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Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of 1,3-dihydro-2Н-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2Н-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.

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References

  1. K.-L. Yu, Y. Zhang, R. L. Civiello, A. K. Trehan, B. C. Pearce, Z. Yin, K. D. Combrink, H. B. Gulgeze, X. A. Wang, K. F. Kadow, C. W. Cianci, M. Krystal, and N. A. Meanwell, Bioorg. Med. Chem. Lett., 14, 1133 (2004).

    Article  CAS  Google Scholar 

  2. D. L. Evers, G. Komazin, D. Shin, D. D. Hwang, L. B. Townsend, and J. C. Drach, Antiviral Res., 56, 61 (2002).

    Article  CAS  Google Scholar 

  3. A. D. Jordan, A. H. Vaidya, D. I. Rosenthal, B. Dubinsky, C. P. Kordik, P. J. Sanfilippo, W. N. Wu, and A. B. Reitz, Bioorg. Med. Chem. Lett., 12, 2381 (2002).

    Article  CAS  Google Scholar 

  4. A. Orjales, R. Mosquera, L. Labeaga, and R. Rodes, J. Med. Chem., 40, 586 (1997). A. P. Thomas, C. P. Allot, K. H. Gibson, J. S. Major, B. B. Masek, A. A. Oldham, A. H. Ratchiffe, D. A. Russell, and D. A. Thomason, J. Med. Chem., 35, 877 (1992).

  5. F. R. Basford, F. H. S. Curd, and F. L. Rose, GB Pat. Appl. 593499.

  6. J. L. H. van Gelder, A. H. M. Raeymaekers, and L. F. C. Roevens, DE Pat. Appl. 2029637.

  7. K. M. Hosamani and R. V. Shingalapur, Arch. Pharm., 344, 311 (2011).

    Article  CAS  Google Scholar 

  8. V. A. Mauro, H. C. Silvia, V. A. Joao, and V. N. S. Marcus, J. Sulfur Chem., 28, 17 (2007).

    Article  Google Scholar 

  9. M. Andrzejewska, L. Yepez-Mulia, A. Tapia, R. Cedillo-Rivera, A. E. Laudy, B. J. Starosciak, and Z. Kazimierczuk, Eur. J. Pharm. Sci., 21, 323 (2004).

    Article  CAS  Google Scholar 

  10. R. Dahiya and R. Kaur, Biosci., Biotechnol. Res. Asia, 4, 561 (2007).

  11. M. Marco, B. F. S. Claudia, S. Rivara, Z. Valentina, V. Federica, R. Mirko, B. Elisabetta, B. Simona, B. Vigilio, M. Francesca, and I. Mariannina, V. P. Pier, Bioorg. Med. Chem., 12, 663 (2004).

    Article  Google Scholar 

  12. M. S. Reddy, R. N. Anisetti, K. D. Prasad, S. Sannigrahi, and P. A. Reddy, Pharm. Chem. J., 44, 642 (2011).

    Article  CAS  Google Scholar 

  13. E. V. Bakhareva, M. G. Voronkov, M. S. Sorokin, V. A. Lopyrev, S. B. Seredenin, and G. M. Gaidarov, Pharm. Chem. J., 30, 89 (1996). [Khim.-Farm. Zh., No. 2, 20 (1996).]

  14. K. Anandrajagopal, R. N. Tiwari, K. G. Bothara, J. A. J. Sunilson, C. Dineshkumar, and P. Promwichit, Adv. Appl. Sci. Res., 1, 132 (2010).

    Google Scholar 

  15. G. Sach, Scand. J. Gastroenterol. Suppl., 21, 1 (1986).

    Article  Google Scholar 

  16. D. Carcanague, Y. K. Shue, M. A. Wuonola, M. U. Nickelsen, C. Joubran, J. K. Abedi, J. Jones, and T. C. Kuhler, J. Med. Chem., 45, 4300 (2002).

    Article  CAS  Google Scholar 

  17. E. V. Ryaskina, M. V. Voronin, and S. B. Seredenin, Pharm. Chem. J., 46, 334 (2012). [Khim.-Farm. Zh., No. 6, 12 (2012).]

  18. Ya. M. Vakhrushev and N. A. Khokhlacheva, Eksperim. i Klin. Gastroenterol., No. 4, 105 (2010).

  19. I. Szanyi, L. Lujber, I. Gerlinger, J. Pytel, M. Bauer, A. Csejtey, E. Szele, K. Gombos, I. Kiss, S. Seredenin, M. Yarkova, and I. Ember, In Vivo, 21, 1059 (2007).

    CAS  Google Scholar 

  20. G. Absalan and A. Aghaei Goudi, J. Korean Chem. Soc., 51, 141 (2007).

    Article  CAS  Google Scholar 

  21. H. Bagheri and A. Gholami, Talanta, 55, 1141 (2001).

    Article  CAS  Google Scholar 

  22. D. M. Manohar, K. Anoop Krishnan, and T. S. Anirudhan, Water Res., 36, 1609 (2002).

    Article  CAS  Google Scholar 

  23. N. Pourreza and K. Ghanemi, J. Hazard. Mater., 161, 982 (2009).

    Article  CAS  Google Scholar 

  24. F. Zavarise, D. Merli, and A. Profumo, Anal. Chim. Acta, 668, 177 (2010).

    Article  CAS  Google Scholar 

  25. O. L. Humenyuk, O. I. Syza, and O. M. Krasovs'kyi, Mater. Sci., 43, 91 (2007).

    Article  CAS  Google Scholar 

  26. M. Finšgar, Corros. Sci., 72, 90 (2013).

    Article  Google Scholar 

  27. L. Wang, J.-X. Pu, and H.-C. Luo, Corros. Sci., 45, 677 (2003).

    Article  CAS  Google Scholar 

  28. M. Mahdavian and S. Ashhari, Electrochim. Acta, 55, 1720 (2010).

    Article  CAS  Google Scholar 

  29. H. Zinner, O. Schmitt, W. Schritt, and G. Rembarz, Chem. Ber., 90, 2852 (1957).

    Article  CAS  Google Scholar 

  30. A. M. Gazaliev, M. K. Ibraev, M. B. Isabaeva, and Zh. A. Ibataev, Russ. J. Gen. Chem., 83, 1098 (2013). [Zh. Obsch. Khim., 83, 967 (2013).]

  31. W. S. Hamama, J. Chem. Res., Synop., 269 (2000).

  32. B. Stanovnik and M. Tišler, Arch. Pharm., 298, 357 (1965).

    Article  CAS  Google Scholar 

  33. R. S. Varma and D Chatterjee, J. Ind. Chem. Soc., 60, 1077 (1983).

    CAS  Google Scholar 

  34. R. S. Varma, S. Chauhan, and C. R. Prasad, Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 22B, 705 (1983).

    CAS  Google Scholar 

  35. R. S. Varma, S. Chauhan, and C. R. Prasad, Ind. J. Chem., Sect. B: Org. Chem. Incl. Med. Chem., 27B, 438 (1988).

    CAS  Google Scholar 

  36. A. A. Hassan, Phosphorus, Sulfur Silicon Relat. Elem., 106, 55 (1995).

    Article  CAS  Google Scholar 

  37. http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi.

  38. V. Yu. Vvedenskii and E. D. Shtefan, Russ. Chem. Rev., 65, 307 (1996). [Usp. Khim., 65, 326 (1996).]

  39. Y.-M. Guo and B.-Z. Li, Acta Chim. Sinica, 65, 1561 (2007).

    CAS  Google Scholar 

  40. S. Vijayaraghavan, R. R. Somani, P. Y. Shirodkar, and V. J. Kadam, Int. J. PharmTech. Res., 1, 811 (2009).

    CAS  Google Scholar 

  41. H. P. Narkhede, U. B. More, D.S. Dalal, and P. P. Mahulikar, J. Sci. Ind. Res., 67, 374 (2008).

    CAS  Google Scholar 

  42. S. Ram, D. S. Wise, and L. B. Townsend, J. Heterocycl. Chem., 22, 1269 (1985).

    Article  CAS  Google Scholar 

  43. S. A. Nevade, S. G. Lokapure, and N. V. Kalyane, J. Korean Chem. Soc., 57, 755 (2013).

    Article  CAS  Google Scholar 

  44. A. L. Misra, J. Org. Chem., 23, 897 (1958).

    Article  CAS  Google Scholar 

  45. K. B. Wiberg and Y. Wang, ARKIVOC, v, 45 (2011).

  46. M. R. Truter, Acta Crystallogr., 22, 556 (1967).

    Article  CAS  Google Scholar 

  47. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found Crystallogr., A64, 112 (2008).

  48. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann, J. Appl. Crystallogr., 42, 339 (2009).

    Article  CAS  Google Scholar 

  49. CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012).

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This work received financial support from the Russian Science Foundation (grant No. 14-13-00126). The experiments were performed by using equipment at the Saint Petersburg State University Resource Centers "Center for Magnetic Resonance Research", "Center for X-ray Diffraction Studies", "Center for Chemical Analysis and Material Research".

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Correspondence to M. A. Kuznetsov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1684–1696, November, 2014.

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Bespalov, A.Y., Gorchakova, T.L., Ivanov, A.Y. et al. Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione. Chem Heterocycl Comp 50, 1547–1558 (2015). https://doi.org/10.1007/s10593-014-1623-z

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