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Sodium hydrogen sulfate as a catalyst for the synthesis of N,4-diaryl-6-methyl-1-methyl(phenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides via the Biginelli reaction

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Chemistry of Heterocyclic Compounds Aims and scope

N,4-Diaryl-6-methyl-1-methyl(phenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides were synthesized in three-component reaction of N-aryl-3-oxobutanamides, aromatic aldehyde, and N-methylthiourea (N-phenylthiourea) in ethanol in the presence of nontoxic, cheap sodium hydrogen sulfate as a catalyst. Products were obtained in moderate to high yields.

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References

  1. (a) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Callejo, R.; Ruiz, M. P.; Torres, M. R. Eur. J. Org. Chem. 2012, 12, 2359. (b) Terrett, N. K.; Gardner, M.; Gordon, D. W.; Kobylecki, R. J.; Steele, J. Tetrahedron 1995, 51, 8135. (c) Yavari, I.; Beheshti, S. J. Iran. Chem. Soc. 2011, 8, 1030. (d) Domling, A. Chem. Rev. 2006, 106, 17. (e) Liu, J.; Lei, M.; Hu, L. Green Chem. 2012, 14, 840. (f) Ugi, I. Int. J. Pure Appl. Chem. 2001, 73, 187. (g) Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306. (h) Gein, V. L.; Yankin, A. N.; Nosova, N. V.; Dmitriev, M. V.; Slepukhin, P. A. Tetrahedron Lett. 2016, 57, 2441.

  2. (a) Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360. (b) Kappe, C. O. Tetrahedron 1993, 49, 6937. (c) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043. (d) Wan, J.-P.; Liu, Y. Synthesis 2010, 3943. (e) Nagarajaiah, H.; Mukhopadhyay, A.; Moorthy, J. N. Tetrahedron Lett. 2016, 57, 5135.

  3. Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806.

    Article  CAS  Google Scholar 

  4. (a) Haggarty, S. J.; Mayer, T. U.; Miyamoto, D. T.; Fathi, R.; King, R. W.; Mitchison, T. J.; Schreiber, S. L. Chem. Biol. 2000, 7, 275. (b) Fewell, S. W.; Smith, C. M.; Lyon, M. A.; Dumitrescu, T. P.; Wipf, P.; Day, B. W.; Brodsky, J. L. J. Biol.Chem. 2004, 279, 51131. (c) Karkola, S.; Lilienkampf, A.; Wahala, K. ChemMedChem 2008, 3, 461.

  5. Lee, E. S.; Park, J.-G.; Jahng, Y. Tetrahedron Lett. 2003, 44, 1883.

    Article  CAS  Google Scholar 

  6. Zamanova, A. V.; Kurbanova, M. M.; Rzaeva, I. A.; Farzaliev, V. M.; Allakhverdiev M. A. Russ. J. Appl. Chem. 2010, 83, 293. [Zh. Prikl. Khim. 2010, 83, 293.]

  7. Ashok, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2007, 42, 380.

    Article  CAS  Google Scholar 

  8. (a) Mayer, T. M.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971. (b) Garcia-Saez, I.; DeBonis, S.; Lopez, R.; Trucco, F.; Rousseau, B.; Thuery, P.; Kozielski, F. J. Biol. Chem. 2007, 282, 9740. (c) Canto, R. F. S.; Bernardi, A.; Battastini, V. L. M. O.; Russowsky, D.; Eifler-Lima J. Braz. Chem. Soc. 2011, 22, 1379. (d) Rovnyak, G. C.; Atwal, K. S.; Hedberg, A.; Kimball, S. D.; Moreland, S.; Gougoutas, J. Z.; O'Reilly, B. C.; Schwartz, J.; Malley, M. F. J. Med. Chem. 1992, 35, 3254.

  9. Marvaniya, H. M.; Parikh, P. K.; Sen, D. J. J. Appl. Pharm. Sci. 2011, 1, 109.

    Google Scholar 

  10. Zalavadiya, P. D.; Ghetiya, R. M.; Dodiya, B. L.; Vekariya, P. B.; Joshi, H. S. J. Heterocycl. Chem. 2013, 50, 973.

    Article  CAS  Google Scholar 

  11. Gein, V. L.; Zamaraeva, Т. М.; Dmitriev, М. V. Russ. J. Gen. Chem. 2017, 87, 350. [Zh. Obshch. Khim. 2017, 87, 336.]

  12. Chitra, S.; Pandiarajan, K. Tetrahedron Lett. 2009, 50, 2222.

    Article  CAS  Google Scholar 

  13. Rodriguez-Dominguez, J. C.; Bernardi, D.; Kirsch, G. Tetrahedron Lett. 2007, 48, 5777.

    Article  CAS  Google Scholar 

  14. Nandurkar, N. S.; Bhanushali, M. J.; Bhor, M. D.; Bhanage, B. M. J. Mol. Catal. A: Chem. 2007, 271, 14.

    Article  CAS  Google Scholar 

  15. Gohain, M.; Prajapati, D.; Sandhu, J. S. Synlett 2004, 235.

  16. Lu, J.; Ma, H. Synlett 2000, 63.

  17. Varala, R.; Alam, M. M.; Adapa, S. R. Synlett 2003, 67.

  18. Pandey, J.; Anand, N.; Tripathi, R. P. Tetrahedron 2009, 65, 9350.

    Article  CAS  Google Scholar 

  19. Starcevich, J. T.; Laughlin, T. J.; Mohan, R. S. Tetrahedron Lett. 2013, 54, 983.

    Article  CAS  Google Scholar 

  20. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270.

    Article  CAS  Google Scholar 

  21. Munoz-Muniz, O.; Juaristi, E. ARKIVOC 2003, (xi), 16.

  22. Sadek, K. U.; Al-Qalaf, F.; Abdelkhalik, M. M.; Elnagdi, M. H. J. Heterocycl. Chem. 2010, 47, 284.

    CAS  Google Scholar 

  23. Kolosov, M. A.; Kulyk, O. G.; Al-Ogaili, M. J. K.; Orlov, V. D. Tetrahedron Lett. 2015, 56, 4666.

    Article  CAS  Google Scholar 

  24. Zamaraeva, T. M.; Odegova, T. F.; Fedotov, A. Yu.; Tomilov, M. V.; Gein, V. L.; Slepukhin, P. A. Russ. J. Gen. Chem. 2014, 84, 1950. [Zh. Obshch. Khim. 2014, 84, 1672.]

  25. Cheng, Q.; Wang, Q.; Xu, X.; Ruan, M.; Yao, H.; Yang, X. J. Heterocycl. Chem. 2010, 47, 624.

    Article  CAS  Google Scholar 

  26. Cheng, Q.; Wang, Q.; Tan, T.; Chen, N.; Shuai, M. J. Heterocycl. Chem. 2012, 49, 1352.

    Article  CAS  Google Scholar 

  27. Zamaraeva, T. M.; Gein, V. L.; Buzmakova, N. A., Dmitriev, M. V. Russ. J. Org. Chem. 2016, 52, 1022. [Zh. Org. Khim. 2016, 52, 1028.]

  28. Gein, V. L.; Zamaraeva, T. M.; Dmitriev, M. V.; Nasakin, O. E. Russ. J. Org. Chem. 2017, 53, 869. [Zh. Org. Khim. 2017, 53, 853.]

  29. Gein, V. L.; Zamaraeva, T. M.; Buzmakova, N. A.; Dmitriev, M. V.; Nasakin, O. E.; Kazantseva, M. I. Russ. Org. Chem. 2017, 53, 86. [Zh. Org. Khim. 2017, 53, 90.]

  30. Raj, M. K.; Rao, H. S. P.; Manjunatha, S. G.; Sridharan, R.; Nambiar, S.; Keshwan, J.; Rappai, J.; Bhagat, S.; Shwetha, B. S.; Hegde, D.; Santhosh, U. Tetrahedron Lett. 2011, 52, 3605.

    Article  Google Scholar 

  31. Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R.; van de Streek, J.; Wood, P. A. J. Appl. Crystallogr. 2008, 41, 466.

    Article  CAS  Google Scholar 

  32. CrysAlisPro, Version 1.171.37.33; Agilent Technologies, 2014.

  33. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

  34. Palatinus L.; Chapuis G. J. Appl. Crystallogr. 2007, 40, 786.

    Article  CAS  Google Scholar 

  35. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

    Google Scholar 

  36. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, 2 Polevaya St., Perm, 614081, Russia

    Vladimir L. Gein & Tatiana M. Zamaraeva

  2. Perm State University, 15 Bukireva St., Perm, 614068, Russia

    Maksim V. Dmitriev

Authors
  1. Vladimir L. Gein
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  2. Tatiana M. Zamaraeva
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  3. Maksim V. Dmitriev
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Correspondence to Vladimir L. Gein.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(2), 177–182

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Gein, V.L., Zamaraeva, T.M. & Dmitriev, M.V. Sodium hydrogen sulfate as a catalyst for the synthesis of N,4-diaryl-6-methyl-1-methyl(phenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides via the Biginelli reaction. Chem Heterocycl Comp 54, 177–182 (2018). https://doi.org/10.1007/s10593-018-2251-9

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