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Secondary 3-Aminothieno[2,3-b]Pyridine-2-Carboxamides in Reaction with ortho-Formylbenzoic Acid

Chemistry of Heterocyclic Compounds volume 50, pages 1756–1767 (2015)Cite this article

The reaction of secondary 3-aminothieno[2,3-b]pyridine-2-carboxamides with ortho-formylbenzoic acid gave angular (±)-7,7a-dihydropyrido[3",2":4',5']thieno[2',3':5,6]pyrimido[2,1-a]isoindole-6,12-diones. The intermediate products, (±)-(1,2,3,4-tetrahydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl)benzoic acids, were isolated in some cases. Secondary N-[(5-methylfuran-2-yl)methyl]carboxamides were shown to form linear isoindole-6,8-diones in this reaction. One of the angular isoindole-6,12-dione derivatives was studied by X-ray structural analysis. Dynamic NMR was used to characterize the degenerate intramolecular rotation in molecules of isoindole-6,12-diones.

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References

  1. V. K. Vasilin, D. Yu. Lukina, T. A. Stroganova, and G. D. Krapivin, Chem. Heterocycl. Compd., 50, 1486 (2014). [Khim. Geterotsikl. Soedin., 1614 (2014).]

  2. S. K. Meegalla, G. J. Stevens, C. A. McQueen, A. Y. Chen, C. Yu, L. F. Liu, L. R. Barrows, and E. J. LaVoie, J. Med. Chem., 37, 3434 (1994).

    Article  CAS  Google Scholar 

  3. S. N. Khattab, S. Y. Hassan, A. El-Faham, A. M. M. El Massry, and A. Amer, J. Heterocycl. Chem., 44, 617 (2007).

    Article  CAS  Google Scholar 

  4. V. V. Lyaskovskyy, Z. V. Voitenko, and V. A. Kovtunenko, Chem. Heterocycl. Compd., 43, 253 (2007). [Khim. Geterotsikl. Soedin., 323 (2007).]

  5. K. S. Kumar, P. M. Kumar, K. A. Kumar, M. Sreenivasulu, A. A. Jafar, D. Rambabu, G. R. Krishna, C. M. Reddy, R. Kapavarapu, K. Shivakumar, K. Krishna Priya, K. V. L. Parsa, and M. Pal, Chem. Commun., 5010 (2011).

  6. V. K. Vasilin, D. Yu. Lukina, T. A. Stroganova, and G. D. Krapivin, Chem. Heterocycl. Compd., 49, 1530 (2014). [Khim. Geterotsikl. Soedin., 1650 (2013).]

  7. T. A. Stroganova, V. K. Vasilin, E. A. Zelenskaya, V. M. Red'kin, and G. D. Krapivin, Synthesis, 19, 3088 (2008).

    Article  Google Scholar 

  8. M. Nogradi, Stereochemistry: Basic Concepts and Applications [Russian translation], Mir, Moscow (1984), p. 175.

    Google Scholar 

  9. E. A. Kaigorodova, A. A. Osipova, M. M. Lipunov, and G. D. Krapivin, Izv. Vuzov. Khim. i Khim. Tekhnol., 47, 107 (2004).

    CAS  Google Scholar 

  10. G. M. Sheldrick, SHELXL-97: Program for the Solution of Crystal Structures. University of Göttingen (1997).

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Authors and Affiliations

  1. Kuban State Technological University, 2 Moskovskaya St., Krasnodar, 350072, Russia

    V. K. Vasilin, D. Yu. Lukina, T. A. Stroganova & G. D. Krapivin

  2. Southern Federal University, 7 Zorge St., Rostov-on-Don, 344090, Russia

    P. G. Morozov

Authors
  1. V. K. Vasilin
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  2. D. Yu. Lukina
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  3. T. A. Stroganova
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  4. P. G. Morozov
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  5. G. D. Krapivin
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Correspondence to G. D. Krapivin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1908–1919, December, 2014.

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Vasilin, V.K., Lukina, D.Y., Stroganova, T.A. et al. Secondary 3-Aminothieno[2,3-b]Pyridine-2-Carboxamides in Reaction with ortho-Formylbenzoic Acid. Chem Heterocycl Comp 50, 1756–1767 (2015). https://doi.org/10.1007/s10593-015-1648-y

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  • DOI: https://doi.org/10.1007/s10593-015-1648-y

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