Russian Chemical Bulletin

, Volume 61, Issue 8, pp 1640–1642 | Cite as

Synthesis of diaminomethylidene derivatives of tetronic acid

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Abstract

Methyl 4-chloro-3-oxobutanoate reacts with benzoylcyanamide in the presence of catalytic amounts of Ni(acac)2 to give the corresponding ketene N-benzoylaminal, which is transformed in boiling AcOH into 3-[(amino)(benzoylamino)methylidene]tetrahydrofuran-2,4-dione. Debenzoylation of the latter in the presence of EtONa in EtOH yields a N,N-unsubstituted diaminomethylidene derivative of tetronic acid. Cyclization of the adduct of methyl 4-chloro-3-oxobutanoate with benzoylcyanamide in the presence of triethylamine follows a different pathway leading to methyl 2-amino-1-benzoyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate.

Key words

methyl 4-chloro-3-oxobutanoate benzoylcyanamide cyclization diaminomethylidene derivative of tetronic acid 
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References

  1. 1.
    D. Tejedor, F. Garcia-Tellodo, Org. Prep. Proc. Int., 2004, 36, 33.CrossRefGoogle Scholar
  2. 2.
    A. L. Zagrafos, D. Georgiadis, Synthesis, 2006, 3157.Google Scholar
  3. 3.
    R. Schobert, A. Schlenk, Bioorg. Med. Chem., 2008, 16, 4203.CrossRefGoogle Scholar
  4. 4.
    G. Athanasellis, O. Igglesi-Markopoulou, J. Markopoulos, Bioinorg. Chem. Appl., 2010, Article ID 315056.Google Scholar
  5. 5.
    K. Görlitrer, U. Bartke, Pharmazie, 2002, 57, 672.Google Scholar
  6. 6.
    N. Sydorenko, R. P. Hsung, O. S. Darwish, J. M. Hahn, J. Lui, J. Org. Chem., 2004, 69, 6732.CrossRefGoogle Scholar
  7. 7.
    S. A. Savina, V. M. Lyubchanskaya, L. M. Alekseeva, A. S. Shashkov, V. G. Granik, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 2298 [Izv. Akad. Nauk, Ser. Khim., 2007, 2220].CrossRefGoogle Scholar
  8. 8.
    Y. Bourdreux, E. Bodio, C. Willis, C. Billaud, T. Le Gall, C. Mioskowski, Tetrahedron, 2008, 64, 8930.CrossRefGoogle Scholar
  9. 9.
    N. G. Kozlov, S. L. Bondarev, A. P. Kadutskii, L. I. Basalaeva, F. S. Pashkovskii, Zh. Org. Khim., 2008, 44, 1041 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44, 1031].Google Scholar
  10. 10.
    A. Shaabany, E. Soleimani, A. Sarvary, A. H. Rezayan, Bioorg. Med. Chem. Lett., 2008, 3968.Google Scholar
  11. 11.
    A. Shaabany, A. Sarvary, S. Keshipour, A. H. Rezayan, R. Ghadari, Tetrahedron, 2010, 66, 1911.CrossRefGoogle Scholar
  12. 12.
    F. Shi, N. Ma, Y. Zhany, G. Zhang, B. Jiang, S. Tu, Synth. Commun., 2010, 40, 235.CrossRefGoogle Scholar
  13. 13.
    V. A. Dorokhov, M. F. Gordeev, Z. K. Dem’yanets, M. N. Bochkareva, V. S. Bogdanov, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 1654 [Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 1806].CrossRefGoogle Scholar
  14. 14.
    V. A. Dorokhov, Z. K. Dem’yanets, Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 384 [Izv. Akad. Nauk, Ser. Khim., 1993, 419].CrossRefGoogle Scholar
  15. 15.
    V. A. Voronkova, A. V. Komkov, V. A. Dorokhov, Russ. Chem. Bull. (Int. Ed.), 2009, 58, 351 [Izv. Akad. Nauk, Ser. Khim., 2009, 347].CrossRefGoogle Scholar
  16. 16.
    V. L. Gein, S. G. Pitirimova, O. V. Vinokurova, Yu. S. Andreichikov, A. V. Komkov, V. S. Bogdanov, V. A. Dorokhov, Russ. Chem. Bull. (Engl. Transl.), 1994, 43, 1398 [Izv. Akad. Nauk, Ser. Khim., 1994, 1475].CrossRefGoogle Scholar
  17. 17.
    V. A. Dorokhov, M. A. Prezent, V. S. Bogdanov, Russ. Chem. Bull. (Engl. Transl.), 1994, 43, 1550 [Izv. Akad. Nauk, Ser. Khim., 1994, 1638].CrossRefGoogle Scholar
  18. 18.
    V. A. Dorokhov, V. A. Voronkova, A. V. Komkov, S. V. Baranin, L. S. Vasil’ev, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 1035 [Izv. Akad. Nauk, Ser. Khim., 2010, 1012].CrossRefGoogle Scholar
  19. 19.
    J. Sandstrom, Topics in Stereochemistry, Eds H. L. Alinger, E. L. Elial, S. H. Wilen, John Wiley, New York, 1983, 14, p. 83.CrossRefGoogle Scholar
  20. 20.
    V. S. Plugin, S. L. Kuznetsova, Yu. E. Sapozhnikov, Zh. Org. Khim., 2008, 44, 461 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44].Google Scholar

Copyright information

© Springer Science+Business Media New York 2012

Authors and Affiliations

  1. 1.N. D. Zelinsky Institute of Organic ChemistryRussian Academy of SciencesMoscowRussian Federation

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