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Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones

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Abstract

Conditions for selective substitution for one chlorine atom in 2-(R,R′-amino)-4,6-dichloro-1,3,5-triazines with a hydroxide ion were elaborated. Spectral and calculation methods showed that the products formed are in the lactam form, i.e., have the structure of 4-chloro-6-(R,R′-amino)-1,3,5-triazin-2(1H)-ones.

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References

  1. H. M. LeBaron, J. E. McFarland and O. C. Burnside, in The Triazine Herbicides, Eds M. L. Homer, E. M. Janis, C. B. Orvin, Elsevier, San Diego, 2008, p. 1.

    Chapter  Google Scholar 

  2. H. Behrendt, J. Altschuh, S. Sixt, J. Gasteiger, R. Höllering and T. Kostka, Chemosphere, 1999, 38, 1811.

    Article  CAS  Google Scholar 

  3. K. Koizumi, N. Kuboyama, K. Tomono, A. Tanaka, A. Ohki, H. Kohno, K. Wakabayashi, P. Böger, Pestic. Sci., 1999, 55, 642.

    Article  CAS  Google Scholar 

  4. US Pat. 4102872; http://worldwide.espacenet.com/search-Results?DB=worldwide.espacenet.com&loca.

  5. R. Fink, C. Frenz, M. Thelakkat, H.-W. Schmidt, Macromolecules, 1997, 30, 8177.

    Article  CAS  Google Scholar 

  6. J. Z. Jan, B. H. Huang, J. J. Lin, Polymer, 2003, 44, 1003.

    Article  CAS  Google Scholar 

  7. A. D. Sagar, R. D. Shingte, P. P. Wadgaonkar, M. M. Salunkhe, Eur. Polym. J., 2001, 37, 1493.

    Article  CAS  Google Scholar 

  8. N. Baindur, N. Chadha, B. M. Brandt, D. Asgari, R. J. Patch, C. Schalk-HiHi, T. E. Carver, I. P. Petrounia, C. A. Baumann, H. Ott, C. Manthey, B. A. Springer, M. R. Player, J. Med. Chem., 2004, 48, 1717.

    Article  Google Scholar 

  9. E. Boven, M. M. Nauta, H. M. M. Schlüper, C. A. M. Erkelens, H. M. Pinedo, Cancer Chemoth. Pharm., 1986, 18, 124.

    Article  CAS  Google Scholar 

  10. E. A. H. Friedheim, J. Am. Chem. Soc., 1944, 66, 1775.

    Article  CAS  Google Scholar 

  11. M. H. V. Huynh, M. A. Hiskey, D. E. Chavez, D. L. Naud, R. D. Gilardi, J. Am. Chem. Soc., 2005, 127, 12537.

    Article  CAS  Google Scholar 

  12. J. C. Oxley, J. L. Smith, J. S. Moran, J. Energ. Mater., 2009, 27, 63.

    Article  CAS  Google Scholar 

  13. M. H. V. Huynh, M. A. Hiskey, C. J. Pollard, D. P. Montoya, E. L. Hartline, R. Gilardi, J. Energ. Mater., 2004, 22, 217.

    Article  CAS  Google Scholar 

  14. A. K. Sikder, N. Sikder, J. Hazard. Mater., 2004, 112, 1.

    Article  CAS  Google Scholar 

  15. A. A. Korkin, R. J. Bartlett, J. Am. Chem. Soc., 1996, 118, 12244.

    Article  CAS  Google Scholar 

  16. R. Budziarek, J. Chem. Soc. C., 1971, 74.

  17. M. Veirong, Kh. Minfen, N. P. Samoilova, M. V. Gorelik, Zh. Org. Khim., 1996, 32, 1593 [Russ. J. Org. Chem. (Engl. Transl.), 1996, 32, 1544].

    Google Scholar 

  18. E. M. Smolin, L. Rapoport, S-Triazines and Derivatives, Wiley, New York-London, 1959.

    Google Scholar 

  19. K. Matsui, J. Synth. Org. Chem Jpn, 1959, 17, 528.

    Article  CAS  Google Scholar 

  20. V. I. Mur, Usp. Khim., 1964, 33, 182 [Russ. Chem. Rev. (Engl. Transl.), 1964, 33, 92].

    Article  CAS  Google Scholar 

  21. K. Matsui, J. Synth. Org. Chem Jpn, 1972, 30, 19.

    Article  CAS  Google Scholar 

  22. J. M. E. Quirke, in Comprehensive Heterocyclic Chemistry, Eds A. R. Katritzky, C. W. Rees, Pergamon, Oxford, 1984, p. 457.

    Chapter  Google Scholar 

  23. D. Bartholomew, in Comprehensive Heterocyclic Chemistry II, Eds A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Pergamon, Oxford, 1996, p. 575.

    Chapter  Google Scholar 

  24. G. Giacomelli, A. Porcheddu, in Comprehensive Heterocyclic Chemistry III, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier, Oxford, 2008, p. 197.

    Chapter  Google Scholar 

  25. A. V. Shastin, T. I. Godovikova, B. L. Korsunskii, Usp. Khim., 2003, 72, 311 [Russ. Chem. Rev. (Engl. Transl.), 2003, 72, 279].

    Article  Google Scholar 

  26. T. Ueda, S. Toyoshima, I. Nakata, Pharm. Bull., 1953, 1, 252.

    Article  CAS  Google Scholar 

  27. S.-H. Kim, D. G. Bartholomew, L. B. Allen, R. K. Robins, G. R. Revankar, P. Dea, J. Med. Chem., 1978, 21, 883.

    Article  CAS  Google Scholar 

  28. A. Talebian, A. Ghiorghis, C. F. Hammer, E. A. Murril, F. Pallas, J. Heterocycl. Chem., 1992, 29, 979.

    Article  CAS  Google Scholar 

  29. R. A. Coxall, S. G. Harris, D. K. Henderson, S. Parsons, P. A. Tasker, R. E. P. Winpenny, J. Chem. Soc., Dalton Trans., 2000, 2349–2356.

  30. US Pat. 4246408; http://worldwide.espacenet.com/search-Results?DB=worldwide.espacenet.com&loca.

  31. Y. Wang, C. U. Pittman, S. Saebo, J. Org. Chem., 1993, 58, 3085.

    Article  CAS  Google Scholar 

  32. A. V. Shastin, T. I. Godovikova, S. P. Golova, V. S. Kuz’min, L. I. Khmel’nitskii, B. L. Korsunskii, Mendeleev Commun., 1995, 5, 17.

    Article  Google Scholar 

  33. G. Just, I. Pokorny, W. Pritzkow, J. Prakt. Chem., 1995, 337, 133.

    Article  CAS  Google Scholar 

  34. H. S. Mosher, F. C. Whitmore, J. Am. Chem. Soc., 1945, 67, 662.

    Article  CAS  Google Scholar 

  35. W. M. Pearlman, C. K. Banks, J. Am. Chem. Soc., 1948, 70, 3726.

    Article  CAS  Google Scholar 

  36. J. T. Thurston, J. R. Dudley, D. W. Kaiser, I. Hechenbleikner, F. C. Schaefer, D. Holm-Hansen, J. Am. Chem. Soc., 1951, 73, 2981.

    Article  CAS  Google Scholar 

  37. V. P. Wystrach, D. W. Kaiser, F. C. Schaefer, J. Am. Chem. Soc., 1955, 77, 5915.

    Article  CAS  Google Scholar 

  38. J. N. Ashley, S. S. Berg, R. D. MacDonald, J. Chem. Soc. (Res.), 1960, 4525.

  39. H. Koopman, J. Daams, Recl. Trav. Chim. Pays-Bas, 1958, 77, 235.

    Article  CAS  Google Scholar 

  40. N. Nohara, S. Sekiguchi, K. Matsui, J. Heterocycl. Chem., 1970, 7, 519.

    Article  CAS  Google Scholar 

  41. A. Kumar, K. Srivastava, S. Raja Kumar, M. I. Siddiqi, S. K. Puri, J. K. Sexana, P. M. S. Chauhan, Eur. J. Medel. Chem., 2011, 46, 676.

    Article  CAS  Google Scholar 

  42. N. Sunduru, M. Sharma, K. Srivastava, S. Rajakumar, S. K. Puri, J. K. Saxena, P. M. S. Chauhan, Biorg. Med. Chem., 2009, 17, 6451.

    Article  CAS  Google Scholar 

  43. M. Hedayatullah, C. Lion, A. B. Slimane, L. D. Conceiçao, I. Nachawati, Heterocycles, 1999, 51, 1891.

    Article  CAS  Google Scholar 

  44. K. Matsui, I. Sakamoto, J. Synth. Org. Chem. Jpn, 1960, 18, 175.

    Article  CAS  Google Scholar 

  45. H. E. Fierz-David, M. Matter, J. Soc. Dyers Colour., 1937, 53, 424.

    Article  CAS  Google Scholar 

  46. S. Horrobin, J. Chem. Soc. (Res.), 1963, 4130.

  47. N. V. Kozlova, D. F. Kutepov, D. N. Khokhlov, A. I. Krymova, Zh. Obshch. Khim., 1963, 33, 3303 [J. Gen. Chem. USSR (Engl. Transl.), 1963, 33, 3232].

    CAS  Google Scholar 

  48. A. F. Cockerill, G. L. O. Davies, D. M. Rackham, J. Chem. Soc., Perkin Trans. 2, 1974, 723.

  49. M. Hunter, A. Renfrew, J. A. Taylor, J. M. J. Whitmore, A. Williams, J. Chem. Soc., Perkin Trans. 2, 1994, 2389.

  50. T. N. Motorova (Bykhovskaya), O. N. Vlasov, I. A. Mel’nikova, N. N. Mel’nikov, Zh. Obshch. Khim., 1975, 45, 1847 [J. Gen. Chem. USSR (Engl. Transl.), 1975, 45, 1810].

    CAS  Google Scholar 

  51. R. Budziarek, P. Hampson, J. Chem. Soc. C., 1971, 1167.

  52. H. Hartmann, J. Liebscher, P. Czerney, Tetrahedron, 1985, 41, 5371.

    Article  CAS  Google Scholar 

  53. S. Kohra, K. Ueda, Y. Tominaga, Heterocycles, 1996, 43, 839.

    Article  CAS  Google Scholar 

  54. Y. Kihara, S. Kabashima, T. Yamasaki, T. Ohkawara, M. Furukawa, J. Heterocycl. Chem., 1990, 27, 1213.

    Article  Google Scholar 

  55. R. Bunnenberg, J. C. Jochims, H. Härle, Chem. Ber., 1982, 115, 3587.

    Article  CAS  Google Scholar 

  56. N. B. Hanna, M. Masojídková, P. Fiedler, A. Pískala, Collect. Czech. Chem. Commun., 1998, 63, 222.

    Article  CAS  Google Scholar 

  57. T. A. Riley, W. J. Hennen, N. K. Dalley, B. E. Wilson, R. K. Robins, J. Heterocycl. Chem., 1986, 23, 1709.

    Article  CAS  Google Scholar 

  58. S. N. Mikhailichenko, A. A. Chesnyuk, V. E. Zavodnik, S. I. Firgang, L. D. Konyushkin, V. N. Zaplishnyi, Khim. Geterotsikl. Soedin., 2002, 326 [Chem. Heterocycl. Compd. (Engl. Transl.), 2002, 38, 292].

    Google Scholar 

  59. J. K. Chakrabarti, D. E. Tupper, Tetrahedron, 1975, 31, 1879.

    Article  CAS  Google Scholar 

  60. B. Akteries, J. C. Jochims, Chem. Ber., 1986, 119, 1133.

    Article  CAS  Google Scholar 

  61. A. R. Katritzky, B. V. Rogovoy, V. Y. Vvedensky, N. Hebert, B. Forood, J. Org. Chem., 2001, 66, 6797.

    Article  CAS  Google Scholar 

  62. V. Kikelj, K. Julienne, P. Janvier, J.-C. Meslin, D. Deniaud, Synthesis, 2008, 3453.

  63. A. V. Shastin, T. I. Godovikova, B. L. Korsunskii, Khim. Geterotsikl. Soedin., 1999, 79 [Chem. Heterocycl. Compd. (Engl. Transl.), 1999, 35, 75].

    Google Scholar 

  64. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, T. V. Jr., K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, GAUSSIAN 03, Revision E.01, Gaussian, Inc., Wallingford (CT), 2004.

    Google Scholar 

  65. K. Yu. Suponitsky, Y. Liao, A. E. Masunov, J. Phys. Chem. A, 2009, 113, 10994.

    Article  CAS  Google Scholar 

  66. K. Yu. Suponitsky, A. E. Masunov, M. Yu. Antipin, Mendeleev Commun., 2009, 19, 311.

    Article  CAS  Google Scholar 

  67. R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendon Press, Oxford, 1990, 438 pp.

    Google Scholar 

  68. T. A. Keith, AIMAll (Version 09.04.23), 2009, http://aim.tkgristmill.com.

  69. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett., 1998, 285, 170.

    Article  CAS  Google Scholar 

  70. E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, E. Molins, Chem. Phys. Lett., 2001, 336, 457.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Samara State Technical University, 244 ul. Molodogvardeiskaya, 443100, Samara, Russian Federation

    V. V. Bakharev, A. A. Gidaspov, V. E. Parfenov, I. V. Ul’yankina, A. V. Zavodskaya & E. V. Selezneva

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. Yu. Suponitskii

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. B. Sheremetev

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  1. V. V. Bakharev
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  2. A. A. Gidaspov
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  3. V. E. Parfenov
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  4. I. V. Ul’yankina
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Correspondence to V. V. Bakharev or A. B. Sheremetev.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 97–109, January, 2012.

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Bakharev, V.V., Gidaspov, A.A., Parfenov, V.E. et al. Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones. Russ Chem Bull 61, 99–112 (2012). https://doi.org/10.1007/s11172-012-0015-8

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