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Volumn 35, Issue 4, 1998, Pages 887-890

Boron-Containing Nucleosides. 1. Synthesis of the Novel Heterocycle 2-Benzyl-1,4-dihydro-1-hydroxythieno[3,2-c7] [1,5,2]diazaborin-3(2H)-one: A Thieno-fused 4-Borauracil

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EID: 1542606416     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570350417     Document Type: Article
Times cited : (6)

References (40)
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    • (1997) Advances in Boron Chemistry, Special Publication No. 201 , vol.201
    • Siebert, W.1
  • 2
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    • Royal Society of Chemistry, Cambridge, UK
    • For reviews of the synthesis and applications of boron compounds see: [a] Advances in Boron Chemistry, Special Publication No. 201, W. Siebert, ed, Royal Society of Chemistry, Cambridge, UK, 1997; [b] Current Topics in the Chemistry of Boron, Special Publication No. 143, G. W. Kabalka, ed, Royal Society of Chemistry, Cambridge, UK, 1994, pp 145-203; I. Ander, Heterocyclic Rings Containing Boron, Vol 1, Chapter 21, in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees, eds, Pergamon Press, Oxford, UK, 1984, pp 629-633; A. J. Fritsch, Borazaromatic Compounds, Vol 30, Chapter 7, in The Chemistry of Heterocyclic Compounds: Special Topics in Heterocyclic Chemistry, John Wiley & Sons, New York, 1977, pp 381-440; [e] M.J.S. Dewar, Heteroaromatic Boron Compounds, Vol 42, Chapter 23, in Advances in Chemistry: Boron-Nitrogen Chemistry, R. F. Gould, ed, American Chemical Society, Washington, DC, 1964, pp 227-250.
    • (1994) Current Topics in the Chemistry of Boron, Special Publication No. 143 , vol.143 , pp. 145-203
    • Kabalka, G.W.1
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    • Chapter 21, in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees, eds, Pergamon Press, Oxford, UK
    • For reviews of the synthesis and applications of boron compounds see: [a] Advances in Boron Chemistry, Special Publication No. 201, W. Siebert, ed, Royal Society of Chemistry, Cambridge, UK, 1997; [b] Current Topics in the Chemistry of Boron, Special Publication No. 143, G. W. Kabalka, ed, Royal Society of Chemistry, Cambridge, UK, 1994, pp 145-203; I. Ander, Heterocyclic Rings Containing Boron, Vol 1, Chapter 21, in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees, eds, Pergamon Press, Oxford, UK, 1984, pp 629-633; A. J. Fritsch, Borazaromatic Compounds, Vol 30, Chapter 7, in The Chemistry of Heterocyclic Compounds: Special Topics in Heterocyclic Chemistry, John Wiley & Sons, New York, 1977, pp 381-440; [e] M.J.S. Dewar, Heteroaromatic Boron Compounds, Vol 42, Chapter 23, in Advances in Chemistry: Boron-Nitrogen Chemistry, R. F. Gould, ed, American Chemical Society, Washington, DC, 1964, pp 227-250.
    • (1984) Heterocyclic Rings Containing Boron , vol.1 , pp. 629-633
    • Ander, I.1
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    • Chapter 7, in The Chemistry of Heterocyclic Compounds: Special Topics in Heterocyclic Chemistry, John Wiley & Sons, New York
    • For reviews of the synthesis and applications of boron compounds see: [a] Advances in Boron Chemistry, Special Publication No. 201, W. Siebert, ed, Royal Society of Chemistry, Cambridge, UK, 1997; [b] Current Topics in the Chemistry of Boron, Special Publication No. 143, G. W. Kabalka, ed, Royal Society of Chemistry, Cambridge, UK, 1994, pp 145-203; I. Ander, Heterocyclic Rings Containing Boron, Vol 1, Chapter 21, in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees, eds, Pergamon Press, Oxford, UK, 1984, pp 629-633; A. J. Fritsch, Borazaromatic Compounds, Vol 30, Chapter 7, in The Chemistry of Heterocyclic Compounds: Special Topics in Heterocyclic Chemistry, John Wiley & Sons, New York, 1977, pp 381-440; [e] M.J.S. Dewar, Heteroaromatic Boron Compounds, Vol 42, Chapter 23, in Advances in Chemistry: Boron-Nitrogen Chemistry, R. F. Gould, ed, American Chemical Society, Washington, DC, 1964, pp 227-250.
    • (1977) Borazaromatic Compounds , vol.30 , pp. 381-440
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  • 5
    • 77956701802 scopus 로고
    • Chapter 23, in Advances in Chemistry: Boron-Nitrogen Chemistry, R. F. Gould, ed, American Chemical Society, Washington, DC
    • For reviews of the synthesis and applications of boron compounds see: [a] Advances in Boron Chemistry, Special Publication No. 201, W. Siebert, ed, Royal Society of Chemistry, Cambridge, UK, 1997; [b] Current Topics in the Chemistry of Boron, Special Publication No. 143, G. W. Kabalka, ed, Royal Society of Chemistry, Cambridge, UK, 1994, pp 145-203; I. Ander, Heterocyclic Rings Containing Boron, Vol 1, Chapter 21, in Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees, eds, Pergamon Press, Oxford, UK, 1984, pp 629-633; A. J. Fritsch, Borazaromatic Compounds, Vol 30, Chapter 7, in The Chemistry of Heterocyclic Compounds: Special Topics in Heterocyclic Chemistry, John Wiley & Sons, New York, 1977, pp 381-440; [e] M.J.S. Dewar, Heteroaromatic Boron Compounds, Vol 42, Chapter 23, in Advances in Chemistry: Boron-Nitrogen Chemistry, R. F. Gould, ed, American Chemical Society, Washington, DC, 1964, pp 227-250.
    • (1964) Heteroaromatic Boron Compounds , vol.42 , pp. 227-250
    • Dewar, M.J.S.1
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  • 26
    • 1542739276 scopus 로고    scopus 로고
    • Synthesis of a endocyclic boron-containing nucleoside (BCN) is claimed in [20], but no references or details are given
    • Synthesis of a endocyclic boron-containing nucleoside (BCN) is claimed in [20], but no references or details are given.
  • 30
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    • Urea 2c was prepared by reduction of 2,3-O-isopropylidene-5-O-tert-butyldiphenylsiiyl-β-D-ribofuranosylazide to the corresponding amine followed by reaction with benzyl isocyanate; see J. Baddiley, J. G. Buchanan, R. Hodges, and J. F. Prescott, J. Chem. Soc., 4769 (1957). The azide was prepared via the corresponding chloride, which was prepared essentially by the method of R. S. Klein, H. Ohrui, and J. J. Fox, J. Carbohydr. Nucleosides Nucleotides, 1, 265 (1974), replacing trityl chloride with tert-butyldiphenylchlorosilane.
    • (1957) J. Chem. Soc. , pp. 4769
    • Baddiley, J.1    Buchanan, J.G.2    Hodges, R.3    Prescott, J.F.4
  • 31
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    • replacing trityl chloride with tert-butyldiphenylchlorosilane
    • Urea 2c was prepared by reduction of 2,3-O-isopropylidene-5-O-tert-butyldiphenylsiiyl-β-D-ribofuranosylazide to the corresponding amine followed by reaction with benzyl isocyanate; see J. Baddiley, J. G. Buchanan, R. Hodges, and J. F. Prescott, J. Chem. Soc., 4769 (1957). The azide was prepared via the corresponding chloride, which was prepared essentially by the method of R. S. Klein, H. Ohrui, and J. J. Fox, J. Carbohydr. Nucleosides Nucleotides, 1, 265 (1974), replacing trityl chloride with tert-butyldiphenylchlorosilane.
    • (1974) J. Carbohydr. Nucleosides Nucleotides , vol.1 , pp. 265
    • Klein, R.S.1    Ohrui, H.2    Fox, J.J.3
  • 37
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    • Chapter 9, in The Chemistry of Functional Groups: The Chemistry of the Azido Group, S. Patai, ed, John Wiley & Sons, New York
    • W. Lwowski, Acyl Azides, Chapter 9, in The Chemistry of Functional Groups: The Chemistry of the Azido Group, S. Patai, ed, John Wiley & Sons, New York, 1971, pp 503-554.
    • (1971) Acyl Azides , pp. 503-554
    • Lwowski, W.1
  • 39
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    • Chapter 3, in NMR of Newly Accessible Nuclei, Academic Press, New York
    • R. G. Kidd, Boron-11, Vol 2, Chapter 3, in NMR of Newly Accessible Nuclei, Academic Press, New York, 1983, pp 49-77.
    • (1983) Boron-11 , vol.2 , pp. 49-77
    • Kidd, R.G.1


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