Four-component synthesis of functionalized 2,2′-bipyridines based on the Blaise reaction

Synlett

Volumn , Issue 16, 2011, Pages 2311-2314

  Hommes, Paul ^a   Jungk, Phillip ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

ketoenamides; 2,2 bipyridines; condensation; multicomponent reaction; nonaflates; pyridines

Indexed keywords

2 PICOLYL CHLORIDE; 2,2' BIPYRIDINE DERIVATIVE; 4 HYDROXY 2,2' BIPYRIDINE DERIVATIVE; 4 HYDROXYPYRIDINE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; BLAISE REACTION; CATALYSIS; CHEMICAL REACTION; POLYMERIZATION;

EID: 80053097376     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1260304     Document Type: Article

References (42)

1. Blaise E E., C. R. Hebd. Seances Acad. Sci. 1901 132 478
2. Blaise E E., C. R. Hebd. Seances Acad. Sci. 1901 132 987
3. Blaise E E., Courtot A P., Bull. Soc. Chim. Fr. 1906 35 589
4. Benetti S, Romagnoli R, Chem. Rev. 1995 95 1065
5. Rao H S. P., Rafi S, Padmavathy K, Tetrahedron 2008 64 8037
6. Chun Y S., Lee K K., Ko Y O., Shin H, Lee S, Chem. Commun. 2008 5098
7. Ko Y O., Chun Y S., Park C.-L, Kim Y, Shin H, Ahn S, Hong J, Lee S, Org. Biomol. Chem. 2009 7 1132
8. Chun Y S., Ryu K Y., Ko Y O., Hong J Y., Hong J, Shin H, Lee S, J. Org. Chem. 2009 74 7556
9. Kim J H., Lee S, Org. Lett. 2011 13 1351
10. Review:, Lechel T, Reissig H.-U, Pure Appl. Chem. 2010 82 1835
11. Flögel O, Dash J, Brüdgam I, Hartl H, Reissig H.-U, Chem. Eur. J. 2004 10 4283
12. Dash J, Lechel T, Reissig H.-U, Org. Lett. 2007 9 5541
13. Lechel T, Dash J, Brüdgam I, Reissig H.-U, Eur. J. Org. Chem. 2008 3647
14. Eidamshaus C, Reissig H.-U, Adv. Synth. Catal. 2009 351 1162
15. Dash J, Reissig H.-U, Chem. Eur. J. 2009 15 6811
16. Lechel T, Brüdgam I, Reissig H.-U, Beilstein J. Org. Chem. 2010 6 No. 42
17. Lechel T, Dash J, Eidamshaus C, Brüdgam I, Lentz D, Reissig H.-U, Org. Biomol. Chem. 2010 8 3007
18. Lechel T, Dash J, Hommes P, Lentz D, Reissig H.-U, J. Org. Chem. 2010 75 726
19. Bera M K., Reissig H.-U, Synthesis 2010 2129
20. Eidamshaus C, Kumar R, Bera M K., Reissig H.-U, Beilstein J. Org. Chem. 2011 7 962
21. Eidamshaus, C.; Reissig, H.-U. Eur. J. Org. Chem. 2011, DOI: 10.1002/ejoc.201100681.
22. For a proposed mechanism, see ref. 5l.
23. Lehn J.-M, Supramolecular Chemistry - Concepts and Perspectives VCH Weinheim 1995
24. Kaes C, Katz A, Hosseini M W., Chem. Rev. 2000 100 3553
25. Schubert U S., Eschbaumer C, Angew. Chem. Int. Ed. 2002 41 2892; Angew. Chem. 2002, 114, 3016
26. Fletcher N C., J. Chem. Soc., Perkin Trans. 1 2002 1831
27. Ye B.-H, Tong M.-L, Chen X.-M, Coord. Chem. Rev. 2005 249 545
28. For reviews, see:, Kröhnke F, Synthesis 1976 1
29. Summers L A., The Bipyridines, In Advances in Heterocyclic Chemistry Vol. 35 Katritzky A R. Academic Press Orlando, FL 1984 281
30. Chelucci G, Thummel R P., Chem. Rev. 2002 102 3129
31. Varela J A., Saá C, Chem. Rev. 2003 103 3787
32. Newkome G R., Patri A K., Holder E, Schubert U S., Eur. J. Org. Chem. 2004 235
33. Hapke M, Brandt L, Lützen A, Chem. Soc. Rev. 2008 37 2782
34. Selected recent examples:, Altuna-Urquijo M, Gehre A, Stanforth S P., Tarbit B, Tetrahedron 2009 65 975
35. Gutz C, Lützen A, Synthesis 2010 85
36. Kremer C, Lützen A, Synthesis 2011 210
37. Duric S, Tzschucke C., Org. Lett. 2011 13 2310
38. Katritzky A R., He H.-Y, Suzuki K, J. Org. Chem. 2000 65 8210
39. Katritzky A R., Suzuki K, Wang Z, Synlett 2005 1656
40. Takaya H, Naota T, Murahashi S.-I, J. Am. Chem. Soc. 1998 120 4244
41. For a review on aryl and alkenyl nonaflates, see:, Högermeier J, Reissig H.-U, Adv. Synth. Catal. 2009 351 2747
42. Cacchi S, Ciattini P G., Morera E, Otar G, Tetrahedron Lett. 1986 27 5541