Facile synthesis of fluorinated 1-desazapurines

Synthesis

Volumn , Issue 11, 2009, Pages 1865-1875

  Iaroshenko, Viktor O ^a,b   Sevenard, Dmitri V ^c   Volochnyuk, Dmitriy M ^a,d   Wang, Yan ^e   Martiloga, Alexander ^b   Tolmachev, Andrei O ^a,b  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b ENAMINE LTD   (Ukraine)

^c UNIVERSITY OF BREMEN   (Germany)

^d INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

^e UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Annulations; Diketones; Fluorine; Imidazoles; Pyridines; Regioselectivity

Indexed keywords

ANNULATIONS; DIKETONES; FACILE SYNTHESIS; IMIDAZOLES; SYNTHETIC ROUTES;

KETONES; PYRIDINE; REGIOSELECTIVITY; SUGAR (SUCROSE); SUGARS; SYNTHESIS (CHEMICAL);

FLUORINE;

1 DEAZAPURINE DERIVATIVE; DIKETONE; ELECTROPHILE; FLUORINE; HETEROCYCLIC COMPOUND; IMIDAZO[4,5 B]PYRIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CURTIUS REARRANGEMENT; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINATION; REACTION ANALYSIS;

EID: 67650047679     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216802     Document Type: Article

References (62)

1. (a) Dubey, P. K.; Kumar, R. V.; Naidu, A.; Kulkarni, S. M. A. Asian J. Chem. 2002, 14, 1129.
2. (b) Lee, S. Ch.; Choi, J. S.; Oh, J. H.; Park, B.; Kim, Y. E.; Lee, J. H.; Shin, D.; Kim, Ch. M.; Hyun, Y.-L.; Lee, C. h. S.; Cho, J.-M.; Ro, S. WO 83978 2007; Chem. Abstr. 2007, 147, 817587.
3. (c) Kelly, M. G.; Kincaid, J.; Duncton, M.; Sahasrabudhe, K.; Janagani, S.; Upasani, R. B.; Wu, G.; Fang, Y.; Wei, Zh.-L. US 194801 2006; Chem. Abstr. 2006, 145, 889269.
4. (d) Randolph, J. T.; Chen, H.; Degoey, D. A.; Flentge, Ch. A.; Flosi, W. J.; Grampovnik, D. J.; Huang, P. P.; Hutchinson, D. K.; Kempf, D. J.; Klein, L. L.; Yeung, M. C. US 159469 2005; Chem. Abstr. 2005, 143, 641882.
5. (e) Kivlighn, S. D.; Zingaro, G. J.; Gabel, R. A.; Broten, T. P.; Schorn, T. W.; Schaffer, L. W.; Naylor, E. M.; Chakravarty, P. K.; Patchett, A. A.; Greenlee, W. J.; Siegl, P. K. S. Am. J. Hypertens. 1995, 8, 58.
6. (a) Pagani, E. D.; Dundore, R. L.; Bode, D. C.; Bacon, E. R.; Singh, B.; Lesher, G. Y.; Buchholz, R. A.; Silver, P. J. J. Cardiovasc. Pharmacol. 1994, 24, 403.
7. (b) Joseph, E. C.; Rees, J. A.; Dayan, A. Toxicol. Pathol. 1996, 24, 436.
8. (c) Garvey, D. S.; Saenz de Tejada, I.; Earl, R. A.; Khanapure, S. P. US 6331543, 2001; Chem. Abstr. 2001, 136, 916407.
9. (a) Ida, K.; Otsubo, N.; Kuboyama, T.; Arai, H.; Watanabe, A.; Saki, M.; Hiura, N.; Manabe, H.; Takada, H.; Saito, J. WO 82905, 2005; Chem. Abstr. 2005, 143, 979654.
10. (b) Magnuson, S.; Dixon, J.; Phillips, B.; Khire, U.; Wang, L.; Zhang, Z.; Patel, M.; Kumarasinghe, E. S.; Wickens, P.; Oblague, A. WO 64932, 2007; Chem. Abstr. 2007, 147, 618350.
11. (c) Bavetsias, V.; Sun, C.; Bouloc, N.; Reynisson, J.; Workman, P.; Linardopoulos, S.; McDonald, E. Bioorg. Med. Chem. Lett. 2007, 17, 6567.
12. (a) Hackova, D.; Hocek, M.; Dvorakova, H.; Votruba, I. Tetrahedron 1999, 55, 11109.
13. (b) Koch, M.; Den, H.; Jacobus, A.; Koomen, J.; Wanner, G.-J.; Martinus, J.; Roelof, F. W. WO 27365, 2006.
14. (c) Erion, M. D. M.; Reddy, R. J. Am. Chem. Soc. 1998, 120, 3295.
15. (d) Veliz, E. A.; Stephens, O. M.; Beal, P. A. Org. Lett. 2001, 3, 2969.
16. For 'de novo' synthesis, see, for example: (a) Rolfes, R. J. Biochem. Soc. Trans. 2006, 34, 786.
17. (b) Christopherson, R. J.; Lyons, S. D.; Wilson, P. K. Acc. Chem. Res. 2002, 35, 961.
18. (c) Zalkin, H.; Dixon, J. E. Prog. Nucleic Acid Res. Mol. Biol. 1992, 42, 259.
19. For 'salvage' synthesis, see, for example: (a) Manfredi, J. P.; Holmes, E. W. Annu. Rev. Physiol. 1985, 47, 691.
20. (b) Berens, R. L.; Krug, E. C.; Marr, J. J. Biochem. Mol. Biol. Parasites 1995, 89.
21. (a) Lawhorn, B. G.; Mehl, R. A.; Begley, T. P. Org. Biomol. Chem. 2004, 2, 2538; and references cited therein.
22. (b) Humpfries, M. J.; Ramsden, C. A. Synlett 1995, 203.
23. (c) Vyskocilova, P.; Hornik, P.; Friedecky, D.; Frycak, P.; Lemr, K.; Adam, T. Nucleosides, Nucleotides Nucleic Acids 2006, 25, 9.
24. (a) Al-Shaar, A. H.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, Ch. J. Chem. Soc., Chem. Commun. 1989, 551.
25. (b) Clayton, R.; Davis, M. L.; Fraser, W.; Li, W.; Ramsden, Ch. A. Synlett 2002, 1483.
26. (c) Wang, Z.; Huynh, H. K.; Han, B.; Krishnamurthy, R.; Eschenmoser, A. Org. Lett. 2003, 5, 2067.
27. (d) Al-Shaar, A. H. M.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, Ch. A. J. Chem. Soc., Perkin Trans. 1 1992, 2779.
28. (e) Al-Shaar Adnan, H. M.; Chambers, R. K.; Gilmour, D. W.; Lythgoe, D. J.; McClenaghan, I.; Ramsden, Ch. A. J. Chem. Soc., Perkin Trans. 1 1992, 2789.
29. (f) Iaroshenko, V. O.; Volochnyuk, D. M.; Wang, Y.; Vovk, M. V.; Boiko, V. J.; Rusanov, E. B.; Groth, U. M.; Tolmachev, A. O. Synthesis 2007, 3309.
30. (a) Iaroshenko, V. O.; Volochnyuk, D. M.; Wang, Y.; Vovk, M. V.; Boiko, V. J.; Rusanov, E. B.; Groth, U. M.; Tolmachev, A. O. Synthesis 2007, 3309.
31. (b) Iaroshenko, V. O.; Groth, U.; Kryvokhyzha, N. V.; Obeid, S.; Tolmachev, A. A.; Wesch, T. Synlett 2008, 343.
32. (c) Volochnyuk, D. M.; Pushechnikov, A. O.; Krotko, D. G.; Sibgatulin, D. A.; Kovalyova, S. A.; Tolmachev, A. A. Synthesis 2003, 1531.
33. (d) Vovk, M. V.; Bolbut, A. V.; Boiko, V. I.; Pirozhenko, V. V.; Chernega, A. N.; Tolmachev, A. A. Chem. Heterocycl. Compd. (N. Y., NY, U. S.) 2004, 40, 370.
34. (e) Vovk, M. V.; Bol'but, A. V.; Dorokhov, V. I.; Pyrozhenko, V. V. Synth. Commun. 2002, 32, 3749.
35. (f) Iaroshenko, V. O.; Volochnyuk, D. M.; Kryvokhyzha, N. V.; Martyloga, A.; Sevenard, D. V.; Groth, U.; Brand, J.; Chernega, A. N.; Shivanyuk, A. N.; Tolmachev, A. A. Synthesis 2008, 2337.
36. (g) Iaroshenko, V. O.; Sevenard, D. V.; Kotljarov, A. V.; Volochnyuk, D. M.; Tolmachev, A. O.; Sosnovskikh, V. Ya. Synthesis 2009, 731.
37. (a) Lythgoe, D. J.; Ramsden, C. A. Adv. Heterocycl. Chem. 1994, 61, 1.
38. (b) Groziak, M. P.; Ding, H. Acta Chim. Slov. 2000, 47, 1.
39. (a) Kinoshita, T.; Watanabe, H.; Sato, S.; Tamura, C. Bull. Chem. Soc. Jpn. 1980, 53, 442.
40. (b) Hosmane, R. S.; Burnett, F. N.; Albert, M. S. J. Org. Chem. 1984, 49, 1212.
41. (c) Naylor, R. N.; Shaw, G.; Wilson, D. V.; Butler, D. N. J. Chem. Soc. 1961, 4845.
42. Lissel, M. Liebigs Ann. Chem. 1987, 77.
43. D'Aurio, M.; D'Onofrio, F.; Suwinski, J.; Swierczek, K. Tetrahedron 1993, 49, 3899.
44. (a) Beauchamp, L. M.; Serling, B. L.; Kelsey, J. E.; Biron, K. K.; Collins, P.; Selway, J.; Lin, J. C.; Schaeffer, H. J. J. Med. Chem. 1988, 31, 144.
45. (b) Kumar, R.; Semaine, W.; Johar, M.; Tyrrell, D. L. J.; Agrawal, B. J. Med. Chem. 2006, 49, 3693.
46. Yang, M.; Ye, W.; Schneller, S. W. J. Org. Chem. 2004, 69, 3993.
47. Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373.
48. Ichiro, H.; Tsuneo, M.; Michiko, K.; Shigeyuki, Y. J. Am. Chem. Soc. 2007, 129, 15549.
49. (a) Luscombe, C.; Pedersen, J.; Uren, E.; Locarnini, S. J. Hepatol. 1996, 24, 766.
50. (b) Kruining, J.; Heijtink, R. A.; Schalm, S. W. J. Hepatol. 1995, 22, 263.
51. (a) Husaka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1967, 21, 255.
52. (b) Kishi, T.; Muroi, M.; Kusaka, T.; Nishikawa, M.; Kamiya, K.; Mizuno, K. Chem. Pharm. Bull. 1972, 20, 940.
53. (c) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
54. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
55. (a) Reid, J. C.; Calvin, M. J. Am. Chem. Soc. 1950, 72, 2948.
56. (b) Park, J. D.; Brown, H. A.; Lacher, J. R. J. Am. Chem. Soc. 1953, 75, 4753.
57. (c) Pashkevich, K. I.; Khomutov, O. G.; Sevenard, D. V. Russ. J. Org. Chem. 1998, 34, 1727;
58. Zh. Org. Khim. 1998, 34, 1798.
59. (d) Sevenard, D. V.; Lork, E. J. Fluorine Chem. 2004, 125, 125.
60. (e) Sevenard, D. V.; Sosnovskikh, V. Ya.; Iaroshenko, V. O. unpublished results.
61. (a) Malliet, P.; Le Brun, A.; Thompson, F.; Tiraboschi, G. WO 108685, 2004.
62. (b) Decreau, R. A.; Collman, J. P.; Yang, Y.; Yan, Y.; Devarai, N. K. J. Org. Chem. 2007, 72, 2794.