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Cyclothiomethylation of primary amines with formaldehyde and hydrogen sulfide to nitrogen- and sulfur-containing heterocycles (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Published data and the authors' own experimental results on the synthesis of nitrogen- and sulfur-containing heterocycles based on the cyclothiomethylation of amines with formaldehyde and H2S are reviewed. Features of the three-component condensation are discussed in relation to the nature and structure of the initial amines and also the reaction conditions.

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References

  1. M. D. Mashkovskii, Drugs [in Russian], Meditsina, Moscow (1986), Vol. 2, p. 280.

    Google Scholar 

  2. R. G. Glushkova, G. A. Modnikova, A. I. L'vov, L. Yu. Krylova, T. V. Pushkina, T. A. Gus'kova, and N. P. Solov'eva, Khim.-Farm. Zhurn., 38, No. 8, 16 (2004).

    Google Scholar 

  3. S. N. Pandeya and P. Ram, Indian J. Chem., 20B, 825 (1981).

    CAS  Google Scholar 

  4. L. G. Toldi, Khim. Geterotsikl. Soedin., 878 (1978). [Chem. Heterocycl. Comp., 14, 705 (1978)].

    Google Scholar 

  5. V. I. Ivanskii, Chemistry of Heterocyclic Compounds [in Russian], Vysshaya Shkola, Moscow (1978).

    Google Scholar 

  6. M. A. Yurovskaya, Chemistry of Heterocyclic Compounds [in Russian], Mir, Moscow (1996).

    Google Scholar 

  7. D. Barton, W. D. Ollis (editors), Comprehensive Organic Chemistry [Russian translation] (1985), Vol. 9.

  8. B. A. Trofimov and N. K. Gusarova, Uspekhi Khimii, 76, 550 (2007).

    Google Scholar 

  9. K. V. Kudryavtsev and A. A. Zagulyaeva, Zh. Org. Khim., 44, 384 (2008).

    Google Scholar 

  10. J. C. Gálvez-Ruiz, C. Guadarrama-Pérez, H. Nöth, and A. Flores-Parra, Eur. J. Inorg. Chem., 601 (2004).

  11. A. Flores-Parra, G. Cadenas-Pliego, L. M. Martinez-Agulera, M. L. Garcia-Nares, and R. Contreras, Chem. Ber., 126, 863 (1993).

    Article  CAS  Google Scholar 

  12. Deutsche Gold- und Silber-Scheideanstalt vorm. Roessler, French Pat., 1 341 792 (1963); Chem. Abstr., 5, 398 (1964).

  13. R. R. Gafiatullin, Dis. Cand. Chem. Sci. [in Russian], Ufa (2000).

  14. Brit. Pat. 943 273 (1963); Chem. Abstr., 60, 5528 (1964).

    Google Scholar 

  15. Nihon Nohyaku Co., Ltd., Jpn Pat. JP 6004177 (1985); Chem. Abstr., 102, 149292 (1985).

  16. H. W. Brinkman, H. Copier, J. J. M. de Leuw, and S. B. Tjan, J. Agr. Food Chem., 20, 177 (1972).

    Article  CAS  Google Scholar 

  17. G. MacLeod and B. M. Coppock, J. Agr. Food Chem., 25, 113 (1977).

    Article  CAS  Google Scholar 

  18. P. Farkas, P. Hradsky, and M. Kovac, Z. Lebensm.-Untersuch. Forsch., 195, 459 (1992).

    Article  CAS  Google Scholar 

  19. L. L. Hinrichsen and H. Andersen, J. Agr. Food Chem., 42, 1537 (1994).

    Article  CAS  Google Scholar 

  20. C. Shu, B. D. Mookherjee, and M. H. Vock, US Pat. 4235938, 1980; Ref. Zh. Khim., 23R282 (1981).

  21. C. Shu, B. D. Mookherjee, and M. H. Vock, US Pat. 4200741, 1980, Ref. Zh. Khim., 2R248 (1981).

  22. C. Shu, B. D. Mookherjee, and M. H. Vock, US Pat. 4228278, 1980; Ref. Zh. Khim., 11R270 (1981).

  23. A. Wohl, Berichte, 19, 2344 (1886).

    Google Scholar 

  24. T. E Glotova, A. S. Nakhmanovich, A. I. Albanov, N. I. Protsuk, T. V. Nizovtseva, and V. A. Lopyrev, 81 (2002). [Chem. Heterocycl. Comp., 38, 74 (2002)].

    Google Scholar 

  25. V. A. Trofimov, G. M. Gavrilov, G. A. Kalabin, V. V. Bairov, and S. V. Amosova, Khim. Geterotsikl. Soedin., 1466 (1979). [Chem. Heterocycl. Comp., 15, 1177 (1979)].

    Google Scholar 

  26. T. E. Glotova, N. I. Protsuk, M. Yu. Dvorko, and A. I. Albanov, Zh. Org. Khim., 40, 1269 (2004).

    Google Scholar 

  27. T. E. Glotova, N. I. Protsuk, and A. I. Albanov, Zh. Org. Khim., 39, 1749 (2003).

    Google Scholar 

  28. T. V. Kashik, G. V. Rassolova, G. M. Gavrilovа, V. I. Gostevskaya, S. V. Amosova, and B. A. Trofimov, Khim. Geterotsikl. Soedin., 333 (1983). [Chem. Heterocycl. Comp., 19, 268 (1983)].

    Google Scholar 

  29. V. K. Voronov, B. A. Trofimov, G. M. Gavrilovа, S. V. Amosova, and V. I. Gostevskaya, Khim. Geterotsikl. Soedin., 485 (1981). [Chem. Heterocycl. Comp., 17, 347 (1981)].

    Google Scholar 

  30. C. Giordano and A. Belli, Synthesis, 193 (1977).

  31. V. I. Gorbatenko and L. I. Samarai, Synthesis, 85 (1980).

  32. L. I. Samarai, V. I. Gorbatenko, and M. V. Vovk, Ukr. Khim. Zhurn., 55, 966 (1989).

    CAS  Google Scholar 

  33. M. V. Vovk, I. G. Krainikova, and V. I. Dorokhov, Khim. Geterotsikl. Soedin., 996 (1995). [Chem. Heterocycl. Comp., 31, 868 (1995)].

    Google Scholar 

  34. E. Schaumann, U. Wriede, and G. Adiwidjaja, Chem. Ber., 117, 2205 (1984).

    Article  CAS  Google Scholar 

  35. G. G. Butenko, A. N. Vereshchagin, and B. A. Arbuzov, Khim. Geterotsikl. Soedin., 321 (1972). [Chem. Heterocycl. Comp., 8, 290 (1972)].

    Google Scholar 

  36. R. D. Balanson, J. Org. Chem., 42, 393 (1977).

    Article  CAS  Google Scholar 

  37. G. Cadenas-Pliego, L. M. R. Martinez-Aguilera, A. M. Bello-Ramirez, M. J. Rosales-Hoz, R. Contreras, J. C. Daran, S. Halut, and A. Flores-Parra, Phosphorus, Sulfur, Silicon, 81, 111 (1993).

    Article  CAS  Google Scholar 

  38. A. Flores-Parra, S. A. Sanchez-Ruiz, C. Guadarrama, H. Noth, and R. Contreras, Eur. J. Inorg. Chem., 2069 (1999).

  39. C. Guadarrama-Pérez, G. Cadenas-Pliego, L. M. R. Martínez-Aguilera, and A. Flores-Parra, Chem. Ber., 130, 813 (1997).

    Article  Google Scholar 

  40. R. S. Aleev, Yu. S. Dal'nova, Yu. N. Popov, R. M. Masagutov, and S. R. Rafikov, Dokl. Akad. Nauk, 873 (1988).

  41. VEB Farbenfabric Wolfen, Ger. Pat. 1 155 450 (1963); Chem. Abstr., 60, 2941 (1964).

    Google Scholar 

  42. C. S. Le Fevre and R. I. W. Le Fevre, J. Chem. Soc., 1142 (1932).

  43. J. L. Nelson, C. Kenneth, and E. Y. Andrew, J. Org. Chem., 27, 2019 (1962).

    Article  Google Scholar 

  44. J. M. Lehn and F. G. Riddell, Chem. Comm., 21, 803 (1966).

    Google Scholar 

  45. E. R. Braithwaite and J. Graymore, J. Chem. Soc., 208 (1950).

  46. E. R. Braithwaite and J. Graymore, J. Chem. Soc., 143 (1953).

  47. D. Collins and J. Graymore, J. Chem. Soc., 4089 (1953).

  48. D. Collins and J. Graymore, J. Chem. Soc., 9 (1957).

  49. D. Collins and J. Graymore, J. Chem. Soc., 2893 (1958).

  50. G. Cadenas-Pliego, M. J. Rosales-Hoz, R. Contreras, and A. Flores-Parra, Tetrahedron: Asymmetry, 5, 633 (1994).

    Article  CAS  Google Scholar 

  51. L. Angiolini, R. P. Duke, R. A. Y. Jones, and A. R. Katritzky, J. Chem. Soc., Perkin Trans. 2, 674 (1972).

  52. S. R. Khafizova, V. R. Akhmetova, L. F. Korzhova, T. V. Khakimova, G. R. Nadyrgulova, R. V. Kunakova, E. A. Kruglov, and U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 423 (2005).

  53. A. Flores-Parra and S. A. Sánches-Ruíz, Heterocycles, 51, 2079 (1999).

    Article  CAS  Google Scholar 

  54. T. W. Campbell, J. Org. Chem., 22, 569 (1957).

    Article  CAS  Google Scholar 

  55. S. R. Khafizova, V. R. Akhmetova, R. V. Kunakova, and U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 1722 (2003).

  56. Y. Ogata, M. Okano, and M. Sugawara, J. Chem. Soc., 1715 (1954).

  57. T. Kawai, M. Irie, and M. Sakaguchi, J. Agr. Food Chem., 33, 393 (1985).

    Article  CAS  Google Scholar 

  58. Y. Zhang and H. Chi-Tang, J. Agr. Food Chem., 37, 1016 (1989).

    Article  CAS  Google Scholar 

  59. V. R. Akhmetova, G. R. Nadyrgulova, T. V. Tyumkina, Z. A. Starikova, M. Yu. Antipin, R. V. Kunakova, and U. M. Dzhemilev, Zh. Org. Khim., 43, 151 (2007).

    Google Scholar 

  60. J. F. Walker, Formaldehyde [Russian translation], Goskhimizdat, Moscow (1957).

    Google Scholar 

  61. A. N. Gafarov, L. N. Punegova, É. I. Loginova, S. S. Novikov, and N. K. Titov, Izv. Akad. Nauk, Ser. Khim., 2189 (1978).

  62. B. F. Kukharev, V. K. Stankevich, G. R. Klimenko, and A. N. Baranov, Zh. Prikl. Khim., 68, 142 (1995).

    CAS  Google Scholar 

  63. S. K. Ogorodnikov, Formaldehyde [in Russian], Khimiya, Leningrad (1984).

    Google Scholar 

  64. A. Y. Rulev, L. I. Larina, Y. A. Chuvashev, and V. V. Novorshonov, Mendeleev Commun., 128 (2005).

  65. J. C. Galvez-Ruiz, H. Noth, and A. Flores-Parra, Inorg. Chem., 42, 7596 (2003).

    Article  Google Scholar 

  66. J. C. Galvez-Ruiz, J. C. Jaen-Gaspar, I. G. Gastellanos-Arazola, R. Contreras, and A. Flores-Parra, Heterocycles, 10, 2269 (2004).

    Google Scholar 

  67. J. M. Bakke, J. Buhang, and J. Riha, Ind. Eng. Chem. Res., 40, 6051 (2001).

    Article  CAS  Google Scholar 

  68. U. M. Dzhemilev, R. S. Aleev, Yu. S. Dal'nova, R. V. Kunakova, S. R. Khafizova, S. V. Kovtunenko, A. A. Kalimunin, V. M. Andrianov, F. R. Ismagilov, and R. R. Gafiatullin, RF Pat. 2160233; Byul. Izobr., No. 34 (2000).

  69. F. E. Poppelsdorf and S. J. Holt, J. Chem. Soc., 1124 (1954).

  70. V. R. Akhmetova, G. R. Nadyrgulova, S. R. Khafizova, T. V. Tyumkina, A. A. Yakovenko, M. Yu. Antipin, L. M. Khalilov, R. V. Kunakova, U. M. Dzhemilev, Izv. Akad. Nauk, Ser. Khim., 305 (2006).

  71. G. R. Nadyrgulova, Dis. Cand. Chem. Sci. [in Russian], Ufa (2006).

  72. R. V. Kunakova, S. R. Khafizova, Yu. S. Dal'nova, R. S. Alev, L. M. Khalilov, and U. M. Dzhemilev, Neftekhimiya, 382 (2002).

  73. S. R. Khafizova, V. R. Akhmetova, G. R. Nadyrgulova, I. V. Rusakov, R. V. Kunakova, U. M. Dzhemilev, Neftekhimiya, 374 (2005).

  74. G. V. Gurskaya, Structures of Amino Acids [in Russian], Nauka, Moscow (1996), p. 158.

    Google Scholar 

  75. U. M. Dzhemilev, R. S. Aleev, Yu. S. Dal'nova, R. V. Kunakova, and S. R. Khafizova, RF Pat. 2206726; Byul. Izobr., No. 17 (2003).

  76. A. N. Kurchan and A. G. Kutateladze, Org. Lett., 4, 4129 (2002).

    Article  CAS  Google Scholar 

  77. S. R. Khafizova, Dis. Cand. Chem. Sci. [in Russian], Ufa (2003).

  78. V. R. Akhmetova, G. R. Nadyrgulova, Z. T. Niatshina, R. R. Khairullina, Z. A. Starikova, M. Yu. Antipin, R. V. Kunakova, and U. M. Dzhemilev, Heterocycles, 77, 45 (2009).

    Article  Google Scholar 

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Correspondence to V. R. Akhmetova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1443-1469, October, 2009.

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Akhmetova, V.R., Nadyrgulova, G.R., Niatshina, Z.T. et al. Cyclothiomethylation of primary amines with formaldehyde and hydrogen sulfide to nitrogen- and sulfur-containing heterocycles (review). Chem Heterocycl Comp 45, 1155–1176 (2009). https://doi.org/10.1007/s10593-010-0403-7

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