Synthesis of aryldifluoromethylphosphonothioic acids from O,O-diethyl aryldifluoromethylphosphonothioates

Journal of Organic Chemistry

Volumn 65, Issue 18, 2000, Pages 5858-5861

  Yokomatsu, Tsutomu ^a   Takechi, Hiroaki ^a   Murano, Tetsuo ^a   Shibuya, Shiroshi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLDIFLUOROMETHYLPHOSPHONOTHIONATE DERIVATIVE; ARYLDIFLUOROMETHYLPHOSPHONOTHIONIC ACID; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; NOTE; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033828993     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000563t     Document Type: Note

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6. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
7. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
8. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
9. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
10. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
11. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
12. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
13. For the synthesis of 1,1-difluoromethylenephosphonic acids with significant activity: (a) Chambers, R. D.; Jaouhari, R.; O'Hagan, D. J. Chem. Soc., Chem. Commun. 1988, 1169. (b) Phillion, D. P.; Cleary, D. G. J. Org. Chem. 1992, 57, 2763. (c) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227. (d) Vinod, T. K.; Griffith, O. H.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193. (e) Martin, S. F.; Wong, Y.-L.; Wagman, A. S. J. Org. Chem. 1994, 59, 4821. (f) Matulic- Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563. (g) Halazy, S.; Ehrhard, A.; Eggenspiller, A.; Berges-Gross, V.; Danzin, C. Tetrahedron 1996, 52, 177 and references therein. (h) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495. (i) Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Wang, Q.; Ramachandran, C.; Hung, Z. Bioorg. Med. Chem. 1998, 6, 1457 and references therein. (j) Yokomatsu, T.; Hayakawa, Y.; Suemune, K.; Kihara, T.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 2833.
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42. PF = 95.3 Hz) appeared at δ 72.4.
43. We found that the diethyl ester 7a rapidly rearranged to the corresponding sodium S-ethyl phosphonothioate ii in good yield (80%) upon heating with sodium iodide (2 equiv) in 2-butanone in the absence of 3-iodopropene under reflux: (formula presented)
44. In these reactions, potassium salts of the starting 8a,d-f were recovered in 45-50% yield. No reactions occurred when the sodium salts 18a, d-f were submitted to the Pd-catalyzed deallylation conditions.