Copper(II)-catalyzed synthesis of pyrimidines from propargylic alcohols and amidine: A propargylation-cyclization-oxidation tandem reaction

Synlett

Volumn , Issue 8, 2011, Pages 1179-1183

  Lin, Min ^a   Chen, Qing Zhen ^a   Zhu, Yu ^a   Chen, Xin Liang ^a   Cai, Ji Jun ^a   Pan, Ying Ming ^a   Zhan, Zhuang Ping ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

amidine; annulation; copper; propargylation; pyrimidine

Indexed keywords

1,2 DICHLOROETHANE; ACETONITRILE; ALCOHOL; AMIDINE; CHLOROBENZENE; COPPER; DICHLOROMETHANE; NITROMETHANE; PROPARGYLIC ALCOHOL; PYRIMIDINE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; OXIDATION; PROPARGYLATION; SOLVENT EFFECT; SUBSTITUTION REACTION; SYNTHESIS;

EID: 79955662647     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259954     Document Type: Article

References (46)

1. For representative examples of the application of pyrimidines, see:, Lin Y.-L, Huang R.-L, Chang [nl]C.-M, Kuo Y.-H, J. Nat. Prod. 1997 60 982
2. Gerlinck R G. S., Braekman J C., Daloze D, Bruno I, Riccio R, Rogeau D, Amade P, J. Nat. Prod. 1992 55 528
3. Traxler P, Bold G, Buchdunger E, Caravatti G, Furet P, Manley P, OReilly T, Wood J, Zimmermann J, Med. Res. Rev. 2001 21 499
4. Zimmermann J, Buchdunger E, Mett H, Meyer T, Lydon N B., Bioorg. Med. Chem. Lett. 1997 7 187
5. Hend N H., Hebat-Allah S A., Abdel-Rahman B A., Acta Pharm. 2008 58 359
6. Dupin J P., Gryglewski R J., Gravier D, Hou G, Casadebaig F, Swies J, Chlopicki S, J. Physiol. Pharmacol. 2002 53 625
7. Nada M A., Hamdi M H., Nadia G K., Omar A M., Molecules 2008 13 1501
8. For representative examples, see:, Vicario J, Aparicio D, Palacios F, J. Org. Chem. 2009 74 452
9. Robin A, Julienne K, Meslin J C., Deniaud D, Eur. J. Org. Chem. 2006 634
10. Sakai N, Aoki Y, Sasada T, Konakahara T, Org. Lett. 2005 7 4705
11. Guzmn A, Romero M, Talams F X., J. Org. Chem. 1996 61 2470
12. Martinez A G., Fernndez A H., Alvarez R M., Vilchez M D. M., Gutierrez M L. L., Subramanian L R., Tetrahedron 1999 55 4825
13. Krechl J, Perez M A., Cuadrado F J., Soto J L., Synthesis 1988 122
14. Ghosez L, Jnoff E, Bayard P, Sainte F, Beaudegnies R, Tetrahedron 1999 55 3387
15. Movassaghi M, Hill M D., J. Am. Chem. Soc. 2006 128 14254
16. Baxendale I R., Ley S V., J. Comb. Chem. 2005 7 483
17. Kakiya H, Yagi K, Shinokubo H, Oshima K, J. Am. Chem. Soc. 2002 124 9032
18. Blangetti M, Deagostino A, Prandi C, Zavattaro C, Venturello P, Chem. Commun. 2008 1689
19. For reviews, see:, Joule J A., Mills K, In Heterocyclic Chemistry 4th ed. Blackwell Science London 2000 194-215
20. BansalRaj K, In Heterocyclic Chemistry 4th ed. New Age New Delhi 2007 514-560
21. Rewcastle G W., In Comprehensive Heterocyclic Chemistry III Vol. 8 Katritzky A R. Aitken R A. Elsevier Oxford 2008 Chap. 8.02 191-203
22. Rewcastle G W., In Comprehensive Heterocyclic Chemistry III Vol. 8 Katritzky A R. Aitken R A. Elsevier Oxford 2008 Chap. 8.02 235-245
23. Hill M D., Movassaghi M, Chem. Eur. J. 2008 14 6836
24. Simon C, Constantieux T, Rodriguez J, Eur. J. Org. Chem. 2004 4957
25. For selected examples, see:, Palanki M S., Erdman [nl]P E., Gayo-Fung L M., Shevlin G I., Sullivan R W., Goldman M E., Ransone L J., Bennett B L., Manning [nl]A M., Suto M J., J. Med. Chem. 2000 43 3995
26. Kiselyov A S., Tetrahedron Lett. 2005 46 1663
27. Bagley M C., Brace C, Dale J W., Ohnesorge M, Phillips N G., Xiong X, Bower J, J. Chem. Soc., Perkin Trans. 1. 2002 1663
28. Rossi E, Abbiati G, Pini E, Synlett 1999 1265
29. Mller T J. J., Braun R, Ansorge M, Org. Lett. 2000 2 1967
30. Bagley M C., Hughes D D., Lubinu M C., Merritt E A., Taylor P H., Tomkinson N C., QSAR Comb. Sci. 2004 23 859
31. Bagley M C., Hughes D D., Taylor P H., Synlett 2003 259
32. Bannwarth P, Valleix A, Gre D, Gre R, J. Org. Chem. 2009 74 4646
33. Adamo M F. A., Adlington R M., Baldwin J E., Pritchard G J., Rathmell R E., Tetrahedron 2003 59 2197
34. Baldwin J E., Pritchard G J., Rathmell R E., [nl]J. Chem. Soc., Perkin Trans. 1 2001 2906
35. Adlington R M., Baldwin J E., Catterick D, Pritchard G, J. Chem. Soc., Perkin Trans. 1 1999 855
36. Karpov A S., Mller T J. J., Synthesis 2003 2815
37. Karpov A S., Mller T J. J., Org. Lett. 2003 5 3451
38. Bagley M C., Hughes D D., Sabo H M., Taylor P H., Xiong X, Synlett 2003 1443
39. Bagley M C., Lin Z, Pope S J. A., Tetrahedron Lett. 2009 50 6818
40. Taylor R J. K., Reid M, Foot J, Raw S A., Acc. Chem. Res. 2005 38 851
41. Hao L, Pan Y, Wang T, Lin M, Chen L, Zhan Z, Adv. Synth. Catal. 2010 352 3215
42. Wang T, Ma R, Liu L, Zhan Z, Green Chem. 2010 12 1576
43. Pan Y, Zheng F, Lin H, Zhan Z, J. Org. Chem. 2009 74 3148
44. Liu X, Huang L, Zheng F, Zhan Z, Adv. Synth. Catal. 2008 350 2778
45. Zhan Z, Cai X, Wang S, Yu J, Liu H, Cui Y, J. Org. Chem. 2007 72 9838
46. Zhan Z, Yu J, Liu H, Cui Y, Yang R, Yang W, Li J, J. Org. Chem. 2006 71 8298