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Unusual reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-r-1,2-dihydropyridin-2-ones with nitrogen-containing 1,4-dinucleophiles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyridin-2-ones with the nitrogen-containing 1,4-dinucleophiles o-phenylenediamine, o-aminothiophenol, and ethylenediamine, proceeds as a recyclization, the products of which are derivatives of 5-(1H-benzimidazol-2-yl)-2H-2-pyranone, 5-(benzothiazol-2-yl)-2H-2-pyranone, and 5-(4,5-dihydro-1H-imidazol-2-yl)-2H-2-pyra-none respectively.

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References

  1. H. Schirok, C. Alonso-Alija, and M. Michels, Synthesis, 3085 (2005).

  2. S. Chacrabarti, K. Panda, N. C. Misra, H. Illa, and H. Junjappa, Synlett., 1437 (2005).

  3. R. T. Chakrasali, H. Illa, and H. Junjappa, Synthesis, 87 (1988).

  4. J. Becher, H. Nissen, and K. S. Varma, Liebigs Ann. Chem., 6, 1109 (1986).

    Article  Google Scholar 

  5. P. Neelakantan, M. F. Rahman, and U. T. Bhalerao, Indian J. Chem., 26B, 1086 (1987).

    CAS  Google Scholar 

  6. V. N. Britsun, A. N. Esipenko, A. N. Chernega, E. B. Rusanov, and M. O. Lozinskii, Khim. Geterotsikl. Soedin., 1660 (2007). [Chem. Heterocycl. Comp., 43, 1411 (2007)].

    Google Scholar 

  7. A. F. Pozharskii, Theoretical Basis of Heterocyclic Chemistry [in Russian], Khimiya, Moscow (1985), p. 118.

    Google Scholar 

  8. R. Mukherjee and A. Chatterjee, Tetrahedron, 22, 1461 (1966).

    Article  CAS  Google Scholar 

  9. T. Eicher, E. Angerer, and A. M. Hansen, Liebigs Ann. Chem., 746, 102 (1971).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 02660, Ukraine

    V. N. Britsun, A. N. Esipenko & M. O. Lozinskii

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  1. V. N. Britsun
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  2. A. N. Esipenko
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  3. M. O. Lozinskii
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Correspondence to V. N. Britsun.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1089–1095, July, 2008.

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Britsun, V.N., Esipenko, A.N. & Lozinskii, M.O. Unusual reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-r-1,2-dihydropyridin-2-ones with nitrogen-containing 1,4-dinucleophiles. Chem Heterocycl Comp 44, 876–881 (2008). https://doi.org/10.1007/s10593-008-0124-3

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  • DOI: https://doi.org/10.1007/s10593-008-0124-3

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