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Synthesis of Pyrrolo[2,1-c][1,4]oxazine-1,6,7-triones by the Reaction of 3-Methylenemorpholin-2-ones with Oxalyl Chloride

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Abstract

(Z)-3-(2-Aryl-2-oxoethylidene)morpholin-2-ones were synthesized by the reaction of aroylpyruvic acids with ethanolamine or 2-propanolamine. The products reacted with oxalyl chloride to form 8-aroyl-3,4-dihydropyrrolo[2,1-c][1,4]oxazin-1,6,7(1H)-triones.

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Notes

  1. For preliminary communication, see [18].

REFERENCES

  1. Maslivets, A.N., Mashevskaya, I.V., Krasnykh, O.P., Shurov, S.N., and Andreichikov, Y.S., Zh. Org. Khim., 1992, vol. 28, p. 2545.

    Google Scholar 

  2. Aliev, Z.G., Krasnykh, O.P., Maslivets, A.N., and Atovmyan, L.O., Izv. Akad. Nauk, Ser. Khim., 2000, vol. 12, p. 2080.

    Google Scholar 

  3. Maslivets, A.N., Golovnina, O.V., Krasnykh, O.P., and Aliev, Z.G., Chem. Heterocycl. Compd., 2000, vol. 36, p. 105. https://doi.org/10.1007/BF02256855

    Article  CAS  Google Scholar 

  4. Tolmacheva, I.A., Mashevskaya, I.V., and Maslivets, A.N., Russ. J. Org. Chem., 2001, vol. 37, p. 596. https://doi.org/10.1023/A:1012458608681

    Article  CAS  Google Scholar 

  5. Mashevskaya, I.V., Makhmudov, R.R., Aleksandrova, G.A., Golovnina, O.V., Duvalov, A.V., and Maslivets, A.N., Khim.-Farm. Zh., 2001, vol. 35, p. 20.

    Google Scholar 

  6. Tolmacheva, I.A., Mashevskaya, I.V., and Maslivets, A.N., Russ. J. Org. Chem., 2002, vol. 38, p. 281. https://doi.org/10.1023/A:1015590306099

    Article  CAS  Google Scholar 

  7. Maslivets, A.N., Mashevskaya, I.V., Duvalov, A.V., Kol’tsova, S.V., and Feshin, V.P., Russ. J. Org. Chem., 2002, vol. 38, p. 738. https://doi.org/10.1023/A:1019679526434

    Article  CAS  Google Scholar 

  8. Aliev, Z.G., Maslivets, A.N., Golovnina, O.V., Krasnykh, O.P., Atovmyan, L.O., Zh. Strukt. Khim., 2002, vol. 43, p. 576.

    Google Scholar 

  9. Kistanova, N.S., Mashevskaya, I.V., Bozdyreva, K.S., and Maslivets, A.N., Chem. Heterocycl. Compd., 2003, vol. 39, p. 673. https://doi.org/10.1023/A:1025170821406

    Article  CAS  Google Scholar 

  10. Vostrov, E.S., Gilev, D.V., and Maslivets, A.N., Chem. Heterocycl. Compd., 2004, vol. 40, p. 532. https://doi.org/10.1023/B:COHC.0000033556.58356.5c

    Article  CAS  Google Scholar 

  11. Bozdyreva, K.S., Smirnova, I.V., and Maslivets, A.N., Russ. J. Org. Chem., 2005, vol. 41, p. 1081. https://doi.org/10.1007/s11178-005-0296-6

    Article  CAS  Google Scholar 

  12. Semenova, T.D. and Krasnykh, O.P., Russ. J. Org. Chem., 2005, vol. 41, p. 1222. https://doi.org/10.1007/s11178-005-0321-9

    Article  CAS  Google Scholar 

  13. Chervyakov, A.V. and Maslivets, A.N., Russ. J. Org. Chem., 2013, vol. 49, p. 943. https://doi.org/10.1134/S1070428013060286

    Article  CAS  Google Scholar 

  14. Maslivets, A.N., Lisovenko, N.Yu., Golovnina, O.V., Vostrov, E.S., and Tarasova, O.P., Chem. Heterocycl. Compd., 2000, vol. 36, p. 483. https://doi.org/10.1007/BF02269553

    Article  CAS  Google Scholar 

  15. Silaichev, P.S., Kryuchkova, M.A., and Maslivets, A.N., Russ. J. Org. Chem., 2009, vol. 45, p. 1730. https://doi.org/10.1134/S1070428009110293

    Article  CAS  Google Scholar 

  16. Andreichikov, Yu.S., Voronova, L.A., Astaf’eva, I.Yu., Tendryakova, S.V., and Belykh, Z.D., USSR Inventor’s Certificate no. 621676, 1978.

  17. Maslivets, A.N. and Mashevskaya, I.V., 2,3-Digidro-2,3-pirroldiony (2,3-Dihydropyrrol-2,3-diones), Perm: Perm. Gos. Univ., 2005.

  18. Tretyakov, N.A., Shavrina, T.V., and Maslivets, A.N., Russ. J. Org. Chem., 2019, vol. 55, p. 719. https://doi.org/10.1134/S1070428019050221

    Article  CAS  Google Scholar 

  19. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, S1. https://doi.org/10.1039/P298700000S1

  20. CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET).

  21. Sheldrick, G.M., Acta Crystallogr. Sect. A., 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930

    Article  CAS  Google Scholar 

  22. Sheldrick, G.M., Acta Crystallogr. Sect. C., 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  23. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K., and Puschmann, H., J. Appl. Cryst., 2009, vol. 42, p. 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 19-33-90222) and the Government of the Perm Krai.

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Authors and Affiliations

  1. Perm State University, 614990, Perm, Russia

    N. A. Tret’yakov, M. V. Dmitriev & A. N. Maslivets

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  1. N. A. Tret’yakov
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Correspondence to A. N. Maslivets.

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Tret’yakov, N.A., Dmitriev, M.V. & Maslivets, A.N. Synthesis of Pyrrolo[2,1-c][1,4]oxazine-1,6,7-triones by the Reaction of 3-Methylenemorpholin-2-ones with Oxalyl Chloride. Russ J Org Chem 56, 1367–1373 (2020). https://doi.org/10.1134/S1070428020080060

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