Synthesis of 6,7-diacylcoumarins via the transformation of a hydroxy into a carbonyl group

Synthetic Communications

Volumn 38, Issue 22, 2008, Pages 3996-4006

  Kotali, Antigoni ^a   Lafazanis, Ioannis S ^a   Harris, Philip A ^b  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b GLAXOSMITHKLINE   (United States)

Author keywords

6,7 diacyl 2H chromen 2 ones; Coumarins; Lead tetraacetate; N acylhydrazones; Oxidation; Transformation

Indexed keywords

ACETIC ACID DERIVATIVE; CARBONYL DERIVATIVE; COUMARIN DERIVATIVE; HYDRAZONE DERIVATIVE;

ARTICLE; CHEMICAL BOND; OXIDATION; SYNTHESIS;

EID: 54349114083     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802250911     Document Type: Article

References (21)

1. Weinmamm, I. In Coumarins: Biology, Applications and Modes of Actions; R. O'Kennedy, R. D. Thornes (Eds.); John Wiley: London, England, 1997; pp. 1-22.
2. (a) Riordan, D. J.; Daly, I. The growth-inhibiting properties of lactones. Ir. J. Med. Sci. 1954, 6, 157-161;
3. (b) Bose, P. K. On some biochemical properties of natural coumarins. J. Indian Chem. Soc. 1958, 58, 367-375.
4. Kostova, I. Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem.-Anti Cancer Agents 2005, 5, 29-46.
5. Tanaka, T.; Kumamoto, T.; Ishikawa, T. Enantioselective total synthesis of anti-HIV-1 active (+)-calanolide A through a quinine-catalyzed asymmetric intramolecular oxo-Michael addition. Tetrahedron Lett. 2000, 41, 10229-10232.
6. Jung, J.-C.; Kim, J.-C.; Park, O. S. A convenient one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1h)-one. Synth. Commun. 2001, 31, 1195-1200.
7. Jung, J.-C.; Kim, J.-C.; Park, O. S. Simple and cost effective syntheses of 4-hydroxycoumarin. Synth. Commun. 1999, 29, 3587-3595.
8. Musicki, B.; Periers, A.-M.; Laurin, P.; Ferroud, D.; Benedetti, Y.; Lachaud, S.; Chatreaux, F.; Haesslein, J.-L.; Iltis, A.; Pierre, C.; Khider, J.; Tessot, N.; Airault, M.; Demassey, J.; Dupuis-Hamelin, C.; Lassaigne, P.; Bonnefoy, A.; Vicat, P.; Klich, M. Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: Biological activity of RU79115. Bioorg. Med. Chem. Lett. 2000, 10, 1695-1699.
9. Soine, T. O. Naturally occurring coumarins and related physiological activities. J. Pharm. Sci. 1964, 53, 231-264.
10. Casley-Smith, J. R.; Casley-Smith, J. R. In Coumarins: Biology, Applications, and Modes of Actions; R. O'Kennedy, R. D. Thornes (Eds.); John Wiley: England, 1997; pp. 143-184.
11. Kostova, I. Synthetic and natural coumarins as antioxidants. Mini-Reviews in Med. Chem. 2006, 6, 365-374.
12. Lee, S.; Sivakumar, K.; Shin, W.-S.; Xie, W.; Wang, Q. Synthesis and anti-angiogenesis activity of coumarins derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 4596-4599.
13. Ivie, G. W.; Holt, D. L.; Ivey, M. C. Natural toxicants in human foods: Psoralens in raw cooked parsnip root. Science 1981, 213, 909-910.
14. Kleiner, H. E.; Vulimiri, S. V.; Miller, L.; Johnson, W. H: Whitman, C. P.; DiGiovanni, J. Oral administration of naturally occurring coumarins leads to altered phase I and II enzyme activities and reduced DNA adduct formation by polycyclic aromatic hydrocarbons in various tissues of SENCAR mice. Carcinogenesis 2001, 22, 73-82.
15. Prince, M.; Campbell, C. T.; Robertson, T. A.; Wells, A. J.; Kleiner, H. E. Naturally occurring coumarins inhibit 7,12-dimethylbenz[α]anthracene DNA adduct formation in mouse mammary gland. Carcinogenesis 2006, 29, 1204-1213.
16. Nam, N.-H.; Kim, Y.; You, Y.-J.; Hong, D.-H.; Ahn, B.-Z. Preliminary structure-antiangiogenic activity relationships of 4-senecioyloxymethyl-6,7- dimethoxy-coumarin. Bioorg. Med. Chem. Lett. 2002, 12, 2345-2348.
17. Kotali, A.; Lafazanis, I. S.; Harris, P. A. A novel and facile synthesis of 7,8-diacylcoumarins. Tetrahedron Lett. 2007, 48, 7181-7183.
18. Kotali, A. Reactions of hydrazones with lead tetraacetate. Curr. Org. Chem. 2002, 26, 965-985.
19. Abramov, M. A.; Dehaen, W. A novel approach to sulphide derivatives of furocoumarin natural products. Synthesis 2000, 1529-1531.
20. Katritzky, A. R.; Harris, P. A.; Kotali, A. Mechanism of the replacement of phenolic hydroxyl by carbonyl on lead tetraacetate treatment of o-hydroxylaryl ketone acylhydrazones. J. Org. Chem. 1991, 56, 5049-5051.
21. Kotali, A.; Harris, P. A. o-Diacylbenzenes in organic synthesis. A Review. Org. Prep. Proc. Int. 2003, 35, 583-601.