Preparation of 4-Hydroxy-3-Substituted, 2H-1-Benzopyran-2-ones and 2H-1-Benzothiopyran-2-ones from Carboxylic Esters and Methyl Salicylates or Methyl Thiosalicylate

Journal of Heterocyclic Chemistry

Volumn 34, Issue 4, 1997, Pages 1159-1162

  Davis, Sharon E ^a   Church, A Cameron ^a   Tummons, Rebecca C ^a   Beam, Charles F ^a  

^a School of Business and Economics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004604659     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340411     Document Type: Article

References (68)

1. Annually there are many citations dealing with clinical studies and some syntheses of these substituted coumarins. Reviews: [a] J. P. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol 3, Part 2B, A. R. Katritzky and C. W. Rees, eds, Board, Pergamon Press, New York, New York, 1984, pp 799-810; [b] R. Livingston, Rodd's Chemistry of Carbon Compounds, S. Coffey, ed, Elsevier, Amsterdam, 1977, Vol 10, Part E, pp 738, 767, 799, 816, 830, 861, 878, 919-920; [c] S. Wawzonek, Coumarins, Vol 2, Heterocyclic Compounds, R. C. Elderfield, ed, John Wiley and Sons, New York, New York, 1951; [d] R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, John Wiley and Sons, Inc, New York, New York, 1982; [e] M. Darbarwar and V. Sundramurthy, Synthesis, 337 (1982); [f] P. M. Dewick, in The Flavanoids: Advances in Research, J. B. Harborne and T. J. Mabry, eds, Chapman and Hall, London, 1982, p 535.
2. Annually there are many citations dealing with clinical studies and some syntheses of these substituted coumarins. Reviews: [a] J. P. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol 3, Part 2B, A. R. Katritzky and C. W. Rees, eds, Board, Pergamon Press, New York, New York, 1984, pp 799-810; [b] R. Livingston, Rodd's Chemistry of Carbon Compounds, S. Coffey, ed, Elsevier, Amsterdam, 1977, Vol 10, Part E, pp 738, 767, 799, 816, 830, 861, 878, 919-920; [c] S. Wawzonek, Coumarins, Vol 2, Heterocyclic Compounds, R. C. Elderfield, ed, John Wiley and Sons, New York, New York, 1951; [d] R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, John Wiley and Sons, Inc, New York, New York, 1982; [e] M. Darbarwar and V. Sundramurthy, Synthesis, 337 (1982); [f] P. M. Dewick, in The Flavanoids: Advances in Research, J. B. Harborne and T. J. Mabry, eds, Chapman and Hall, London, 1982, p 535.
3. Annually there are many citations dealing with clinical studies and some syntheses of these substituted coumarins. Reviews: [a] J. P. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol 3, Part 2B, A. R. Katritzky and C. W. Rees, eds, Board, Pergamon Press, New York, New York, 1984, pp 799-810; [b] R. Livingston, Rodd's Chemistry of Carbon Compounds, S. Coffey, ed, Elsevier, Amsterdam, 1977, Vol 10, Part E, pp 738, 767, 799, 816, 830, 861, 878, 919-920; [c] S. Wawzonek, Coumarins, Vol 2, Heterocyclic Compounds, R. C. Elderfield, ed, John Wiley and Sons, New York, New York, 1951; [d] R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, John Wiley and Sons, Inc, New York, New York, 1982; [e] M. Darbarwar and V. Sundramurthy, Synthesis, 337 (1982); [f] P. M. Dewick, in The Flavanoids: Advances in Research, J. B. Harborne and T. J. Mabry, eds, Chapman and Hall, London, 1982, p 535.
4. Annually there are many citations dealing with clinical studies and some syntheses of these substituted coumarins. Reviews: [a] J. P. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol 3, Part 2B, A. R. Katritzky and C. W. Rees, eds, Board, Pergamon Press, New York, New York, 1984, pp 799-810; [b] R. Livingston, Rodd's Chemistry of Carbon Compounds, S. Coffey, ed, Elsevier, Amsterdam, 1977, Vol 10, Part E, pp 738, 767, 799, 816, 830, 861, 878, 919-920; [c] S. Wawzonek, Coumarins, Vol 2, Heterocyclic Compounds, R. C. Elderfield, ed, John Wiley and Sons, New York, New York, 1951; [d] R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, John Wiley and Sons, Inc, New York, New York, 1982; [e] M. Darbarwar and V. Sundramurthy, Synthesis, 337 (1982); [f] P. M. Dewick, in The Flavanoids: Advances in Research, J. B. Harborne and T. J. Mabry, eds, Chapman and Hall, London, 1982, p 535.
5. Annually there are many citations dealing with clinical studies and some syntheses of these substituted coumarins. Reviews: [a] J. P. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol 3, Part 2B, A. R. Katritzky and C. W. Rees, eds, Board, Pergamon Press, New York, New York, 1984, pp 799-810; [b] R. Livingston, Rodd's Chemistry of Carbon Compounds, S. Coffey, ed, Elsevier, Amsterdam, 1977, Vol 10, Part E, pp 738, 767, 799, 816, 830, 861, 878, 919-920; [c] S. Wawzonek, Coumarins, Vol 2, Heterocyclic Compounds, R. C. Elderfield, ed, John Wiley and Sons, New York, New York, 1951; [d] R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, John Wiley and Sons, Inc, New York, New York, 1982; [e] M. Darbarwar and V. Sundramurthy, Synthesis, 337 (1982); [f] P. M. Dewick, in The Flavanoids: Advances in Research, J. B. Harborne and T. J. Mabry, eds, Chapman and Hall, London, 1982, p 535.
6. Annually there are many citations dealing with clinical studies and some syntheses of these substituted coumarins. Reviews: [a] J. P. Hepworth, in Comprehensive Heterocyclic Chemistry, Vol 3, Part 2B, A. R. Katritzky and C. W. Rees, eds, Board, Pergamon Press, New York, New York, 1984, pp 799-810; [b] R. Livingston, Rodd's Chemistry of Carbon Compounds, S. Coffey, ed, Elsevier, Amsterdam, 1977, Vol 10, Part E, pp 738, 767, 799, 816, 830, 861, 878, 919-920; [c] S. Wawzonek, Coumarins, Vol 2, Heterocyclic Compounds, R. C. Elderfield, ed, John Wiley and Sons, New York, New York, 1951; [d] R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins, John Wiley and Sons, Inc, New York, New York, 1982; [e] M. Darbarwar and V. Sundramurthy, Synthesis, 337 (1982); [f] P. M. Dewick, in The Flavanoids: Advances in Research, J. B. Harborne and T. J. Mabry, eds, Chapman and Hall, London, 1982, p 535.
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52. [9a] Acenocoumarin (acenocoumarol): 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one;
53. [b] cyclocumarol: 3,4-dihydro-2-methoxy-2-methyl-4-phenyl-2H,5H-pyrano[3,2-c][1]benzopyan-5-one;
54. [c] dicumarol (dicoumarin): 3,3′-methylene-bis[4-hydroxy-2H-1-benzopyran-2-one];
55. [d] tromexan (dicumacyl or B.O.E.A.); 4-hydroxy-α-(4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-2-oxo-2H-1-benzopyran- 3-acetic acid ethyl ester;
56. [e] phenprocoumon: 4-hydroxy-3-(1-phenylpropyl)-2H-1-benzopyran-2-one;
57. [f] coumadin (warfarin): 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one;
58. [g] 3,3′-methylene-bis[4-hydroxy-2H-1-benzothiopyran-2-one].
59. Collaborative study with Dr. Clyde R. Metz of this department and Dr. William T. Pennington of Clemson University.
60. Initially, biological screening will be coordinated and performed by Merck and Co., Inc. at several of their research facilities.
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66. High field multi-probe nmr (FT) will be available and performed in this department later in 1997 for inclusion in subsequent reports.
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