A simple synthesis of functionalized 2-amino-3-cyano-4-chromones by application of the N-hydroxybenzotriazole methodology

Arkivoc

Volumn 2006, Issue 10, 2006, Pages 28-34

  Athanasellis, Giorgos ^a   Melagraki, Georgia ^a   Afantitis, Antreas ^a   Makridima, Kalliopi ^a   Igglessi Markopoulou, Olga ^a  

^a NATIONAL TECHNICAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

Acylation; Chromones; Cyclization; N hydroxybenzotriazole

Indexed keywords

EID: 33244479407     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. (a) Miao, H.; Yang, Z. Org. Lett. 2000, 2, 1765 and refs. therein.
2. (b) Silva, A. M. S.; Pinto, D. C. G. A.; Cavaleiro, J. A. S.; Levai, A.; Patonay, T. Arkivoc 2004, 106.
3. (c) Levai, A. Arkivoc 2004, 15.
4. Valenti, P.; Bisi, A.; Rampa, A.; Belluti, F.; Gobbi, S.; Zampiron, A.; Carrara, M. Biorg. Med. Chem. 2000, 239.
5. Lim, L.-C.; Kuo, Y.-C.; Chou, C.-J. J. Nat. Prod. 2000, 63, 627.
6. Shi, Y. Q.; Fukai, T.; Sakagami, H.; Chang, W.-J.; Yang, P.-Q.; Wang, F.-P.; Nomura, T. J. Nat. Prod. 2001, 64, 181.
7. Larget, R.; Lockhart, B.; Renard, P.; Largeron, M. Biorg. Med. Chem. Lett. 2000, 10, 835.
8. Groweiss, A.; Cardellins, J. H.; Boyd, M. R. J. Nat. Prod. 2000, 63, 1537.
9. Deng, Y.; Lee, J. P.; Ramamonjy, M. T.; Synder, J. K.; Des Etages, S. A.; Kanada, D.; Synder, M. P.; Turner, C. J. J. Nat. Prod. 2000, 63, 1082.
10. Khan, I. A.; Avery, M. A.; Burandt, C. L.; Goins, D. K.; Mikell, J. R.; Nash, T. E.; Azadega, A.; Walker, L. A. J. Nat. Prod. 2000, 63, 1414.
11. Mori, K.; Audran, G.; Monti, H. Synlett 1998, 259.
12. Pietta, P. J. J. Nat. Prod. 2000, 63, 1035.
13. (a) Beecher, G. R. J. Nutr. 2003, 133, 3248S.
14. (b) Hoult, J. R. S.; Moroney, M. A.; Paya, M. Methods Enzymol. 1994, 234, 443.
15. Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
16. (a) Livingstone, R. In Rodd's Chemistry of Carbon Compounds; Coffey, S. Eds.; Elsevier, 1977; Vol. IVE, p 139.
17. (b) Riva, C.; De Toma, C.; Donadel, L.; Boi, C.; Pennini, R.; Motta, G.; Leonardi, A. Synthesis 1997, 2, 195.
18. (c) Borrell, J. I.; Teixido, J.; Schuler, E.; Michelotti, E. Tetrahedron Lett. 2001, 42, 5331.
19. (d) Prakash, O.; Kumar, R.; Sharma, D.; Bhardwaj, V. J. Ind. Chem. Soc. 2004, 81, 888.
20. (a) Allan, J.; Robinson, R. J. Chem. Soc. 1924, 125, 2192.
21. (b) Rossolin, V.; Lokskin, V.; Samat, A.; Guglielmetti, R. Tetrahedron 2003, 59, 7725.
22. (a) Walenzyk, T.; Carola, C.; Buchholz, H.; Konig, B. Tetrahedron 2005, 61, 7366.
23. (b) Hodgetts, K. J. Arkivoc 2001, 74.
24. (a) Baker, W. J. Chem. Soc. 1933, 1381.
25. (b) Mahal, H. S.; Venkataraman, K. J. Chem. Soc. 1934, 1767.
26. (c) Dunne, A. T. M.; Gowan, J. E.; Keane, J.; O'Kelly, B. M.; Sullivan, D. O.; Roche, M. M.; Ryan, P. M.; Wheeler, T. S. J. Chem. Soc. 1950, 1252.
27. (d) Muller, E.; Kalai, T.; Jeko, J.; Hideg, K. Synthesis 2000, 10, 1415.
28. (e) Ganguly, A. K.; Kaur, S.; Mahata, P. K.; Biswas, D.; Pramanik, B. N.; Chan, T. M. Tetrahedron Lett. 2005, 46, 4119.
29. Kumar, P.; Bodas, M. S. Org. Lett. 2000, 2, 3821.
30. (a) Davies, S. G.; Mobbs, B. E.; Goodwin, C. J. J. Chem. Soc., Perkin Trans 1 1987, 12, 2597.
31. (b) Kalinin, V. N.; Shostakovsky, M. V.; Ponomaryov, A. B. Tetrahedron Lett. 1990, 31, 4073.
32. (c) Torii, S.; Okumoto, H.; Xu, L. H.; Sadakane, M.; Shostakovsky, M. V.; Ponomaryov, A. B.; Kalinin, V. N. Tetrahedron 1993, 49, 6773.
33. Reddy, G. J.; Latha, D.; Rao, K. S. Heterocyclic Commun. 2004, 10, 279.
34. Ghosh, T.; Saha, S.; Bandyopadhya, C. Synthesis 2005, 11, 1845.
35. Brown, R. E.; Lustgarten, D. M. US Patent 3932466, 1976.
36. (a) Athanasellis, G.; Gavrielatos, E.; Igglessi-Markopoulou, O. Synlett 2001, 10, 1653.
37. (b) Athanasellis, G.; Igglessi-Markopoulou, O.; Markopoulos, J. Synlett 2002, 10, 1736.
38. (c) Athanasellis, G.; Gavrielatos, E.; Igglessi-Markopoulou, O. Bull. Chem. Soc. Jpn. 2002, 12, 2691.
39. (d) Athanasellis, G.; Detsi, A.; Proussis, K.; Igglessi-Markopoulou, O.; Markopoulos, J. Synthesis, 2003, 13, 2015.
40. (e) Athanasellis, G.; Melagraki, G.; Chatzidakis, H.; Afantitis, A.; Detsi, A.; Igglessi-Markopoulou, O.; Markopoulos, J. Synthesis, 2004, 11, 1775.
41. Buckle, D. R. J. Med. Chem. 1977, 20, 265.
42. (a) Nohara, I. J. Med. Chem. 1985, 28, 559.
43. (b) Ishiguro, T. Heterocycles 1981, 16, 733.