Synthesis of heteroaryl 1,2-diketones

Journal of Organic Chemistry

Volumn 70, Issue 8, 2005, Pages 3271-3274

  Katritzky, Alan R ^a   Zhang, Dazhi ^a,b   Kirichenko, Kostyantyn ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; OXIDATION; OXYGEN; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

HETEROARYL 1,2-DIKETONES; SODIUM BICARBONATE;

KETONES;

2 (1H BENZOTRIAZOL 1 YL) 1 (2 FURYL) 2 (2 PYRIDINYL) 1 ETHENOL; 2 (1H BENZOTRIAZOL 1 YL) 1 (2 FURYL) 2 (3 PYRIDINYL) 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 1 (2 FURYL) 2 PHENYL 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 1 (2 METHYL 1,3 THIAZOL 4 YL) 2 PHENYL 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 1 (2 METHYL 1H INDOL 3 YL) 1 PHENYL 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 2 (1 METHYL 1H INDOL 3 YL) 1 (2 METHYL 1,3 THIAZOL 4 YL) 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 2 (1 METHYL 1H INDOL 3 YL) 1 (4 PYRIDINYL) 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 2 (2 FURYL) 1 (2 THIENYL) 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 2 (2 FURYL) 1 (4 PYRIDINYL) 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 2 PHENYL 1 (2 THIENYL) 1 ETHANONE; 2 (1H BENZOTRIAZOL 1 YL) 2 PHENYL 1 (4 PYRIDINYL) 1 ETHANONE; 2 (2H BENZOTRIAZOL 2 YL) 2 (2 FURYL) 1 (2 THIENYL) 1 ETHANONE; DIKETONE; HETEROARYL 1,2 DIKETONE; METHYL 3 [2 (1H BENZOTRIAZOL 1 YL) 2 PHENYLACETYL]BENZOATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SYNTHESIS;

EID: 17444387440     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0477998     Document Type: Article

References (52)

1. (a) Fitzi, K. Ger. Pat. 2221546, 1972; US Pat. 3929807, 1975; Chem. Abstr. 1973, 78, 58428.
2. (b) Kozlov, N. S.; Shmanal, G. S. Chem. Heterocycl. Compd. (Engl. Transl.) 1974, 974.
3. (c) Cremlyn, R. J.; Lynch, J. M.; Swinbourne, F. J. Phosphorus Sulfur 1991, 57, 173.
4. (d) Tong, L.; Ho, D. M.; Vogelaar, N. J.; Schutt, C. E.; Pascal, R. A., Jr. Tetrahedron Lett. 1997, 38, 7.
5. (e) Barta, T. E.; Stealey, M. A.; Collins, P. W.; Weier, R. M. Bioorg. Med. Chem. Lett. 1998, 8, 3443.
6. (f) Bark, T.; Weyhermüller, T.; Heirtzler, F. Chem. Commun. 1998, 1475.
7. (g) Heirtzler, F. R. Synlett 1999, 8, 1203.
8. (h) Collis, A. J.; Foster, M. L.; Halley, F.; Maslen, C.; McLay, I. M.; Page, K. M.; Redford, E. J.; Souness, J. E.; Wilsher, N. E. Bioorg. Med. Chem. Lett. 2001, 11, 693.
9. (i) Chang, L. L.; Sidler, K. L.; Cascieri, M. A.; de Laszlo, S.; Koch, G.; Li, B.; MacCoss, M.; Mantlo, N.; O'Keefe, S.; Pang, M.; Rolando, A.; Hagmann, W. K. Bioorg. Med. Chem. Lett. 2001, 11, 2549.
10. (j) Heirtzler, F.; Neuburger, M.; Kulike, K. J. Chem. Soc., Perkin Trans. 1 2002, 809.
11. (k) McKenna, J. M.; Halley, F.; Souness, J. E.; McLay, I. M.; Pickett, S. D.; Collis, A. J.; Page, K.; Ahmed, I. J. Med. Chem. 2002, 45, 2173.
12. Buehler, C. A.; Harris, J. O.; Arendale, W. F. J. Am. Chem. Soc. 1950, 72, 4953.
13. (a) Fischer, E. Justus Liebigs Ann. Chem. 1882, 211, 214.
14. (b) Buehler, C. A.; Harris, J. O. J. Am. Chem. Soc. 1950, 72, 5015.
15. (c) Katritzky, A. R.; Lang, H.; Wang, Z.; Zhang, Z.; Song, H. J. Org. Chem. 1995, 60, 7619.
16. Heirtzler, F. R.; Neuburger, M.; Zehnder, M.; Constable, E. C. Liebigs Ann./Recueil 1997, 297.
17. Chang, H. S.; Woo, J. C.; Lee, K. M.; Ko, Y. K.; Moon, S.-S.; Kim, D.-W. Synth. Commun. 2002, 32, 31.
18. Akiba, K.; Ohnari, H.; Ohkata, K. Chem. Lett. 1985, 10, 1577.
19. Walsh, C. J.; Mandal, B. K. J. Org. Chem. 1999, 64, 6102.
20. Yusubov, M. S.; Zholobova, G. A.; Vasilevsky, S. F.; Tretyakov, E. V.; Knight, D. W. Tetrahedron 2002, 58, 1607.
21. Buehler, C. A.; Addleburg, J. W.; Glenn, D. M. J. Org. Chem. 1955, 20, 1350.
22. Andrews, I. P.; Lewis, N. J.; McKillop, A.; Wells, A. S. Heterocycles 1994, 38, 713.
23. Tymonko, S. A.; Nattier, B. A.; Mohan, R. S. Tetrahedron Lett. 1999, 40, 7657.
24. Rao, T. V.; Dongre, R. S.; Jain, S. L.; Sain, B. Synth. Commun. 2002, 32, 2637.
25. Mitchell, R. H.; Iyer, V. S. Tetrahedron Lett. 1993, 34, 3683.
26. Sheldrake, P.; Tyrrell, E.; Mintias, S.; Shahid, I. Synth. Commun. 2003, 33, 2263.
27. (a) Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
28. (b) Katritzky, A. R.; Kirichenko, K.; Ji, Y.; Steel, P. J.; Karelson, M. Arkivoc 2003, vi, 49.
29. (c) Katritzky, A. R.; Kirichenko, K.; Mohapatra, P. P.; Prakash, I. Arkivoc 2004, iii, 22.
30. (d) Katritzky, A. R.; Kirichenko, K.; Hür, D.; Zhao, X.; Ji, Y.; Steel, P. J. Arkivoc 2004, vi, 27.
31. (a) Felix, A. M.; Fryer, R. I.; Sternbach, L. H. US Pat. 3546212, 1970; Chem. Abstr. 1971, 74, 112062.
32. (b) Archer, G. A.; Kalish, R. I.; Ning, R. Y.; Sluboski, B. C.; Stempel, A.; Steppe, T. V.; Sternbach, L. H. J. Med. Chem. 1977, 20, 1312.
33. (c) Sauter, F.; Stanetty, P.; Mesbah, A. J. Chem. Res., Synop. 1977, 186.
34. Yin, Z.; Zhang, Z.; Kadow, J. F.; Meanwell, N. A.; Wang, T. J. Org. Chem. 2004, 69, 1364.
35. Hamdouchi, C.; Sanchez-Martinez, C.; Gruber, J.; del Prado, M.; Lopez, J.; Rubio, A.; Heinz, B. A. J. Med. Chem. 2003, 46, 4333.
36. (a) Haider, N.; Heinisch, G.; Moshuber, J. Heterocycles 1994, 38, 125.
37. (b) Donetty, A.; Boniardi, O.; Ezhaya, A. Synthesis 1980, 1009.
38. (c) Kulp, S. S.; McGee, M. J. J. Org. Chem. 1983, 48, 4097.
39. (d) Hermann, C. K. F.; Sachdeva, Y. P.; Wolfe, J. F. J. Heterocyd. Chem. 1987, 24, 1061.
40. (e) Heinisch, G.; Langer, T. J. Heterocycl. Chem. 1993, 30, 1685.
41. (f) Heinisch, G.; Holzer, W.; Langer, T.; Lukavsky, P. Heterocycles 1988, 43, 151.
42. Kornblum, N.; Powers, J. W.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O.; Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562.
43. Kornblum, N.; Jones, W. J.; Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113.
44. Katritzky, A. R.; Toader, D. J. Am. Chem. Soc. 1997, 119, 9321.
45. Katritzky, A. R.; Xie, L.; Cundy, D. Synth. Commun. 1995, 25, 539.
46. Katritzky, A. R.; Yao, G.; Rachwal, S. J. Heterocycl. Chem. 1994, 31, 757
47. Katritzky, A. R.; Zhang, G.-F.; Pernak, J.; Fan, W.-Q. Heterocycles 1993, 36, 1253.
48. (a) Katritzky, A. R.; Gordeev, M. F.; Greenhill, J. V.; Steel, P. J. J. Chem. Soc., Perkin Trans. 1 1992, 1111.
49. (b) Katritzky, A. R.; Serdyuk, L.; Xie, L.; Ghiviriga, I. J. Org. Chem. 1997, 62, 6215.
50. (c) Katritzky, A. R.; Abdel-Fattah, A. A. A.; Tymoshenko, D. O.; Belyakov, S. A. Synthesis 1999, 1437.
51. Katritzky, A. R.; Wang, J.; Karodia, N.; Li, J. J. Org. Chem. 1997, 62, 4142.
52. Fukui, K.; Inamoto, Y.; Kitano, H.; Nagata, C. J. Org. Chem. 1961, 26, 1394.