Convenient routes to 2-aryl-2-fluoropropionic acids: Synthesis of monofluorinated analogues of (±)-ibuprofen, (±)-naproxen and related compounds

Tetrahedron

Volumn 52, Issue 39, 1996, Pages 12761-12774

  Goj, Olav ^a,b   Kotila, Sirpa ^a,c   Haufe, Günter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b STATE UNIVERSITY OF NEW YORK   (United States)

^c IT Center for Science   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORO 2 (6 METHOXY 2 NAPHTHYL)PROPIONIC ACID; NONSTEROID ANTIINFLAMMATORY AGENT; ORGANOFLUORINE DERIVATIVE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0030599254     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00758-2     Document Type: Article

References (54)

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22. 13 for some recent papers, cf.: J. D. Brown, Tetrahedron: Asymm. 1992, 3, 1551-1552; M. Garcia, C. del Campo, E. F. Llama, K. M. Sánchez-Montero, J. V. Sinisterra, Tetrahedron, 1993, 49, 8433-8440; T. Manimaran, T.-C. Wu, W. D. Klobucar, C. H. Kolich, G. P. Stahly, F. R. Fronczek, S. E. Watkins, Organometallics 1993, 12, 1467-1470; H. R. Sonawane, N. S. Bellur, D. G. Kulkarni, N.R. Ayyangar, Tetrahedron 1994, 50, 1243-1260; Calmes, J. Daunis, R. Jacquier, F. Natt, Tetrahedron 1994, 50, 6875-6880; P. S. Manchand, D. L. Coffen, P. S. Belica, F. Wong, H. S. Wong, L. Berger, Heterocycles 1994, 39, 833-845; R. Morrone, G. Nicolosi, A. Patti, M. Piattelli, Tetrahedron: Asymm. 1995, 6, 1773-1778; D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron 1995, 51, 12645-12660.
23. 13 for some recent papers, cf.: J. D. Brown, Tetrahedron: Asymm. 1992, 3, 1551-1552; M. Garcia, C. del Campo, E. F. Llama, K. M. Sánchez-Montero, J. V. Sinisterra, Tetrahedron, 1993, 49, 8433-8440; T. Manimaran, T.-C. Wu, W. D. Klobucar, C. H. Kolich, G. P. Stahly, F. R. Fronczek, S. E. Watkins, Organometallics 1993, 12, 1467-1470; H. R. Sonawane, N. S. Bellur, D. G. Kulkarni, N.R. Ayyangar, Tetrahedron 1994, 50, 1243-1260; Calmes, J. Daunis, R. Jacquier, F. Natt, Tetrahedron 1994, 50, 6875-6880; P. S. Manchand, D. L. Coffen, P. S. Belica, F. Wong, H. S. Wong, L. Berger, Heterocycles 1994, 39, 833-845; R. Morrone, G. Nicolosi, A. Patti, M. Piattelli, Tetrahedron: Asymm. 1995, 6, 1773-1778; D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron 1995, 51, 12645-12660.
24. 13 for some recent papers, cf.: J. D. Brown, Tetrahedron: Asymm. 1992, 3, 1551-1552; M. Garcia, C. del Campo, E. F. Llama, K. M. Sánchez-Montero, J. V. Sinisterra, Tetrahedron, 1993, 49, 8433-8440; T. Manimaran, T.-C. Wu, W. D. Klobucar, C. H. Kolich, G. P. Stahly, F. R. Fronczek, S. E. Watkins, Organometallics 1993, 12, 1467-1470; H. R. Sonawane, N. S. Bellur, D. G. Kulkarni, N.R. Ayyangar, Tetrahedron 1994, 50, 1243-1260; Calmes, J. Daunis, R. Jacquier, F. Natt, Tetrahedron 1994, 50, 6875-6880; P. S. Manchand, D. L. Coffen, P. S. Belica, F. Wong, H. S. Wong, L. Berger, Heterocycles 1994, 39, 833-845; R. Morrone, G. Nicolosi, A. Patti, M. Piattelli, Tetrahedron: Asymm. 1995, 6, 1773-1778; D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron 1995, 51, 12645-12660.
25. 13 for some recent papers, cf.: J. D. Brown, Tetrahedron: Asymm. 1992, 3, 1551-1552; M. Garcia, C. del Campo, E. F. Llama, K. M. Sánchez-Montero, J. V. Sinisterra, Tetrahedron, 1993, 49, 8433-8440; T. Manimaran, T.-C. Wu, W. D. Klobucar, C. H. Kolich, G. P. Stahly, F. R. Fronczek, S. E. Watkins, Organometallics 1993, 12, 1467-1470; H. R. Sonawane, N. S. Bellur, D. G. Kulkarni, N.R. Ayyangar, Tetrahedron 1994, 50, 1243-1260; Calmes, J. Daunis, R. Jacquier, F. Natt, Tetrahedron 1994, 50, 6875-6880; P. S. Manchand, D. L. Coffen, P. S. Belica, F. Wong, H. S. Wong, L. Berger, Heterocycles 1994, 39, 833-845; R. Morrone, G. Nicolosi, A. Patti, M. Piattelli, Tetrahedron: Asymm. 1995, 6, 1773-1778; D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron 1995, 51, 12645-12660.
26. 13 for some recent papers, cf.: J. D. Brown, Tetrahedron: Asymm. 1992, 3, 1551-1552; M. Garcia, C. del Campo, E. F. Llama, K. M. Sánchez-Montero, J. V. Sinisterra, Tetrahedron, 1993, 49, 8433-8440; T. Manimaran, T.-C. Wu, W. D. Klobucar, C. H. Kolich, G. P. Stahly, F. R. Fronczek, S. E. Watkins, Organometallics 1993, 12, 1467-1470; H. R. Sonawane, N. S. Bellur, D. G. Kulkarni, N.R. Ayyangar, Tetrahedron 1994, 50, 1243-1260; Calmes, J. Daunis, R. Jacquier, F. Natt, Tetrahedron 1994, 50, 6875-6880; P. S. Manchand, D. L. Coffen, P. S. Belica, F. Wong, H. S. Wong, L. Berger, Heterocycles 1994, 39, 833-845; R. Morrone, G. Nicolosi, A. Patti, M. Piattelli, Tetrahedron: Asymm. 1995, 6, 1773-1778; D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron 1995, 51, 12645-12660.
27. 13 for some recent papers, cf.: J. D. Brown, Tetrahedron: Asymm. 1992, 3, 1551-1552; M. Garcia, C. del Campo, E. F. Llama, K. M. Sánchez-Montero, J. V. Sinisterra, Tetrahedron, 1993, 49, 8433-8440; T. Manimaran, T.-C. Wu, W. D. Klobucar, C. H. Kolich, G. P. Stahly, F. R. Fronczek, S. E. Watkins, Organometallics 1993, 12, 1467-1470; H. R. Sonawane, N. S. Bellur, D. G. Kulkarni, N.R. Ayyangar, Tetrahedron 1994, 50, 1243-1260; Calmes, J. Daunis, R. Jacquier, F. Natt, Tetrahedron 1994, 50, 6875-6880; P. S. Manchand, D. L. Coffen, P. S. Belica, F. Wong, H. S. Wong, L. Berger, Heterocycles 1994, 39, 833-845; R. Morrone, G. Nicolosi, A. Patti, M. Piattelli, Tetrahedron: Asymm. 1995, 6, 1773-1778; D. P. G. Hamon, R. A. Massy-Westropp, J. L. Newton, Tetrahedron 1995, 51, 12645-12660.
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46. 30 I. Rivera, J. C. Colberg, J. A. Sonderquist, Tetrahedron Lett. 1992, 33, 6919-6922; R. A. Johnson, C. M. Hall, W. C. Krueger, H. C. Murray, Bioorg. Chem. 1973, 99, 100-104; Z.-J. Ni, N. W. Wai, X. Shi, Y.-L. Tang, M. C. Wang, T. Y. Luh, J. Org. Chem. 1991, 56, 4035-4042; G. Fraenkel, J. M. Geckle, J. Am. Chem. Soc. 1980, 56, 2869-2880; C. Fouquey, J. Jacques, G. Azadian-Boulanger, Eur. J. Med. Chem., Chim. Ther. 1978, 13, 303-308; K. Shishido, A. Yamashita, K. Hiroya, J. Chem. Soc., Perkin Trans, 1, 1990, 469-475.
47. 30 I. Rivera, J. C. Colberg, J. A. Sonderquist, Tetrahedron Lett. 1992, 33, 6919-6922; R. A. Johnson, C. M. Hall, W. C. Krueger, H. C. Murray, Bioorg. Chem. 1973, 99, 100-104; Z.-J. Ni, N. W. Wai, X. Shi, Y.-L. Tang, M. C. Wang, T. Y. Luh, J. Org. Chem. 1991, 56, 4035-4042; G. Fraenkel, J. M. Geckle, J. Am. Chem. Soc. 1980, 56, 2869-2880; C. Fouquey, J. Jacques, G. Azadian-Boulanger, Eur. J. Med. Chem., Chim. Ther. 1978, 13, 303-308; K. Shishido, A. Yamashita, K. Hiroya, J. Chem. Soc., Perkin Trans, 1, 1990, 469-475.
48. 30 I. Rivera, J. C. Colberg, J. A. Sonderquist, Tetrahedron Lett. 1992, 33, 6919-6922; R. A. Johnson, C. M. Hall, W. C. Krueger, H. C. Murray, Bioorg. Chem. 1973, 99, 100-104; Z.-J. Ni, N. W. Wai, X. Shi, Y.-L. Tang, M. C. Wang, T. Y. Luh, J. Org. Chem. 1991, 56, 4035-4042; G. Fraenkel, J. M. Geckle, J. Am. Chem. Soc. 1980, 56, 2869-2880; C. Fouquey, J. Jacques, G. Azadian-Boulanger, Eur. J. Med. Chem., Chim. Ther. 1978, 13, 303-308; K. Shishido, A. Yamashita, K. Hiroya, J. Chem. Soc., Perkin Trans, 1, 1990, 469-475.
49. 30 I. Rivera, J. C. Colberg, J. A. Sonderquist, Tetrahedron Lett. 1992, 33, 6919-6922; R. A. Johnson, C. M. Hall, W. C. Krueger, H. C. Murray, Bioorg. Chem. 1973, 99, 100-104; Z.-J. Ni, N. W. Wai, X. Shi, Y.-L. Tang, M. C. Wang, T. Y. Luh, J. Org. Chem. 1991, 56, 4035-4042; G. Fraenkel, J. M. Geckle, J. Am. Chem. Soc. 1980, 56, 2869-2880; C. Fouquey, J. Jacques, G. Azadian-Boulanger, Eur. J. Med. Chem., Chim. Ther. 1978, 13, 303-308; K. Shishido, A. Yamashita, K. Hiroya, J. Chem. Soc., Perkin Trans, 1, 1990, 469-475.
50. 30 I. Rivera, J. C. Colberg, J. A. Sonderquist, Tetrahedron Lett. 1992, 33, 6919-6922; R. A. Johnson, C. M. Hall, W. C. Krueger, H. C. Murray, Bioorg. Chem. 1973, 99, 100-104; Z.-J. Ni, N. W. Wai, X. Shi, Y.-L. Tang, M. C. Wang, T. Y. Luh, J. Org. Chem. 1991, 56, 4035-4042; G. Fraenkel, J. M. Geckle, J. Am. Chem. Soc. 1980, 56, 2869-2880; C. Fouquey, J. Jacques, G. Azadian-Boulanger, Eur. J. Med. Chem., Chim. Ther. 1978, 13, 303-308; K. Shishido, A. Yamashita, K. Hiroya, J. Chem. Soc., Perkin Trans, 1, 1990, 469-475.
51. 31 T. Kutsuma, I. Nagayama, T. Okazaki, T. Sakamoto, S. Akaboshi, Heterocycles 1977, 8, 397-401.
52. 32 G. M. Sheldrick, in: G. M. Sheldrick, C. Krüger, R. Goddard, Eds., Crystallographic Computing 3, Oxford University Press, Oxford, 1985, pp 175-189.
53. 33 G. M. Sheldrick, SHELXL-93, a program for crystal structure determination, University of Göttingen, 1993.
54. 34 E. Keller, SCHAKAL-92, a FORTRAN program for the graphic representation of molecular and crystallographic models, University of Freiburg, 1992.