Synthesis and Suzuki-Miyaura reactions of 5-halo-3,4-dihydropyrimidin-2(1H) -ones

Tetrahedron Letters

Volumn 51, Issue 39, 2010, Pages 5103-5105

  Zych, Andrew J ^a   Wang, Hong Jun ^a   Sakwa, Samuel A ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 HALO 3,4 DIHYDROPYRIMIDIN 2 (1H) ONE DERIVATIVE; BORONIC ACID DERIVATIVE; HALIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIGINELLI REACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DECARBOXYLATION; HALODECARBOXYLATION; MIYAURA REACTION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 77956226146     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.093     Document Type: Article

References (24)

1. Review: C.O. Kappe Acc. Chem. Res. 33 2000 879
2. C.O. Kappe, and A. Stadler Org. React. 63 2004 1
3. F.L. Zumpe, M. Flüß, K. Schmitz, and A. Lender Tetrahedron Lett. 48 2007 1421
4. I. Suzuki, Y. Iwata, and K. Takeda Tetrahedron Lett. 49 2008 3238
5. R.J. Schmidt, L.J. Lombardo, S.C. Traeger, and D.K. Williams Tetrahedron Lett. 49 2008 3009
6. C.O. Kappe, H. Prokopcová, and L. Pisani Synlett 2007 43
7. A. Lengar, and C.O. Kappe Org. Lett. 6 2004 771
8. K. Singh, D. Arora, and S. Singh Tetrahedron Lett. 48 2007 1349
9. D. Gong, L. Zhang, and C. Yuan Heteroat. Chem. 14 2003 13
10. Z. Hassani, M.R. Islami, and M. Kalantari Bioorg. Med. Chem. Lett. 16 2006 4479
11. T.G. Steele, C.A. Coburn, M.A. Patane, and M.G. Bock Tetrahedron Lett. 39 1998 9315
12. D.S. Bose, L. Fatima, and H.B. Mereyala J. Org. Chem. 68 2003 587
13. I. Cepanec, M. Litvić, M. Filipan-Litvić, and I. Grüngold Tetrahedron 63 2007 11822
14. A. Shaabani, A. Bazgir, and F. Teimouri Tetrahedron Lett. 44 2003 857
15. 6) δ 9.26 (s, 1H), 7.79 (s, 1H), 7.40-7.10 (m, 10H), 5.19-5.03 (m, 3H), 2.30 (s, 3H).
16. C.O. Kappe Tetrahedron 32 1993 6938
17. 6) δ 11.92 (s, 1H), 9.07 (s, 1H), 7.68 (s, 1H), 7.40-7.20 (m, 5H), 5.12 (s, 1H), 2.27 (s, 3H).
18. K.J. Lee, K.W. Lim, and D.Y. Chi Bull. Korean Chem. Soc. 22 2001 549
19. +. Synthesis of 3a: same as the above procedure with sodium bromide in place of sodium iodide. Note: some bromination of 6-methyl position was observed when greater equivalents of Oxone® were used.
20. Reference for bromination of DMPM 6-methyl position: B. Khanetskyy, D. Dallinger, and C.O. Oliver Kappe J. Comb. Chem. 6 2004 884
21. P. Beswick, S. Bingham, C. Bountra, T. Brown, K. Browning, I. Campbell, I. Chessell, N. Clayton, S. Collins, J. Corfield, S. Guntrip, C. Haslam, P. Lambeth, F. Lucas, N. Mathews, G. Murkit, A. Naylor, N. Pegg, E. Pickup, H. Player, H. Price, A. Stevens, S. Stratton, and J. Wiseman Bioorg. Med. Chem. Lett. 14 2004 5445
22. T. Kato, M. Tejima, H. Ebiike, and K. Achiwa Chem. Pharm. Bull. 44 1996 1132
23. V.N. Telvekar, N.D. Arote, and O.P. Herlekar Synlett 16 2005 2495
24. +.