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Efficient synthesis of novel heterocyclic dihydropyrimidine-2,4,5(3H)-trione and tetrahydro-2-thioxopyrimidine-4,5-dione derivatives

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Abstract

Novel heterocyclic dihydropyrimidine-2,4,5(3H)-triones and tetrahydro-2-thioxopyrimidine-4,5-diones were synthesized via three-component reaction between appropriate amines, phenyl isocyanate or phenyl isothiocyanate, and ethyl bromopyruvate in DMF under reflux conditions without using additional bases or catalysts. All the products were obtained in good yield by simple and efficient procedure. The structures of all the synthesized compounds were established from advanced spectroscopic data.

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References

  1. C.O. Kappe, Tetrahedron 49, 6937 (1993)

    Article  CAS  Google Scholar 

  2. H. Cho, M. Ueda, K. Shima et al., J. Med. Chem. 32, 2399 (1989)

    Article  CAS  Google Scholar 

  3. K.S. Atwal, B.N. Swanson, S.E. Unger et al., J. Med. Chem. 34, 806 (1991)

    Article  CAS  Google Scholar 

  4. B. Schnell, U.T. Strauss, P. Verdino, K. Faber, C.O. Kappe, Tetrahedron Asymmetry 11, 1449 (2000)

    Article  CAS  Google Scholar 

  5. B.B. Snider, Z. Shi, J. Org. Chem. 58, 3828 (1993)

    Article  CAS  Google Scholar 

  6. J.H. Clark (VCH Publishers, New York, 1994)

  7. R.A. Sheldon, H. VanBekkum (Wiely-VCH, Weinheim, 2002)

  8. G.D. Yadav, M.S. Krishnan, Org. Process Res. Dev. 2, 86 (1998)

    Article  CAS  Google Scholar 

  9. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893)

    Google Scholar 

  10. N.R. Penthala, T.R. Yerramreddy, N.R. Madadi, V. Sonar, P.A. Crooks, in Breast Cancer - Current and Alternative Therapeutic Modalities, (InTech, Shanghai, 2011), p. 283

  11. N.R. Madadi, Y.R. Reddy, N.R. Reddy, S. Parkin, P.A. Crooks, Acta Crystallogr. Sect. E E66, o1792 (2010)

    Article  Google Scholar 

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Acknowledgments

We are thankful to the Office of Graduate Studies of the Vali-e-Asr University of Rafsanjan for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, Vali-e-Asr University of Rafsanjan, 77176, Rafsanjan, Iran

    Hossein Mehrabi & Farzaneh Alizadeh-bami

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  1. Hossein Mehrabi
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  2. Farzaneh Alizadeh-bami
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Correspondence to Hossein Mehrabi.

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Mehrabi, H., Alizadeh-bami, F. Efficient synthesis of novel heterocyclic dihydropyrimidine-2,4,5(3H)-trione and tetrahydro-2-thioxopyrimidine-4,5-dione derivatives. J IRAN CHEM SOC 12, 1275–1279 (2015). https://doi.org/10.1007/s13738-015-0591-2

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  • DOI: https://doi.org/10.1007/s13738-015-0591-2

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