Phosphonic acid analogs of diclofenac: An Arbuzov reaction of trimethylphosphite with an ortho-quinonoid intermediate

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2047-2050

  Mugrage, Ben ^a   Diefenbacher, Clive ^a   Somers, Joe ^a   Parker, David T ^a   Parker, Tonia ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Arbuzov reactions; Phosphonic acids and derivatives; Quinonoid compounds

Indexed keywords

DICLOFENAC DERIVATIVE; PHOSPHITE; PHOSPHONIC ACID DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DEALKYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION;

EID: 0034719701     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00111-8     Document Type: Article

References (17)

1. For the history of Diclofenac, see: Sallmann, A. Amer. J. Med. Suppl. 4B 1980, 29.
2. Kametani, T.; Takahashi, K.; VanLoc, C. Tetrahedron 1975, 31, 235.
3. (a) Guindon, Y.; Frenette, R.; Fortin, R.; Rokach, J. J. Org. Chem. 1983, 48, 1357.
4. (b) Porier, D.; Auger, S.; Merand, Y.; Simard, J,; Labrie, F. J. Med Chem. 1994, 37, 1115.
5. (c) Perrone, R.; Berardi, F.; Colabufo, N.; Leopoldo, M.; Tortorella, V.; Fiorentini, F.; Olgiati, V.; Ghiglier, A.; Govoni, S. J. Med. Chem. 1995, 38, 942.
6. MuraliDhar, T.; Borden, L.; Tyagarajan, S.; Smith, K.; Branchek, T.; Weinshank, R.; Gluchowski, C.; J. Med. Chem. 1995, 38, 942.
7. Kuroda, T.; Takahashi, M.; Kondo, K.; Iwasaki, T. J. Org. Chem. 1996, 61, 9560.
8. (a) As evidence for the formation of the ortho-quinonoid we have trapped this intermediate using a 4+2 cycloaddition reaction. The initial report of this work was presented at the 218th ACS National Meeting in New Orleans, Aug. 22-26, 1999, Abstract ORGN490; Tetrahydroquinolines Generated from Anthranilic Alcohols; Parker, D. T.; Mugrage, B.; Parker, T. S.; Li, H.; Boehm, C.
9. (b) Organic Syntheses Based on Named and Unnamed Reactions; Hassner, A.; Stumer, C.; Pergamon Press: Oxford, 1994; p. 5.
10. Moser, P.; Sallmann, A.; Wiesenberg, I. J. Med. Chem. 1990, 33, 2358.
11. Medicinal Chemistry Vol. 13-1: Antiinflammatory Agents, Chemistry and Pharmacology; Scherrer, R.; Ed.; Academic Press: New York, 1974; pp. 45-89.
12. (a) Brown, H.; Kim, S.; Krishnamurthy, S.; J. Org. Chem. 1980, 45, 1.
13. (b) Brown, H.; Kim, S. Synthesis 1977, 635.
14. -1.
15. Freeman, S.; Irwin, W.; Schwalbe, C. J. Chem. Soc., Perkin Trans. 2 1991, 263.
16. (a) Marshall, P.; Kulmacz, R.; Lands, W. J. Biol. Chem. 1986, 262, 3510.
17. (b) Wennogle, L.; Liang, H.; Quintavalla, J. FEBS Lett. 1995, 371, 315.