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Synthesis of 10-(R-benzoyl)-2,4-dimethyl-6-(R-phenyl)-8,9-dihydropyrimido[5,4-e]pyrrolo[1,2-c]pyrimidine-1,3(2H,4H)-diones and 2,4-dimethyl-9,10-dihydro-6λ4-pyrimido[5,4-d]pyrrolo- [1,2-b][1,2,6]thiadiazine-1,3,6(2H,4H,8H)-trione

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Abstract

6-Imino-1,3-dimethyl-5-(pyrrolidin-2-ylidene)-5,6-dihydropyrimidine-2,4(1H,3H)-dione reacted with substituted benzoyl chlorides in the presence of triethylamine to give the corresponding 10-(R-benzoyl)-2,4-dimethyl-6-(R-phenyl)-8,9-dihydropyrimido[5,4-e]pyrrolo[1,2-c]pyrimidine-1,3(2H,4H)-diones. Analogous reaction with thionyl chloride afforded 2,4-dimethyl-9,10-dihydro-6λ4-pyrimido[5,4-d]pyrrolo[1,2-b][1,2,6]-thiadiazine-1,3,6(2H,4H,8H)-trione.

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References

  1. Sanghhvi, Y.S., Larson, S.B., Matsumoto, S.S., Nord, L.D., Smee, D.F., Willis, R.C., Avery, T.L., Robins, R.K., and Revankar, G.R., J. Med. Chem., 1989, vol. 32, no. 3, p. 629.

    Article  Google Scholar 

  2. Tenser, R.B., Gaydos, A., and Hay K.A., Antimicrob. Agents Chemother., 2001, vol. 45, no. 12, p. 3657.

    Article  CAS  Google Scholar 

  3. De la Cruz, J.P., Carrasco, T., Ortega, G., and Sanchez De la Cuesta, F., Lipids, 1992, vol. 27, no. 3, p. 192.

    Article  Google Scholar 

  4. Furuya, S. and Ohtaki, T., EP Patent no. 608565, 1994; Chem. Abstr., 1994, vol. 121, no. 205 395 w.

    Google Scholar 

  5. Singh, G., Singh, G., Yadav, A.K., and Mishraa, K., Indian J. Chem., Sect. B, 2002, vol. 41, no. 2, p. 430.

    Google Scholar 

  6. Bernier, J.L., Henichart, J.P., Warin, V., and Baert, F., J. Pharm. Sci., 1980, vol. 69, no. 11, p. 1343.

    Article  CAS  Google Scholar 

  7. Hamama, W.S., Ismail, M.A., Al-Saman, H.A., and Zoorob, H.H., J. Adv. Res., 2013, vol. 4, p. 115.

    Article  CAS  Google Scholar 

  8. Martirosyan, A., Tamazyan, R., Gasparyan, S., Alexanyan, M., Panosyan, H., Martirosyan, V., and Schinazi, R., Tetrahedron Lett., 2010, vol. 51, p. 231.

    Article  CAS  Google Scholar 

  9. Eksperimental’naya otsenka protivoopukholevykh preparatov v SSSR i SShA (Experimental Assessment of Antitumor Drugs in the USSR and USA), Sof’ina, Z.P., et al., Eds., Moscow: Meditsina, 1980.

  10. North, A.C.T., Phillips, D.C., and Mathews, F.S., Acta Crystallogr., Sect. A, 1968, vol. 24, p. 351.

    Article  Google Scholar 

  11. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3.

    Article  Google Scholar 

Download references

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Authors and Affiliations

  1. Mndzhoyan Institute of Fine Organic Chemistry Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    S. P. Gasparyan, M. V. Alexanyan, G. K. Harutyunyan, A. H. Martirosyan, H. M. Stepanyan & R. E. Muradyan

  2. Molecular Structure Research Center, National Academy of Sciences of Armenia, pr. Azatutyan 26, Yerevan, 0014, Armenia

    R. A. Tamazyan & A. G. Ayvazyan

Authors
  1. S. P. Gasparyan
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  2. M. V. Alexanyan
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  3. G. K. Harutyunyan
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  4. A. H. Martirosyan
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  5. H. M. Stepanyan
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  6. R. E. Muradyan
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  7. R. A. Tamazyan
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  8. A. G. Ayvazyan
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Corresponding author

Correspondence to S. P. Gasparyan.

Additional information

Original Russian Text © S.P. Gasparyan, M.V. Alexanyan, G.K. Harutyunyan, A.H. Martirosyan, H.M. Stepanyan, R.E. Muradyan, R.A. Tamazyan, A.G. Ayvazyan, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1359–1363.

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Gasparyan, S.P., Alexanyan, M.V., Harutyunyan, G.K. et al. Synthesis of 10-(R-benzoyl)-2,4-dimethyl-6-(R-phenyl)-8,9-dihydropyrimido[5,4-e]pyrrolo[1,2-c]pyrimidine-1,3(2H,4H)-diones and 2,4-dimethyl-9,10-dihydro-6λ4-pyrimido[5,4-d]pyrrolo- [1,2-b][1,2,6]thiadiazine-1,3,6(2H,4H,8H)-trione. Russ J Org Chem 52, 1348–1352 (2016). https://doi.org/10.1134/S1070428016090177

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  • DOI: https://doi.org/10.1134/S1070428016090177

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