Palladium-catalyzed oxidative C-H/C-H cross-couplings of thiazolo[5,4-d]pyrimidine with aromatic (hetero)cycles

Tetrahedron

Volumn 70, Issue 23, 2014, Pages 3730-3734

  Yang, Sheng Wei ^a   Su, Ye Xiang ^a   Sun, Li Ping ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

C H activation; Cross coupling; Palladium catalyzed; Thiazolo 5,4 d pyrimidine

Indexed keywords

4 (5 METHYL 2 (1 METHYL 1H PYRROL 2 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 (5 METHYL 2 PHENYLTHIAZOLO[5,4 D]PYRIMIDIN 7 YL)MORPHOLINE; 4 [2 (1,2 DIMETHYL 1H IMIDAZOL 5 YL) 5 METHYLTHIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [2 (2,5 DIMETHYLPHENYL) 5 METHYLTHIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [2 (4 METHOXYPHENYL) 5 METHYLTHIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [2 (5 CHLOROTHIOPHEN 2 YL) 5 METHYLTHIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [2 (BENZO[D]THIAZOL 2 YL) 5 METHYLTHIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [5 METHYL 2 (1 METHYL 1H IMIDAZOL 5 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [5 METHYL 2 (1 METHYL 1H PYRROL 2 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [5 METHYL 2 (2 METHYLTHIAZOL 5 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [5 METHYL 2 (3 METHYLTHIOPHEN 2 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [5 METHYL 2 (4 METHYLTHIOPHEN 2 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; 4 [5 METHYL 2 (THIOPHEN 2 YL)THIAZOLO[5,4 D]PYRIMIDIN 7 YL]MORPHOLINE; PALLADIUM; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; ARYLATION; CATALYST; CROSS COUPLING REACTION; CYCLIZATION; HYDROGEN BOND; OXIDATIVE COUPLING; PRIORITY JOURNAL;

EID: 84899934405     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.03.103     Document Type: Article

References (44)

1. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1470
2. 2nd ed. A. de Meijere, and F. Diederich Metal-Catalyzed Cross-Coupling Reactions Vol. 1-2 2004 Wiley-VCH Weinheim, Germany
3. J.P. Corbet, and G. Mignani Chem. Rev. 106 2006 2651 2710
4. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
5. L. Ackermann Chem. Commun. (Camb) 2010 4866 4877
6. L. Basolo, E.M. Beccalli, E. Borsini, and G. Broggini Tetrahedron 65 2009 3486 3491
7. B. Liegault, D. Lee, M.P. Huestis, D.R. Stuart, and K. Fagnou J. Org. Chem. 73 2008 5022 5028
8. L. Ackermann, R. Vicente, and A.R. Kapdi Angew. Chem., Int. Ed. 48 2009 9792 9826
9. X. Chen, K.M. Engle, D.H. Wang, and J.Q. Yu Angew. Chem., Int. Ed. 48 2009 5094 5115
10. J. Yamaguchi, A.D. Yamaguchi, and K. Itami Angew. Chem., Int. Ed. 51 2012 8960 9009
11. C.S. Yeung, and V.M. Dong Chem. Rev. 111 2011 1215 1292
12. T. de Haro, and C. Nevado J. Am. Chem. Soc. 132 2010 1512 1513
13. D. Mandal, A.D. Yamaguchi, J. Yamaguchi, and K. Itami J. Am. Chem. Soc. 133 2011 19660 19663
14. G. Meng, H.Y. Niu, G.R. Qu, J.S. Fossey, J.P. Li, and H.M. Guo Chem. Commun. (Camb) 48 2012 9601 9603
15. S. Potavathri, K.C. Pereira, S.I. Gorelsky, A. Pike, A.P. LeBris, and B. DeBoef J. Am. Chem. Soc. 132 2010 14676 14681
16. D.R. Stuart, E. Villemure, and K. Fagnou J. Am. Chem. Soc. 129 2007 12072 12073
17. D.R. Stuart, and K. Fagnou Science 316 2007 1172 1175
18. K.L. Hull, E.L. Lanni, and M.S. Sanford J. Am. Chem. Soc. 128 2006 14047 14049
19. B.S. Lane, M.A. Brown, and D. Sames J. Am. Chem. Soc. 127 2005 8050 8057
20. T.A. Dwight, N.R. Rue, D. Charyk, R. Josselyn, and B. DeBoef Org. Lett. 9 2007 3137 3139
21. W. Han, P. Mayer, and A.R. Ofial Angew. Chem., Int. Ed. 50 2011 2178 2182
22. G. Wu, J. Zhou, M. Zhang, P. Hu, and W. Su Chem. Commun. (Camb) 48 2012 8964 8966
23. C.C. Malakar, D. Schmidt, J. Conrad, and U. Beifuss Org. Lett. 13 2011 1378 1381
24. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, and J. You J. Am. Chem. Soc. 132 2010 1822 1824
25. F. Gosselin, S.J. Savage, N. Blaquiere, and S.T. Staben Org. Lett. 14 2012 862 865
26. G. Brasche, J. Garcia-Fortanet, and S.L. Buchwald Org. Lett. 10 2008 2207 2210
27. C.Y. He, S. Fan, and X. Zhang J. Am. Chem. Soc. 132 2010 12850 12852
28. R.W. Luke, P. Ballard, D. Buttar, L. Campbell, J. Curwen, S.C. Emery, A.M. Griffen, L. Hassall, B.R. Hayter, C.D. Jones, W. McCoull, M. Mellor, M.L. Swain, and J.A. Tucker Bioorg. Med. Chem. Lett. 19 2009 6670 6674
29. F. Giordanetto, B. Kull, and A. Dellsen Bioorg. Med. Chem. Lett. 21 2011 829 835
30. M.Y. Jang, Y. Lin, S. De Jonghe, L.J. Gao, B. Vanderhoydonck, M. Froeyen, J. Rozenski, J. Herman, T. Louat, K. Van Belle, M. Waer, and P. Herdewijn J. Med. Chem. 54 2011 655 668
31. R.C. Young, M. Jones, K.J. Milliner, K.K. Rana, and J.G. Ward J. Med. Chem. 33 1990 2073 2080
32. S.J. Childress, and R.L. Mckee J. Am. Chem. Soc. 73 1951 3862 3864
33. E. Chinoporos, S.C.J. Fu, and H. Terzian J. Org. Chem. 30 1965 1916 1920
34. G.H. Hitchings, and E.A. Falco J. Am. Chem. Soc. 72 1950 3203 3205
35. D.T. Hurst, S. Atcha, and K.L. Marshall Aust. J. Chem. 44 1991 129 134
36. Q.F. Zhong, and L.P. Sun Tetrahedron 66 2010 5107 5111
37. D. Xu, L.P. Sun, and Q.D. You Tetrahedron 68 2012 4248 4251
38. Y.X. Su, Y.H. Deng, T.T. Ma, Y.Y. Li, and L.P. Sun Green. Chem. 14 2012 1979 1981
39. X. Gong, G. Song, H. Zhang, and X. Li Org. Lett. 13 2011 1766 1799
40. K. Shen, Y. Fu, J.N. Li, L. Liu, and Q.X. Guo Tetrahedron 63 2007 1568 1576
41. K. Kikukawa, T. Yamane, M. Tkagi, and T. Matsuda J. Chem. Soc., Chem. Commun. 1972 695 696
42. T. Yamano, K. Kikukawa, T. Takagi, and M. Matsuda Tetrahedron 29 1973 955 962
43. A.D. Ryabov, and A.K.J. Yatsimirsky Mol. Catal. 4 1978 449 452
44. Z.Y. Li, H.P. Zhou, J.Y. Xu, X.M. Wu, and H.Q. Yao Tetrahedron 69 2013 3281 3286