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Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2Н-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers

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Chemistry of Heterocyclic Compounds Aims and scope

Enamines of acetoacetic ester and acetylacetone added at the activated double bond of 2-R1-3-nitro-2Н-chromenes (R1 = CF3, CCl3, Ph) with their central α-С atoms, forming trans,trans-2,3,4-trisubstituted chromans. The adducts obtained from acetylacetone enamines represented mixtures of comparable amounts of configurationally stable atropisomers, the formation of which was connected with hindered rotation around the C(sp 3)–C(sp 2) bond. A reaction with enamines of acetoacetic ester led practically exclusively to a single anti atropisomer.

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Scheme 1
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References

  1. (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893. (b) Bergmann, R.; Gericke, R. J. Med. Chem. 1990, 33, 492. (c) Burrell, G.; Cassidy, F.; Evans, J. M.; Lightowler, D.; Stemp, G. J. Med. Chem. 1990, 33, 3023. (d) Gericke, R.; Harting, J.; Lues, I.; Schittenhelm, C. J. Med. Chem.1991, 34, 3074.

  2. Murugesh, M. G.; Subburaj, K.; Trivedi, G. K. Tetrahedron 1996, 52, 2217.

    Article  CAS  Google Scholar 

  3. (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. Beilst. J. Org. Chem. 2012, 8, 1668.

  4. Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Barkov, A. Yu. Russ. Chem. Rev. 2013, 82, 1081. [Usp. Khim. 2013, 82, 1081.]

  5. (a) 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.] (b) 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. (c) 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.

  6. (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.]

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

    Article  CAS  Google Scholar 

  8. Korotaev, V. Yu.; Kutyashev, I. B.; Barkov, A. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2015, 51, 440. [Khim. Geterotsikl. Soedin. 2015, 51, 440.]

  9. Tulinsky, J.; Cheney, B. V.; Mizsak, S. A.; Watt, W.; Han, F.; Dolak, L. A.; Judge, T.; Gammill, R. B. J. Org. Chem. 1999, 64, 93.

    Article  CAS  Google Scholar 

  10. Sawadjoon, S.; Kittakoop, P.; Kirtikara, K.; Vichai, V.; Tanticharoen, M.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 5470.

    Article  CAS  Google Scholar 

  11. (a) Saito, A.; Nakajima, N.; Tanaka, A.; Ubukata, M. Tetrahedron 2002, 58, 7829. (b) Rithner, C. D.; Bushweller, C. H.; Gensler, W. J.; Hoogasian, S. J. Org. Chem. 1983, 48, 1491. (c) Selenski, C.; Pettus, T. R. R. Tetrahedron 2006, 62, 5298. (d) Kloser, E.; Böhmdorfer, S.; Brecker, L.; Kählig, H.; Netscher, T.; Mereiter, K.; Rosenau, T. Eur. J. Org. Chem. 2011, 2450.

  12. (a) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Kutyashev, I. B. Russ. Chem. Bull., Int. Ed. 2007, 56, 2054 [Izv. Akad. Nauk, Ser. Khim. 2007, 1985.] (b) Habib, P. M.; Kavala, V.; Rama Raju, B.; Kuo,C.-W.; Huang, W.-C.; Yao, C.-F. Eur. J. Org. Chem. 2009, 4503. (c) Lin, C.; Hsu, J.; Sastry, M. N. V.; Fang, H.; Tu, Z.; Liu, J.-T.; Ching-Fa, Y. Tetrahedron 2005, 61, 11751.

  13. (a) Saito, K.; Yamamoto, M.; Yamada, K. Tetrahedron 1993, 49, 4549. (b) Kessler, H. Angew. Chem., Int. Ed. 1970, 9, 219.

  14. (a) Ōki, M. Acc. Chem. Res. 1984, 17, 154. (b) Lomas, J. S.; Dubois, J.-E. Tetrahedron 1978, 34, 1597. (c) Chupp, J. P.; Olin, J. F. J. Org. Chem. 1967, 32, 2297.

  15. Hallé, J.-C.; Vichard, D.; Pouet, M.-J.; Terrier, F. J. Org. Chem. 1997, 62, 7178.

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  Google Scholar 

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

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Correspondence to Vyacheslav Ya. Sosnovskikh.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(6), 531–540

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Korotaev, V.Y., Barkov, A.Y., Ezhikova, M.A. et al. Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2Н-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers. Chem Heterocycl Comp 51, 531–540 (2015). https://doi.org/10.1007/s10593-015-1733-2

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