Synthesis of 2-substituted pyrimidines via cross-coupling reaction of pyrimidin-2-yl sulfonates with nucleophiles in polyethylene glycol 400

Synlett

Volumn , Issue 11, 2010, Pages 1657-1660

  Wang, Xi Cun ^a,b   Yang, Guo Jun ^a,b   Quan, Zheng Jun ^a,b   Ji, Peng Yan ^a,b   Liang, Jun Ling ^a,b   Ren, Rong Guo ^a,b  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

^b NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

2 substituted pyrimidines; cross coupling reaction; esterification; oxidation; PEG 400

Indexed keywords

CARBON; CHLOROFORM; DICHLOROMETHANE; MACROGOL 400; NITROGEN; NUCLEOPHILE; OXYGEN; PYRIDINE; PYRIMIDINE DERIVATIVE; SODIUM HYDROXIDE; SULFONIC ACID DERIVATIVE; SULFUR; TRIETHYLAMINE;

ARTICLE; BIGINELLI REACTION; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ESTERIFICATION; OXIDATION; REACTION TIME; ROOM TEMPERATURE; SYNTHESIS;

EID: 77953886429     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1258080     Document Type: Article

References (43)

1. Heldebrant D, Jessop P G., J. Am. Chem. Soc. 2003 125 5600
2. Hesis L, Gais H J., Tetrahedron Lett. 1995 36 3833
3. Haimov A, Neumann R, Chem. Commun. 2002 876
4. Wang X.-C, Quan Z.-J, Zhang Z, Tetrahedron 2007 63 8227
5. Chandrasekhar S, Narsihmulu Ch, Sultana S S., Reddy N R., Org. Lett. 2002 4 4399
6. Ackermann L, Vicente R, Org. Lett. 2009 11 4922
7. Zhou W.-J, Wang K.-H, Wang J.-X, J. Org. Chem. 2009 74 5599
8. Biginelli P, Gazz. Chim. Ital. 1893 23 360
9. Kappe C O., Tetrahedron 1993 49 6937
10. Kappe C O., Acc. Chem. Res. 2000 33 879
11. Kappe C O., Stadler A, Org. React. 2004 63 1
12. Dallinger D, Stadler A, Kappe C O., Pure Appl. Chem. 2004 76 1017
13. Gong L Z., Chen X H., Xu X Y., Chem. Eur. J. 2007 13 8920
14. Kolosov M A., Orlov V D., Mol. Diversity 2009 13 5
15. Quan Z.-J, Zhang Z, Da Y X, Wang X.-C, Chin. J. Org. Chem. 2009 29 876; in Chinese
16. Kappe C O., Eur. J. Med. Chem. 2000 35 1043
17. Deres K, Schroder C H., Paessens A, Goldmann S, Hacker H J., Weber O, Kraemer T, Niewoehner U, Pleiss U, Stoltefuss J, Graef E, Koletzki D, Masantschek R N. A., Reimann A, Jaeger R, Gro R, Beckermann B, Schlemmer K.-H, Haebich D, Rubsamen-Waigmann H, Science 2003 299 893
18. Lengar A, Kappe C O., Org. Lett. 2004 6 771
19. Sing K, Arora D, Poremsky E, Lowery J, Moreland R S., Eur. J. Med. Chem. 2009 44 1997
20. Singh K, Arora D, Singh K, Singh S, Mini Rev. Med. Chem. 2009 9 95
21. Snider B B., Shi Z, J. Org. Chem. 1993 58 3828
22. Patil A D., Kumar N V., Kokke W C., Bean M F., Freyer A J., DeBrosse C, Mai S, Truneh A, Gaulkner D J., Carte B, Breen A L., Hertzberg R P., Johnson R K., Westly J W., Potts B C., J. Org. Chem. 1995 60 1182
23. Aron Z D., Overman L E., Chem. Commun. 2004 253
24. The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals 13th ed. Merck Whitehouse Station 2001
25. Kappe C O., Roschger P, J. Heterocycl. Chem. 1989 26 55
26. Gholap A R., Toti K S., Shirazi F, Deshpande M V., Srinivasan K V., Tetrahedron 2008 64 10214
27. Watanabe M, Koike H, Ishiba T, Okada T, Seo S, Hirai K, Bioorg. Med. Chem. 1997 5 437
28. Kim D C., Lee Y R., Yang B.-S, Shin K J., Kim D J., Chung [nl]B Y., Yoo K H., Eur. J. Med. Chem. 2003 38 525
29. Kasparec J, Adams J L., Sisko J, Silva D J., Tetrahedron Lett. 2003 44 4567
30. Gayo L M., Suto [nl]M J., Tetrahedron Lett. 1997 38 211
31. Matloobi M, Kappe C O., J. Comb. Chem. 2007 9 275
32. Obrecht D, Abrecht C, Grieder A, Villalgordo J M., Helv. Chim. Acta 1997 80 65
33. VandenEynde J J., Labuche N, VanHaverbeke Y, Tietze L, ARKIVOC 2003 (xv) 22
34. VandenEynde J J., Audiart N, Canonne V, Michel S, VanHaverbeke Y, Kappe C O., Heterocycles 1997 45 1967
35. Yamamoto K, Chen Y G., Buono F G., Org. Lett. 2005 7 4673
36. Kang F A., Kodah J, Guan Q Y., Li X B., Murray [nl]W V., J. Org. Chem. 2005 70 1957
37. Matsushima A, Oda M, Kawachi Y, Chika J, WO 03/006439 A1 2003
38. Rueter J K., Nortey S O., Baxter E W., Leo G C., Reitz A B., Tetrahedron Lett. 1998 39 975
39. Zhang M J., Moore J D., Flynn D L., Hanson P R., Org. Lett. 2004 6 2657
40. Cho C.-L, Yun H.-S, Park K, J. Org. Chem. 2003 68 3017
41. Choi J H., Lee B C., Lee H W., Lee I, J. Org. Chem. 2002 67 1277
42. Gao C.-Y, Yang [nl]L.-M, J. Org. Chem. 2008 73 1624
43. Bza T, Krl V, Martsek P, Kaplnek R, J. Fluorine Chem. 2008 129 235