial support from the Russian Foundation for Basic Research (project No. 14-03-00179).

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Authors and Affiliations

  1. Institute of Natural Sciences, Ural Federal University named after first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg, 620000, Russia

    Vladislav Yu. Korotaev, Igor B. Kutyashev, Alexey Yu. Barkov & Vyacheslav Ya. Sosnovskikh

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  1. Vladislav Yu. Korotaev
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  2. Igor B. Kutyashev
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  3. Alexey Yu. Barkov
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  4. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vyacheslav Ya. Sosnovskikh.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(5), 440–446

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Korotaev, V.Y., Kutyashev, I.B., Barkov, A.Y. et al. Stereoselective addition of ethyl 3-morpholino(piperidino)-crotonates to 2-trihalomethyl-3-nitro-2H-chromenes. Synthesis of 4-acetonyl-3-nitrochromans. Chem Heterocycl Comp 51, 440–446 (2015). https://doi.org/10.1007/s10593-015-1718-1

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