Synthesis and reactivity of 6-methyl-4H-furo[3,2c]pyran-3,4-dione

Journal of Heterocyclic Chemistry

Volumn 48, Issue 1, 2011, Pages 31-37

  Hikem Oukacha, Djamila ^a   Rachedi, Yahïa ^a   Hamdi, Maamar ^a   Silva, Artur M S ^b  

^a UNIVERSITY OF SCIENCES AND TECHNOLOGY HOUARI BOUMEDIENE   (Algeria)

^b UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

3 BROMOACETYL 4 HYDROXY 6 METHYL 2H PYRAN 2 ONE; 6 METHYL 4H FURO[3,2C]PYRAN 3,4 DIONE; ACETIC ACID; ACETOPHENONE DERIVATIVE; BENZALDEHYDE DERIVATIVE; DEHYDROACETIC ACID; DITHIZONE; ESTER DERIVATIVE; THIOAMIDE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; CHEMICAL REACTION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS;

EID: 79251570580     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.490     Document Type: Article

References (51)

1. Bartels-Keith, J. R., J Chem Soc 1960, 1662.
2. Miyakado, M.,;, Inoue, S.,;, Tanabe, Y.,;, Watanabe, K.,;, Ohno, N.,;, Yoshioka, H.,;, Mabry, T., J Chem Lett 1982, 1539.
3. Akizawa, T.,;, Yasuhara, T.,;, Azuma, H.,;, Nakajima, T., Biomed Res 1985, 6, 437.
4. Azuma, S.,;, Sekizaki, S., Akizawa, T.,;, Yasuhara, T.,;, Nakajima, T., J Pharm Pharmacol 1986, 38, 388.
5. Cutler, H. G.,;, Jacyno, J. M., Agric Biol Chem 1991, 55, 2629.
6. Rasoanaivo, P.,;, Galeffi, G.,;, Multari, G.,;, Nicoletti, M.,;, Capolongo, L., Gazz Chim Ital 1993, 123, 539.
7. Steyn, P. S.,;, van Heerden, F. R., Nat Prod Rep 1998, 15, 397.
8. Collie, J. N., J Chem Soc 1891, 77, 973.
9. Altomare, C.,;, Perrone, G.,;, Zonno, M. C.,;, Evidente, A.,;, Pengue, R.,;, Fanti, F.,;, Polonelli, L., J Nat Prod 2000, 63, 1131.
10. Altomare, C.,;, Pengue, R.,;, Favilla, M.,;, Evidente, A.,;, Visconti, A., J Agric Food Chem 2004, 52, 2997.
11. Murray, R. D. H.,;, Méndez, J.,;, Brown, S. A., The Natural Coumarins: Occurrence, Chemistry and Biochemistry; Wiley-Interscience: New York, 1982.
12. Fahr, E., Pharmazeutishe Zeitung 1982, 127, 163.
13. Rehse, K.,;, Schinkel, W.,;, Siemann, U., Arch Pharm (Weinheim, Ger) 1980, 313, 344.
14. Purushothaman, K. K.,;, Sarada, A.,;, Connolly, J. D., Indian J Chem 1984, 23, 611.
15. El Abbassi, M.,;, Essassi, E. M.,;, Fifani, J., Tetrahedron Lett 1987, 28, 1389.
16. Rachedi, Y.,;, Hamdi, M.,;, Speziale, V., Synth Commun 1989, 19, 3427.
17. Kherfi, H. N.,;, Hamdi, M.,;, Speziale, V., J Heterocycl Chem 1990, 27, 1401.
18. Nedjar-Kolli, B.,;, Hamdi, M.,;, Pecher, J., Synth Commun 1990, 20, 1579.
19. Rachedi, Y.,;, Hamdi, M.,;, Sakellariou, R.,;, Speziale, V., Synth Commun 1991, 21, 1189.
20. Hernández-Galán, R.,;, Salvá, J.,;, Massanet, G. M.,;, Collado, I. G., Tetrahedron 1993, 49, 1701.
21. Bendaas, A.,;, Hamdi, M.,;, Sellier, N., J Heterocycl Chem 1999, 36, 1291.
22. Boutemeur-Kheddis, B.,;, Hamdi, M.,;, Sellier, N.,;, Silva, A. M. S., J Heterocycl Chem 2001, 38, 227.
23. Makhloufi-Chebli, M.,;, Hamdi, M.,;, Silva, A. M. S.,;, Duval, O.,;, Helesbeux J.-J., J Heterocycl Chem 2009, 46, 18.
24. (a), Kimpe, N. De.,;, Verhé, R., In The Chemistry of a-Haloketones, a-Haloaldeydes, a-Haloimines, Updates from the Chemistry of Functional Groups;, Patai, S.,;, Rapoport, Z, Eds.; Wiles: Chichester, 1988; p 1
25. (b), Erian, A. W.,;, Sherif, S. M.,;, Gaber, H. M., Molecules 2003, 8, 793.
26. Harris, T. M.,;, Harris, C. M.,;, Brush, C. K., J Org Chem 1970, 35, 1329.
27. Kumar, A.,;, Prakash, R.,;, Singh, S. P., Synth Commun 2005, 35, 461.
28. Prakash, R.,;, Kumar, A.,;, Singh, S. P.,;, Aggarwal, R.,;, Prakash, O., Indian J Chem 2007, 46B, 1713.
29. Reddy, G. S.,;, Sucheta, K.,;, Rao, N. R., Indian J Heterocycl Chem 1992, 2, 95.
30. Briel, D.,;, Askar, G. B.,;, Ortwein, J.,;, Unverferth, K., Pharmazie 2009, 64, 477.
31. Stephan, J. F.,;, Marcus, E., J Org Chem 1969, 34, 2527.
32. Hantzsch, A.,;, Weber, J. H., Ber Dsch Chem Ges 1887, 20, 3118.
33. Dean, F. M., In Naturally Occurring Oxygen Ring Compounds, 2nd ed.; Butterworths: London, 1963; p 176.
34. Wawzonek, O., In Heterocyclic Compounds; Wiley: New York, 1975; p 173.
35. Brown, M. D.,;, Gillon, D. W.,;, Meakins, G. D.,;, Whithan, G. A., J Chem Soc, Chem Commun 1982, 444.
36. Fuchigami, T.,;, Yeh, M. Y.,;, Nonaka, T.,;, Tien, H., J Bull Chem Soc Jpn 1983, 56, 3851.
37. Fuchigami, T.,;, Nonaka, T., J Org Chem 1983, 48, 3340.
38. Khazi, I. M.,;, Mahajanshetti, C. S., Monatsh Chem 1995, 126, 759.
39. Kidwai, M.,;, Kumar, R., Gazz Chim Ital 1997, 127, 263.
40. Kasmi, S.,;, Hamelin, J.,;, Benhaoua, H., Tetrahedron Lett 1998, 39, 8093.
41. Binu, R.,;, Thomas, K. K.,;, Jenardanan, G. C.,;, Rajasekharan, K. N., Org Prep Proced Int 1998, 30, 93.
42. Demirayak, S.,;, Karaburun, A. C.,;, Mohsen, U. A.,;, Benkli, K.,;, Guven, K., Acta Pharm Turc 1999, 41, 78.
43. Rudolph, J., Tetrahedron 2000, 56, 3161.
44. Suni, M. M.,;, Nair, V. A.,;, Joshua, C. P., Synlett 2001, 409.
45. Dovlatyan, V. V.,;, Eliazyan, K. A.,;, Pivazyan, V. A.,;, Ghazaryan, E. A.,;, Engoyan, A. P.,;, Grigoryan, R. T.,;, Mirzoyan, R. G., Chem Heterocycl Compd 2000, 36, 593.
46. Park, K.-J.,;, Bae, S. K., J Korean Ind Eng Chem 2007, 18, 326.
47. Tomika, Y.,;, Kabachima, S.,;, Okawara, T.,;, Yamasaki, T.,;, Furukawa, M., J Heterocycl Chem 1990, 27, 707.
48. Busby, R. E.,;, Doniney, T. W., J Chem Soc Perkin Trans 2 1980, 2, 890.
49. Pelter, A.,;, Ward, R. S.,;, Heller, H. G., J Chem Soc Perkin Trans 1 1979, 328.
50. Ur-Rahman, A.,;, Choudhary, M. I.,;, Hayat, S.,;, Khan, A. M.,;, Ahmed, A., Chem Pharm Bull 2001, 49, 105.
51. Venkateswarlu, S.,;, Panchagnula, G. K.,;, Gottumukkala, A. L.,;, Subbaraju, G. V., Tetrahedron 2007, 63, 6909.