메뉴 건너뛰기




Volumn 60, Issue 12, 2003, Pages 2677-2684

Synthesis of 2H-1,2,3-triazolo 14,5-d]pyrimidine-5,7-diones from uracils using cyclization reaction of β-azo-α,β-unsaturated sulfilimines

Author keywords

[No Author keywords available]

Indexed keywords

2H 1,2,3 TRIAZOLO[4,5 D]PYRIMIDINE 5,7 DIONE; AZO COMPOUND; BETA AZO ALPHA,BETA UNSATURATED SULFILIMINE; DIAZONIUM COMPOUND; N (5 AZOURACIL 6 YL)DIPHENYLSULFILIMINE; N (URACIL 6 YL)DIPHENYSULFILIMINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL; URACIL DERIVATIVE;

EID: 0345282997     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-03-9884     Document Type: Article
Times cited : (10)

References (15)
  • 2
    • 33847089781 scopus 로고
    • T. L. Gilchrist and C. J. Moody, Chem. Rev., 1977, 77, 409; I. V. Koval, Sulfur Rep., 1993, 14, 149.
    • (1993) Sulfur Rep. , vol.14 , pp. 149
    • Koval, I.V.1
  • 3
    • 37049094978 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 2166
    • Gilchrist, T.L.1    Harris, C.J.2    Hawkins, D.G.3    Moody, C.J.4    Rees, C.W.5
  • 4
    • 0000635721 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1977) Bull. Chem. Soc. Jpn. , vol.50 , pp. 1793
    • Fuchigami, T.1    Odo, K.2
  • 5
    • 0011425554 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1977) Heterocycles , vol.8 , pp. 109
    • Tomimatsu, Y.1    Satoh, K.2    Sakamoto, M.3
  • 6
    • 0011518015 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1976) Bull. Chem. Soc. Jpn. , vol.49 , pp. 3124
    • Yoshida, H.1    Taketani, H.2    Ogata, T.3    Inokawa, S.4
  • 7
    • 37049112497 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1976) J. Chem. Soc., Perkin Trans. 1 , pp. 2161
    • Gilchrist, T.L.1    Harris, C.J.2    King, F.D.3    Peek, M.E.4    Rees, C.W.5
  • 8
    • 0000341461 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 2811
    • Ketcha, D.M.1    Abou-Gharbia, M.2    Smith, F.X.3    Swern, D.4
  • 9
    • 0001215371 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1973) J. Org. Chem. , vol.38 , pp. 4324
    • Tamura, Y.1    Sumoto, K.2    Matsushima, H.3    Taniguchi, H.4    Ikeda, M.5
  • 10
    • 0002936412 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1974) Chem. Lett. , pp. 247
    • Fuchigami, T.1    Odo, K.2
  • 11
    • 37049127599 scopus 로고
    • T. L. Gilchrist, C. J. Harris, D. G. Hawkins, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2166; T. Fuchigami and K. Odo, Bull. Chem. Soc. Jpn., 1977, 50, 1793; Y. Tomimatsu, K. Satoh, and M. Sakamoto, Heterocycles, 1977, 8, 109; H. Yoshida, H. Taketani, T. Ogata, and S. Inokawa, Bull. Chem. Soc. Jpn., 1976, 49, 3124; T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peek, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1976, 2161; D. M. Ketcha, M. Abou-Gharbia, F. X. Smith, and D. Swern, Tetrahedron Lett., 1983, 24, 2811; Y. Tamura, K. Sumoto, H. Matsushima, H. Taniguchi, and M. Ikeda, J. Org. Chem., 1973, 38, 4324; T. Fuchigami and K. Odo, Chem. Lett., 1974, 247; T. L. Gilchrist, C. J. Moody, and C. W. Rees, J. Chem. Soc., Perkin Trans. 1, 1975, 1964.
    • (1975) J. Chem. Soc., Perkin Trans. 1 , pp. 1964
    • Gilchrist, T.L.1    Moody, C.J.2    Rees, C.W.3
  • 12
    • 0037049302 scopus 로고    scopus 로고
    • N. Matsumoto and M. Takahashi, Tetrahedron, 2002, 58, 10073. The sulfilimine (1) was prepared from readily available 6-chloro-1,3-dimethyluracil and S,S-diphenylsulfilimine, while it was difficult to prepare 6-chloro-1,3-unsubstituted uracil.
    • (2002) Tetrahedron , vol.58 , pp. 10073
    • Matsumoto, N.1    Takahashi, M.2
  • 13
    • 84943402961 scopus 로고
    • ed. by A. R. Katritzky and C. W. Rees, Pergamon Press Ltd., Oxford
    • H. Wamhoff, "Comprehensive Heterocyclic Chemistry", Vol 5, ed. by A. R. Katritzky and C. W. Rees, Pergamon Press Ltd., Oxford, 1984, pp. 669-732.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.5 , pp. 669-732
    • Wamhoff, H.1
  • 14
    • 0002276684 scopus 로고
    • ed. by A. R. Katritzky and A. J. Boulton, Academic Pres, Inc., New York
    • T. L. Gilchrist and G. E. Gymer, "Advances in Heterocyclic Chemistry", Vol. 16, ed. by A. R. Katritzky and A. J. Boulton, Academic Pres, Inc., New York, 1974, pp. 33-85.
    • (1974) Advances in Heterocyclic Chemistry , vol.16 , pp. 33-85
    • Gilchrist, T.L.1    Gymer, G.E.2
  • 15
    • 33751131646 scopus 로고    scopus 로고
    • ed. by A. R. Katritzky, Academic Press, Inc., New York
    • E. S. H. El Ashry and N. Rashed, "Advances in Heterocyclic Chemistry", Vol. 71, ed. by A. R. Katritzky, Academic Press, Inc., New York, 1998, pp. 57-114.
    • (1998) Advances in Heterocyclic Chemistry , vol.71 , pp. 57-114
    • El Ashry, E.S.H.1    Rashed, N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.