ω-Functionalized 3-alkynylpyrazolo[1, 5-a]pyrimidines by sonogashira coupling

Synthesis

Volumn , Issue 1, 2005, Pages 131-135

  Yin, Lunxiang ^a   Liebscher, Jürgen ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Alkynes; Cross coupling; Heterocycles; Hydrogenation; Palladium

Indexed keywords

CARBON; CATALYSIS; CATALYSTS; HYDROGENATION; PALLADIUM;

HOMOPROPARGYLIC COMPOUNDS; PROPARGYLIC COMPOUNDS; SONOGASHIRA COUPLING;

SYNTHESIS (CHEMICAL);

3 (3 DIMETHYLAMINOPROPYL)PYRAZOLO[1,5 A]PYRIMIDINE; 3 IODOPYRAZOLO[1,5 A]PYRIMIDINE; HOMOPROPARGYL DERIVATIVE; PALLADIUM; PROPARGYL DERIVATIVE; PYRAZOLO[1,5 A]PYRIMIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CROSS COUPLING REACTION; HECK REACTION; HYDROGENATION; SONOGASHIRA REACTION;

EID: 12344304288     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-834923     Document Type: Article

References (54)

1. Novinson, T.; Bhooshan, B.; Okabe, T.; Revankar, G. R.; Wilson, H. R. J. Med. Chem. 1976, 19, 512.
2. Senga, K.; Novinson, T.; Wilson, H. R. J. Med. Chem. 1981, 24, 610.
3. Suzuki, M.; Iwasaki, H.; Fujikawa, Y.; Sakashita, M.; Kitahara, M.; Sakoda, R. Bioorg. Med. Chem. Lett. 2001, 11, 1285.
4. Almansa, C.; Arriba, A. F.; Cavalcanti, F. L.; Gomez, L. A.; Miralles, A.; Forn, J. J. Med. Chem. 2001, 44, 350.
5. Fraley, M. E.; Rubino, R. S.; Hoffman, W. P.; Hambaugh, S. R.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2002, 12, 3537.
6. Novinson, T.; Hanson, R.; Dimmitt, M. K.; Simmon, L. N.; Robins, R. K.; O'Brien, D. E. J. Med. Chem. 1974, 17, 645.
7. Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Costa, B.; Martini, C. Bioorg. Med. Chem. 2001, 9, 2661.
8. Kirkpatrick, W. E.; Okabe, T.; Hillyard, I. W.; Robin, R. K.; Dren, A. T. J. Med. Chem. 1977, 20, 386.
9. Calderwood, D. J.; Johnson, D. N.; Munschauer, R.; Rafferty, P. Bioorg. Med. Chem. Lett. 2002, 12, 1683.
10. Karanik, M.; Pätzel, M.; Liebscher, J. Synthesis 2003, 1201.
11. Yin, L. X.; Liebscher, J. Synthesis 2004, 2329.
12. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
13. (b) Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.
14. (c) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
15. (d) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
16. (e) Sakomoto, T.; Shiga, F.; Yasuhara, A.; Yamanaka, H. Synthesis 1992, 746.
17. (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: Oxford, 2000.
18. (b) Kalinin, V. N. Synthesis 1991, 413.
19. (c) Edo, K.; Yamanaka, H.; Sakamoto, T. Heterocycles 1978, 9, 271.
20. (d) Mcguigan, C.; Yarnold, C. J.; Jones, G.; Balzarini, J. J. Med. Chem. 1999, 42, 4479.
21. (e) Turner, S. C.; Esbenshade, T. A.; Bennani, Y. L.; Hancock, A. A. Bioorg. Med. Chem. Lett. 2003, 12, 1683.
22. (f) Arnautu, A.; Collot, V.; Ros, J. C.; Witulski, B. Tetrahedron Lett. 2002, 43, 2695.
23. (g) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697.
24. (h) Negishi, E.; Qian, M. X.; Zeng, F. X.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597.
25. (a) Muehldorf, A. V.; Guzman-Perez, A.; Kluge, A. F. Tetrahedron Lett. 1994, 35, 8755.
26. (b) Tilley, J. W.; Levitan, P.; Lind, J.; Welton, A. F.; O'Donnell, M. J. Med. Chem. 1987, 30, 185.
27. (c) Clitherow, J. W.; Scopes, D. C.; Skingle, M.; Jorden, C. C. J. Med. Chem. 1994, 37, 2253.
28. (d) Lammothe, M.; Pauwels, P. J.; Belliard, K.; Schambel, P.; Halazy, S. J. Med. Chem. 1997, 40, 3542.
29. (a) Elsevier, C. J.; Kleijn, H.; Ruitenberg, K.; Vermeer, P. J. Chem. Soc., Chem. Commun. 1983, 1529.
30. (b) Elsevier, C. J.; Kleijn, H.; Boersma, J.; Vermeer, P. Organometallics 1986, 5, 716.
31. Heidenreich, R. G.; Köhler, K.; Krauter, J. K.; Pietsch, J. Synlett 2002, 1118.
32. (a) Gala, D.; Jenkins, S. J.; Kugelman, M. Org. Proc. Res. Dev. 1997, 1, 163.
33. (b) Dyer, U. C.; Shapland, P. D.; Tiffin, P. D. Tetrahedron Lett. 2002, 42, 1765.
34. (c) McClure, M. S.; Roschangar, F.; Hodson, S. J.; Millar, A.; Osterhout, M. H. Synthesis 2001, 1681.
35. (d) Sakurai, H.; Tsukuda, T.; Hirao, T. J. Org. Chem. 2002, 67, 2721.
36. (e) Tagata, T.; Nishida, M. J. Org. Chem. 2003, 68, 9412.
37. (f) LeBlond, C. R.; Andrews, A. T.; Sun, Y. K.; Sowa, J. R. Jr. Org. Lett. 2001, 3, 1555.
38. (g) Organ, M. G.; Mayer, S. J. Comb. Chem. 2003, 5, 118.
39. (h) Accadi, A.; Cerichelli, G.; Chiarini, M.; Correa, M.; Zorzan, D. Eur. J. Org. Chem. 2003, 4080.
40. (a) Reardon, P.; Metts, S.; Crittendon, C.; Dangherity, P.; Parson, E. J. Organometallics 1995, 14, 3810.
41. (b) Hagiwara, H.; Shimizu, Y.; Hoshi, T.; Suzuki, T. Tetrahedron Lett. 2001, 42, 4349.
42. (c) Xie, X. P.; Lu, J. P.; Chen, B.; Han, J. J.; She, X. G.; Pan, X. F. Tetrahedron Lett. 2004, 45, 809.
43. (d) Mehnert, C. P.; Weaver, D. W.; Ying, J. Y. J. Am. Chem. Soc. 1998, 120, 12289.
44. (e) Khan, S. I.; Grinstaff, M. W. J. Org. Chem. 1999, 64, 1077.
45. (a) Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K, M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444.
46. (b) Bleicher, L. S.; Cosford, N. D. P. Synlett 1995, 1115.
47. (c) Cosford, N. D. P.; Bleicher, L.; Herbaut, A.; McCallum, J. S.; Vernier, J. M. J. Med. Chem. 1996, 39, 3235.
48. (d) Bleicher, L. S.; Cosford, N. D. P.; Herbaut, A.; McCallum, J. S.; McDonald, I. A. J. Org. Chem. 1998, 63, 1109.
49. (e) Novak, Z.; Szabo, A.; Kotschy, A. J. Org. Chem. 2003, 68, 3327.
50. (f) Bates, R. W.; Boonsombat, J. J. Chem. Soc., Perkin Trans, 1 2001, 654.
51. (g) Lopez-Deber, M. P.; Castedo, L.; Granja, J. R. Org. Lett. 2001, 3, 2823.
52. (h) Pal, M.; Subramanian, V.; Yeleswarapu, K. R. Tetrahedron Lett. 2003, 44, 8221.
53. Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571.
54. Fairlamb, I. J. S.; Bäuerlein, P. S.; Marrison, L. R.; Dickinson, J. M. Chem. Commun. 2003, 632.