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Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers

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Abstract

The Biginelli reaction between 5-R-salicylic aldehyde (R = H, Me, and Br), α-nitroacetophenone, and urea affords 8-R-11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo-[g][1,3,5]oxadiazocin-4(3Н)-ones as mixtures of two diastereomers. The ratio of diastereomers depends on the catalyst (HCl) concentration in the reaction medium. In DMSO and DMF, the resulting compounds undergo oxadiazocine ring opening with establishment of a three-component equilibrium between 4-(2-hydroxy-5-R-phenyl)-5-nitro-6-phenyl-3,4-dihydropyrimidin-2(1Н)-one as the major component and diastereomeric methanobenzoxadiazocines as two minor components. Dilution of these solutions with water favors the oxa-Michael reaction resulting in the reverse transformation of dihydropyrimidinones into the corresponding starting diastereomers.

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References

  1. C. O. Kappe, in Multicomponent Reactions, Eds J. Zhu, H. Bienayme, Wiley-VCH, 2005, p. 95–120.

  2. K. Singh, K. Singh, Adv. Heterocycl. Chem., 2012, 105, 223–308.

    Article  CAS  Google Scholar 

  3. S. V. Vdovina, V. A. Mamedov, Russ. Chem. Rev., 2008, 77, 1017.

    Article  CAS  Google Scholar 

  4. J. S. Sandhu, ARKIVOC, 2012, Part i, 66.

    Google Scholar 

  5. G. Ya. Remennikov, Chem. Heterocycl. Compd. (Engl. Transl.), 1997, 33, 1369 [Khim. Heterocycl. Soedin., 1997, 1587].

    Article  CAS  Google Scholar 

  6. V. F. Sedova, T. V. Voevoda, T. G. Tolstikova, O. P. Shkurko, Pharm. Chem. J. (Engl. Transl.), 2002, 36, 284 [Khim.-Farm. Zh., 2002, 36, No. 6, 4].

    Article  CAS  Google Scholar 

  7. Z. D. Dubovenko, V. P. Mamaev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1972, No. 3, 101 [Chem. Abstrs, 1972, 77, 152097].

    Google Scholar 

  8. C. O. Kappe, Eur. J. Med. Chem., 2000, 35, 1043.

    Article  CAS  Google Scholar 

  9. G. Ya. Remennikov, C. C. Shavaran, I. V. Boldirev, L. K. Kurilenko, B. M. Klebanov, V. P. Kuchar, Pharm. Chem. J. (Engl. Transl.), 1991, 25, 185 [Khim.-Farm. Zh., 1991, 25, No. 3, 35].

    Article  Google Scholar 

  10. L. Heys, C. G. Moor, P. J. Murphy, Chem. Soc. Rev., 2000, 29, 57.

    Article  CAS  Google Scholar 

  11. K. Singh, D. Arora, K. Singh, S. Singh, Mini-Rev. Med. Chem., 2009, 9, 95.

    Article  CAS  Google Scholar 

  12. A. O. Bryzgalov, M. P. Dolgikh, I. V. Sorokina, T. G. Tolstikova, V. F. Sedova, O. P. Shkurko, Bioorg. Med. Chem. Lett., 2006, 16, 1418.

    Article  CAS  Google Scholar 

  13. M. M. Savant, A. M. Pansuriya, C. V. Bhuva, N. P. Kapuriya, Y. T. Naliapara, Catal. Lett., 2009, 132, 281.

    Article  CAS  Google Scholar 

  14. J. Svetlik, V. Hanus, J. Bella, J. Chem. Res. (S), 1991, 4.

    Google Scholar 

  15. J. Svetlik, L. Veizerova, V. Kettman, Tetrahedron Lett., 2008, 49, 3520.

    Article  CAS  Google Scholar 

  16. D. S. Bose, M. Sudharshan, S. W. Chavhan, ARKIVOC, 2005, Part iii, 228.

    Google Scholar 

  17. N.-Y. Fu, Y.-F. Yuan, Z. Cao, S.-W. Wang, J.-T. Wang, C. Peppe, Tetrahedron, 2002, 58, 4801.

    Article  CAS  Google Scholar 

  18. E. M. H. Abbas, S. M. Abdallah, M. H. Abdjh, H. A. Tawfik, W. S. El-Hamouly, Turk. J. Chem., 2008, 32, 297.

  19. M. M. Kurbanova, Russ. J. Org. Chem. (Engl. Transl.), 2010, 46, 599 [Zh. Org. Khim., 2010, 46, 606].

    Article  CAS  Google Scholar 

  20. Q. Cheng, Q. Wang, X. Xu, M. Ruan, H. Yao, X. Yang, J. Heterocycl. Chem., 2010, 47, 624.

    Article  CAS  Google Scholar 

  21. Q. Liu, J. Xu, F. Teng, A. Chen, N. Pan, W. Zhang, J. Heterocycl. Chem., 2014, 51, 741.

    Article  CAS  Google Scholar 

  22. V. F. Sedova, V. P. Krivopalov, Yu. V. Gatilov, O. P. Shkurko, Mendeleev Commun., 2013, 23, 176.

    Article  CAS  Google Scholar 

  23. V. F. Sedova, V. P. Krivopalov, Yu. V. Gatilov, O. P. Shkurko, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 1378 [Izv. Akad. Nauk, Ser. Khim, 2014, 1378].

    Article  CAS  Google Scholar 

  24. V. F. Sedova, V. P. Krivopalov, O. P. Shkurko, Russ. J. Org. Chem. (Engl. Transl.), 2009, 45, 1535 [Zh. Org. Khim., 2009, 45, 1550].

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrentéva, 630090, Novosibirsk, Russian Federation

    V. F. Sedova, V. P. Krivopalov & O. P. Shkurko

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  1. V. F. Sedova
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  2. V. P. Krivopalov
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  3. O. P. Shkurko
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Correspondence to O. P. Shkurko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0215—0222, January, 2016.

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Sedova, V.F., Krivopalov, V.P. & Shkurko, O.P. Synthesis and intramolecular transformations of 8-substituted 11-nitro-2-phenyl-5,6-dihydro-2H-2,6-methanobenzo[g][1,3,5]oxadiazocin-4(3H)-one diastereomers. Russ Chem Bull 65, 215–222 (2016). https://doi.org/10.1007/s11172-016-1287-1

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  • DOI: https://doi.org/10.1007/s11172-016-1287-1

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