Multi-component syntheses of heterocycles initiated by palladium catalyzed generation of alkynones and chalcones

Chimica Oggi

Volumn 25, Issue 1, 2007, Pages 70-78

  Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

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EID: 33847659705     PISSN: 0392839X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (69)

1. For a recent monography, see e. g. "Multicomponent Reactions", J. Zhu, H. Bienaymé, eds., Wiley-VCH, Weinheim, 2005.
2. For reviews, see e. g. a) H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 6, pp. 3321-3329 (2000).
3. b) A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39, pp. 3168-3210 (2000).
4. c) I. Ugi, A. Dömling, B. Werner, B. J. Heterocycl. Chem. 37, pp. 647-658 (2000).
5. d) L. Weber, K. Illgen, M. Almstetter, Synlett, pp. 366-374 (1999).
6. e) R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res. 29, pp. 123-131 (1996).
7. f) I. Ugi, A. Dömling, W. Hörl, Endeavour, 18, pp. 115-122 (1994).
8. g) G.H. Posner, Chem. Rev. 86, pp. 831-844 (1986).
9. For reviews on diversity oriented syntheses, see e. g. a) S.L. Schreiber, M.D. Burke, Angew. Chem. Int. Ed. 43, pp. 46-58 (2004).
10. b) M.D. Burke, E.M. Berger, S.L. Schreiber, Science 302, pp. 613-618 (2003).
11. c) P. Arya, D.T.H. Chou, M.G. Baek, Angew. Chem. Int. Ed. 40, pp. 339-346 (2001).
12. d) B. Cox, J.C. Denyer, A. Binnie, M. C. Donnelly, B. Evans, D.V.S. Green, J.A. Lewis, T.H. Mander, A.T. Merritt, M.J. Valler, S.P. Watson, Progr. Med. Chem. 37, pp. 83-133 (2000).
13. e) S.L. Schreiber, Science 287, pp. 1964-1969 (2000).
14. For leading reviews on combinatorial chemistry, see e. g. a) Combinatorial Chemistry - Synthesis, Analysis, Screening, G. Jung, ed., Wiley-VCH, Weinheim, 1999.
15. b) F. Balkenhohl, C. von dem Bussche-Hünnefeld, A. Lansky, C. Zechel, Angew. Chem. Int. Ed. Engl. 35, pp. 2288-2337 (1996).
16. S. Kobayashi, Chem. Soc. Rev. 28, pp. 1-15 (1999).
17. For syntheses of pyrazoles, see, e. g. a) C. Moureu, R. Delange, Bull. Soc. Chim. Fr. 25, pp. 302-313 (1901).
18. b) R.D. Miller, O. Reiser, J. Heterocycl. Chem. 30, pp. 755-763 (1993).
19. c) D.B. Grotjahn, S. Van, D. Combs, D.A. Lev, C. Schneider, M. Rideout, C. Meyer, G. Hernandez, L. Mejorado, J. Og. Chem. 67, pp. 9200-9209 (2002).
20. For syntheses of isoxazoles, see, e. g. a) K. Bowden, E.R.H. Jones, J. Chem. Soc. 25, pp. 953-954 (1946).
21. b) R.M. Adlington, J.E. Baldwin, D. Catterick, G.J. Pritchard, L.T. Tang, J. Chem. Soc. Perkin Trans. 1, pp. 303-305 (2000).
22. For syntheses of pyrimidines, see, e. g. a) R.M. Adlington, J.E. Baldwin, D. Catterick, G.J. Pritchard, Chem. Commun., pp. 1757-1758 (1997).
23. b) M.C. Bagley, D.D. Hughes, P.H. Taylor, X. Xiong, Synlett, pp. 259-261 (2003).
24. c) M.C. Bagley, D. D. Hughes, H.M. Sabo, P.H. Taylor, X. Xiong, Synlett, pp. 1443-1446 (2003).
25. For syntheses of pyridines, see, e. g. a) F. Bohlmann, D. Rahtz, Chem. Ber. 90, pp. 2265-2272 (1957).
26. b) M.C. Bagley, C. Brace, J.W. Dale, M. Ohnesorge, N.G. Philips X. Xiong, J. Bower, J. Chem. Soc. Perkin Trans. 1, pp. 1663-1671 (2002).
27. c) M.C. Bagley, J.W. Dale, M. Ohnesorge, N.G. Philips X. Xiong, J. Bower, J. Comb. Chem. 5, pp. 41-44 (2003).
28. For syntheses of pyridines from 1,3-diaryl propenones, see e. g. a) D.G. Powers, D.S. Casebier, D. Fokas, W.J. Ryan, J.R. Troth, D.L. Coffen, Tetrahedron 54, pp. 4085-4096 (1998).
29. b) K. Shibata, I. Katsuyama, H. Izoe, M. Matsui, H. Muramatsu, J. Heterocycl. Chem. 30, pp. 277-281 (1993).
30. c) M. Matsui, A. Oji, K. Hiramatsu, K. Shibata, H. Muramtsu, J. Chem. Soc. Perkin Trans. 2, pp. 201-206 (1992).
31. For syntheses of pyrimidines from 1,3-diaryl propenones, see e. g. a) R.M. Dodson, J.K. Seyler, J. Org. Chem. 16, pp. 461-465 (1951).
32. b) F.H. Al-Hajjar, S.S. Sabri, J. Heterocycl. Chem. 19, pp. 1087-1092 (1982).
33. c) D. Simon, O. Lafont, C.C. Farnoux, M. Miocque, J. Heterocycl. Chem. 22, pp. 1551-1557 (1985).
34. d) D.W. Boykin, A. Kumar, M. Bajic, G. Xiao, W.D. Wilson, B.C. Bender, D.R. McCurdy, J.E. Hall, R.R. Tidwell, Eur. J. Med. Chem. 32, pp. 965-972 (1997).
35. For syntheses of 1,5-benzoheteroazepines from 1,3-diaryl propenones, see e. g. a) R.A. Mane, D.B. Ingle, Indian J. Chem., Sect. B, 21B, pp. 973-974 (1982).
36. b) K.P. Jadhav, D.B. Ingle, Indian J. Chem., Sect. B, 22B, pp. 180-182 (1983).
37. c) A. Attia, O.I. Abdel-Salam, M.H. Abo-Ghalia, A.E. Amr, Egypt. J. Chem. 38, pp. 543-553 (1995).
38. d) R.J. Reddy, D. Ashok, P.N. Sarma, Indian J. Chem., Sect. B, 32B, pp. 404-406 (1993).
39. e) K. Satyanarayana, M.N.A. Rao, Indian J. Pharm. Sci. 55, pp. 230-233 (1993).
40. f) G. De Sarro, A. Chimirri, A. De Sarro, R. Gitto, S. Grasso, M. Zappala, Eur. J. Med. Chem. 30, pp. 925-929 (1995).
41. g) D. Lloyd, H. McNab, Adv. Heterocycl. Chem. 71, 1-56 (1998).
42. For the review on the chemistry of ynones, see: R.A. Bol'shedvorskaya, L.I. Vereshchagin, Russ. Chem. Rev. 42, pp. 225-240 (1973).
43. For a review on the chemistry of 1,3-diaryl propenones, see e. g. C. Thebtaranonth, Y. Thebtaranonth, in The Chemistry of Enones, S. Patai, Z. Rappoport, Hrsg., J. Wiley & Sons, Chichester, New York, Brisbane, Toronto, Singapore, Vol. 29, pp. 199-280 (1989).
44. For lead reviews on Sonogashira couplings, see e.g. a) S. Takahashi, Y. Kuroyama, K. Sonogashira, N. Hagihara, Synthesis, pp. 627-630 (1980).
45. b) K. Sonogashira, in Metal Catalyzed Cross-coupling Reactions, F. Diederich, P.J. Stang, eds., Wiley-VCH, Weinheim, pp. 203-229 (1998).
46. c) K. Sonogashira, J. Organomet. Chem., 653(1-2), pp. 46-49 (2002).
47. d) E.-I. Negishi, L. Anastasia, Chem. Rev. 103, pp. 1979-2018 (2003).
48. a) Y. Tohda, K. Sonogashira, N. Hagihara, Synthesis, pp. 777-778 (1977).
49. b) T.E. Nielsen, M.A. Cubillo de Dios, D. Tanner, J. Org. Chem. 67, pp. 7309-7313 (2002).
50. c) D.A. Alonso, C. Najera, M.C. Pacheco, J. Org. Chem. 69, pp. 1615-1619 (2004).
51. A.S. Karpov, T.J.J. Müller, Org. Lett. 5, pp. 3451-3454 (2003).
52. A.S. Karpov, T.J.J. Müller, Synthesis, pp. 2815-2826 (2003).
53. a) A.S. Karpov, T. Oeser, T.J.J. Müller, Chem. Commun., pp. 1502-1503 (2004).
54. b) A.S. Karpov, F. Rominger, T.J.J. Müller, Org. Biomol. Chem., pp. 4382-4391 (2005).
55. a) A.S. Karpov, E. Merkul, T. Oeser, T.J.J. Müller, Chem. Commun., pp. 2581-2583 (2005).
56. b) A.S. Karpov, E. Merkul, T. Oeser, T.J.J. Müller, Eur. J. Org. Chem., pp. 2991-3000 (2006).
57. a) M.S.M. Ahmed, A. Mori, Org. Lett., 5, pp. 3057-3060 (2003).
58. b) M.S.M. Ahmed, K. Kobayashi, A. Mori, Org. Lett. 7, pp. 4487-4489 (2005).
59. A.S. Karpov, E. Merkul, F. Rominger, T.J.J. Müller, Angew. Chem. Int. Ed. 44, pp. 6951-6956 (2005).
60. T.J.J. Müller, M. Ansorge, D. Aktah, Angew. Chem. Int. Ed. 39, pp. 1253-1256 (2000).
61. T.J.J. Müller, R. Braun, M. Ansorge, Org. Lett. 2, pp. 1967-1970 (2000).
62. a) R.U. Braun, T.J.J. Müller, Tetrahedron 60, pp. 9463-9469 (2004).
63. b) R.U. Braun, K. Zeitler, T.J.J. Müller, Org. Lett. 2, pp. 4181-4184 (2000).
64. a) R.U. Braun, T.J.J. Müller, Synthesis, pp. 2391-2406 (2004).
65. b) R.U. Braun, K. Zeitler, T.J.J. Müller, Org. Lett. 3, pp. 3297-3300 (2001).
66. a) N.A.M. Yehia, K. Polborn, T.J.J. Müller, Tetrahedron Lett. 43, pp. 6907-6910 (2002).
67. b) O.G. Dediu, N.A.M. Yehia, T. Oeser, K. Polborn, T.J.J. Müller, Eur. J. Org. Chem., pp. 1834-1858 (2005).
68. O. G. Dediu, N.A.M. Yehia, T.J.J. Müller, Z. Naturforsch. 59b, pp. 443-450 (2004).
69. O.G. Schramm, née Dediu, T. Oeser, T.J.J. Müller, J. Org. Chem. 71, pp. 3494-3500 (2006).