A route to alkenyl-substituted 4-hydroxypyridine and pyrimidine derivatives via three-component access to β-alkoxy β-ketoenamides

Synthesis

Volumn , Issue 13, 2010, Pages 2129-2138

  Bera, Mrinal K ^a   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

alkoxyallenes; enamides; nonaflates; pyridines; pyrimidines; Suzuki couplings

Indexed keywords

ALKENYL; ALKENYL GROUPS; ALKOXYALLENES; AMMONIUM SALT; CATALYZED COUPLING; ENAMIDES; HETEROCYCLES; HYDROXYPYRIDINE; METHYL GROUP; PYRIMIDINE DERIVATIVES; SUZUKI COUPLINGS; THREE COMPONENT REACTIONS; THREE-COMPONENT; TRIFLATES; TRIMETHYLSILYL; UNSATURATED CARBOXYLIC ACIDS;

AMMONIUM COMPOUNDS; CARBOXYLIC ACIDS; COUPLINGS; CYANIDES; FUNCTIONAL GROUPS; HYDROCARBONS; ORGANIC ACIDS; PALLADIUM; PYRIDINE;

AROMATIC COMPOUNDS;

4 HYDROXYPYRIDINE; 6 ALKENYL 4 HYDROXYPYRIDINE DERIVATIVE; ALKENYL GROUP; ALLENE DERIVATIVE; ALPHA,BETA UNSATURATED CARBOXYLIC ACID DERIVATIVE; AMIDE; AMMONIA; BETA ALKOXY BETA KETOENAMIDE; CARBOXYLIC ACID DERIVATIVE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; METHOXYALLENE; NITRILE; PALLADIUM; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ORGANIC CHEMISTRY;

EID: 77953855754     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218787     Document Type: Article

References (78)

1. Coutts R T., Casy F A., Chem. Heterocycl. Compd. (Engl. Transl.) 1975 14 445
2. McInnes A G., Smith D G., Wright J L. C., Vining L C., Can. J. Chem. 1977 55 4159
3. Berthel S J., Marks I M., Yin X, Mischke S G., Orzechowski L, Pezzoni G, Sala F, Vassilev L T., Anti-Cancer Drugs 2002 13 359
4. Bringmann G, Reichert Y, Kane V, Tetrahedron 2004 60 3539
5. Chinchilla R, Nájera C, Yus M, Chem. Rev. 2004 104 2667
6. Schnermann M J., Boger D L., J. Am. Chem. Soc. 2005 127 15704
7. Whitson E L., Mala S M. V. D., Veltri C A., Bugni T S., deSilva E D., Ireland C M., J. Nat. Prod. 2006 69 1833
8. Horiuch M, Murakami C, Fukamiya N, Yu D, Chen T.-S, Bastow K F., Zhang D.-C, Taishi Y, Imakura Y, Lee K.-H, J. Nat. Prod. 2006 69 1271
9. Kariya Y, Kubota T, Fromont J, Kobayashi J, Tetrahedron Lett. 2006 47 997
10. Nishi T, Kubota T, Fromont J, Sasaki T, Kobayashi J, Tetrahedron 2008 64 3127
11. Aida W, Ohtsuki T, Li X, Ishibashi M, Tetrahedron 2009 65 369
12. Hayashi A, Arai M, Fujita M, Kobayashi M, Biol. Pharm. Bull. 2009 32 1261
13. Functional Organic Materials Müller T J. J. Bunz U H. F. ed Wiley-VCH Weinheim 2007
14. Hofmeier H, Schubert U S., Chem. Commun. 2005 2423
15. Schubert U S., Eschbaumer C, Angew. Chem. Int. Ed. 2002 41 2892
16. Angew. Chem. 2002, 114, 3016
17. Lehn J.-M, Supramolecular Chemistry-Concepts and Perspective Wiley-VCH Weinheim 1995
18. Karpov A S., Müller T J. J., Synthesis 2003 2815
19. Bevk D, Groselj U, Meden A, Svete J, Stanovnik B, Helv. Chim. Acta 2007 90 1737
20. Sagar R, Kim M.-J, Park S B., Tetrahedron Lett. 2008 49 5080
21. Xie F, Zhao H, Zhao L, Lou L, Hu L, Bioorg. Med. Chem. Lett. 2009 19 275
22. Varela J A., Saá C, Chem. Rev. 2003 103 3787
23. Henry G D., Tetrahedron 2004 60 6043
24. Bagley M C., Glover C, Merritt E A., Synlett 2007 2459
25. Movassaghi M, Hill M D., J. Am. Chem. Soc. 2006 128 4592
26. Movassaghi M, Hill M D., Ahmad O K., J. Am. Chem. Soc. 2007 129 10096
27. Lu J.-Y, Arndt H.-D, J. Org. Chem. 2007 72 4205
28. Craig D, Paina F, Smith S C., Chem. Commun. 2008 3408
29. Manning J R., Davies H M. L., J. Am. Chem. Soc. 2008 130 8602
30. Liu S, Liebeskind L S., J. Am. Chem. Soc. 2008 130 6918
31. Barluenga J, ángel M, Rodríguez F, García- García P, Aguilar E, J. Am. Chem. Soc. 2008 130 2764
32. Donohoe T J., Fishlock L P., Procopiou P A., Org. Lett. 2008 10 285
33. Beveridge R E., Arndtsen B A., Synthesis 2010 1000
34. Brown D J., In Comprehensive Heterocyclic Chemistry Vol. 3 Katritzky A R. Rees C W. ed Pergamon Oxford 1984 Chap. 2.13
35. Eicher T, Hauptmann S, Chemie der Heterocyclen Thieme Stuttgart 1994 398
36. Gilchrist T L., Heterocyclenchemie Neunhoeffer H ed Wiley-VCH Weinheim 1995 270
37. Hoffmann M G., In Houben-Weyl Vol. E9 Schaumann E ed Thieme Stuttgart 1996
38. Von Angerer S, Science of Synthesis Vol. 16 Yamamoto Y ed Thieme Stuttgart 2004 379
39. Müller T J. J., Braun R, Ansorge M, Org. Lett. 2000 2 1967
40. Sakai N, Aoki Y, Sasada T, Kanakahara T, Org. Lett. 2005 7 4705
41. Movassaghi M, Hill H D., J. Am. Chem. Soc. 2006 128 14254
42. Pinner A, Ber. Dtsch. Chem. Ges. 1890 23 2919
43. Pinner A, Ber. Dtsch. Chem. Ges. 1892 25 1414
44. Pinner A, Ber. Dtsch. Chem. Ges. 1895 28 483
45. Biginelli P, Ber. Dtsch. Chem. Ges. 1891 24 1317
46. Biginelli P, Ber. Dtsch. Chem. Ges. 1891 24 2962
47. Biginelli P, Ber. Dtsch. Chem. Ges. 1893 26 447
48. Kappe C O., J. Org. Chem. 1997 62 7203
49. Kappe C O., Bioorg. Med. Chem. Lett. 2000 10 49
50. Barthakur M G., Borthakur M, Devi P, Saikia C J., Saikia A, Bora U, Chetia A, Boruah R C., Synlett 2007 223
51. Hill M D., Movassaghi M, Chem. Eur. J. 2008 14 6836
52. Zimmer R, Synthesis 1993 165
53. Zimmer R, Khan F A., J. Prakt. Chem. 1996 338 92
54. Reissig H.-U, Hormuth S, Schade W, OkalaAmombo M G., Watanabe T, Pulz R, Hausherr A, Zimmer R, J. Heterocycl. Chem. 2000 37 597
55. Zimmer R, Reissig H.-U, In Modern Allene Chemistry Vol. 2 Krause N Hashmi A S. K. ed. Wiley-VCH Weinheim 2004 425-492
56. Reissig H.-U, Zimmer R, Science of Synthesis Vol. 44 Krause N Thieme Stuttgart 2007 301-352
57. Brasholz M, Reissig H.-U, Zimmer R, Acc. Chem. Res. 2009 42 45
58. Al-Harrasi A, Reissig H.-U, Angew. Chem. Int. Ed. 2005 44 6227
59. Angew Chem. 2005, 117, 6383
60. Kaden S, Reissig H.-U, Org. Lett. 2006 8 4763
61. Sörgel S, Azap C, Reissig H.-U, Org. Lett. 2006 8 4875
62. Brasholz M, Reissig H.-U, Angew. Chem. Int. Ed. 2007 46 1634
63. Angew. Chem. 2007, 119, 1659
64. Gwiazda M, Reissig H.-U, Synthesis 2008 990
65. Flögel O, Dash J, Brüdgam I, Hartl H, Reissig H.-U, Chem. Eur. J. 2004 10 4283
66. Dash J, Lechel T, Reissig H.-U, Org. Lett. 2007 9 5541
67. Eidamshaus C, Reissig H.-U, Adv. Synth. Catal. 2009 351 1162
68. Dash J, Reissig H.-U, Chem. Eur. J. 2009 15 6811
69. Lechel T, Dash J, Hommes P, Lentz D, Reissig H.-U, J. Org. Chem. 2010 75 726
70. Lechel T, Dash J, Eidamshaus C, Brüdgam I, Reissig H.-U, Org. Biomol. Chem. 2010 7 DOI: 10.1039/B925468D
71. Lechel T, Möhl S, Reissig H.-U, Synlett 2009 1059
72. Lechel T, Reissig H.-U, Eur. J. Org. Chem. 2010 2555
73. Lechel T, Dash J, Brüdgam I, Reissig H.-U, Eur. J. Org. Chem. 2008 3647
74. Miyaura N, Yamada K, Suzuki A, Tetrahedron Lett. 1979 20 3437
75. Miyaura N, Suzuki A, J. Chem. Soc., Chem. Commun. 1979 866
76. Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
77. Lindsay K B., Pyne S G., Aust. J. Chem. 2004 57 669
78. Riley H L., Morley J F., Friend N A. C., J. Chem. Soc. 1932 1875