Preparation and optical properties of novel 3-alkoxycarbonyl aza- and diazacoumarins

Synthetic Communications

Volumn 40, Issue 20, 2010, Pages 3033-3045

  Féau, Clementine ^a   Klein, Emmanuel ^a   Kerth, Paul ^b   Lebeau, Luc ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b Preventor TBC GmbH   (Germany)

Author keywords

Azacoumarin; chromophore; coumarin; Knoevenagel condensation; Pechmann condensation

Indexed keywords

ALKYL GROUP; CARBONYL DERIVATIVE; COUMARIN DERIVATIVE; METHANOL;

ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; OPTICS; PECHMANN REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 77956898005     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903353747     Document Type: Article

References (25)

1. Murray, R. D. H.; Mendez, J.; Brown, S. A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry; John Wiley & Sons: New York, 1982; p. 227.
2. OKennedy, R.; Thornes, R. D. Coumarins: Biology, Applications, and Mode of Action; John Wiley & Sons: Chichester, 1997; p. 358.
3. Egan, D.; OKennedy, R.; Moran, E.; Cox, C.; Prosser, E.; Thornes, R. D. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds. Drug Metab. Rev. 1990, 22, 503-529.
4. Hoult, J. R. S.; Paya, M. Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol. 1996, 27, 713-722. (Pubitemid 26233347)
5. Lacy, A.; OKennedy, R. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer. Curr. Pharm. Design 2004, 10, 3797-3811.
6. Kostova, I. Coumarins as-inhibitors of HIV reverse transcriptase. Curr. HIV Res. 2006, 4, 347-363.
7. Hadjipavlou-Litina, D.; Kontogiorgis, C.; Pontiki, E.; Dakanali, M.; Akoumianaki, A.; Katerinopoulos, H. E. Anti-inflammatory and antioxidant activity of coumarins designed as potential fluorescent zinc sensors. J. Enzyme Inhib. Med. Chem. 2007, 22, 287-292.
8. Bissell, E. R.; Larson, D. K.; Croudace, M. C. Some 7-substituted-4- (trifluoromethyl)coumarin. J. Chem. Eng. Data 1981, 26, 348-350.
9. Specht, D. P.; Martic, P. A.; Farid, S. Ketocoumarins: A new class of triplet sensitizers. Tetrahedron 1982, 38, 1203-1211.
10. Zahradnik, M. The Production and Application of Fluorescent Brightening Agents; John Wiley & Sons: New York, 1992.
11. Samsonova, L. G.; Gadirov, R. M.; Ishchenko, V. V.; Khilya, O. V. Photophysical properties of coumarins in relation to the nature of their third and seventh substituents. Opt. Spectrosc. 2007, 102, 878-884.
12. Christie, R. M.; Morgan, K. M.; Islam, M. S. Molecular design and synthesis of N-arylsulfonated coumarin fluorescent dyes and their application to textiles. Dyes Pigments 2008, 76, 741-747.
13. Bredereck, H.; Simchen, G.; Santos, A. A. Synthesis in the heterocyclic series, IX: Syntheses and reactions of 4,6-disubstituted pyrimidine-5-aldehydes. Chem. Ber. 1967, 100, 1344-1352.
14. Moffet, R. B. Azacoumarins. J. Org. Chem. 1970, 35, 3596-3600.
15. Dejardin, J. V.; Lapiere, C. L. Synthèse dans le domaine des azacoumarines, I: Aza-7- coumarine et acide aza-7-coumarine carboxylique-3. Bull. Soc. Chim. Fr. 1978, 72-74.
16. Dejardin, J. V.; Lapiere, C. L. Synthèse dans le domaine des azacoumarines, II: Lacide aza-5-coumarine carboxylique-3 et ses dérivés. Bull. Soc. Chim. Fr. 1978, 75-82.
17. Schmidt, H. W.; Junek, H. Synthesis with nitriles, 50: Cyclization reactions to pyrano[ 3,2-c]pyridines and pyrano[3,2-c]quinolines with ethoxymethylenemalodinitrile and ethyl cyanoacetate. Monatsh. Chem. 1978, 109, 1075-1080.
18. Dejardin, J. V.; Lapiere, C. L. Synthèse dans le domaine des azacoumarines, III: Hydroxy-4-aza-5-coumarine et hydroxy-4-aza-7-coumarine. Bull. Soc. Chim. Fr. 1979, 289-298.
19. Kusar, M.; Svete, J.; Stanovnik, B. Diethyl N,N- dimethylaminomethylenemalonate in the synthesis of fused heterocyclic systems. J. Heterocycl. Chem. 1996, 33, 1041-1046.
20. Jones, G. The Knoevenagel condensations. In Organic Reactions; Wiley-Interscience: New York, 1967; vol.15, pp. 204-599.
21. Moffet, R. B. Azacoumarins. J. Org. Chem. 1970, 35, 3596-3600.
22. Sethna, S.; Phadke, R. The Pechmann reaction. Org. React. 1953, 7, 1-58.
23. Hurd, C. D.; Sherwood, L. T. J. The 1-amino-2-nitroethenes. J. Org. Chem. 1948, 13, 471-476.
24. Kato, Y.; Okada, S.; Tomimoto, K.; Mase, T. A facile bromination of hydroxyheteroarenes. Tetrahedron Lett. 2001, 42, 4849-4851.
25. Lebeau, L.; Olland, S.; Oudet, P.; Mioskowski, C. Rational design and synthesis of phospholipids for the two-dimensional crystallization of DNA gyrase, a key element in chromosome organization. Chem. Phys. Lipids 1992, 62, 93-103.