Novel furo-pyridine derivatives via sonogashira reactions of functionalized pyridines

European Journal of Organic Chemistry

Volumn , Issue 21, 2008, Pages 3647-3655

  Lechel, Tilman ^a   Dash, Jyotirmayee ^a   Brüdgam, Irene ^a   Reißig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Allenes; Fluorescence; Furo pyridines; Palladium catalysis; Pyridines

Indexed keywords

EID: 49649084787     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800398     Document Type: Article

References (51)

1. a) O. Flögel, J. Dash, I. Brüdgam, H. Hartl, H.-U. Reißig, Chem. Eur. J. 2004, 10, 4283-4290;
2. b) H.-U. Reißig, O. Flögel, German Patent Application, DE 103 36 497 A1 (3.3.2005).
3. J. Dash, T. Lechel, H.-U. Reißig, Org. Lett. 2007, 9, 5541-5544.
4. For recent applications of the particularly useful alkenyl- and arylnonaflates see: J. Högermeier, H.-U. Reißig, Chem. Eur. J. 2007, 13, 2410-2420 and references cited in this publication.
5. Selected reviews: a) K. Sonogashira, in Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.: E.-i. Negishi, A. de Meijere), Wiley, New York, 2002, pp. 493-529;
6. b) K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49;
7. c) J. A. Marsden, M. M. Haley, in Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004, pp. 317-394;
8. d) E.-i. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-2017;
9. e) R. Chinchilla, C. Nájera, Chem. Rev. 2007, 107, 874-922;
10. f) H. Doucet, J.-C. Hierso, Angew. Chem. 2007, 119, 850-888;
11. Angew. Chem. Int. Ed. 2007, 46, 834-871.
12. For reviews on furo-pyridines: a) W. Friedrichsen, in Comprehensive Heterocyclic Chemistry, vol. 4 (Eds.: A. R. Katritzky, C. W. Rees), Pergamon Press, New York, 1984, pp. 974-1036;
13. b) S. Shiotani, Heterocycles 1997, 45, 975-1011;
14. c) S. Cacchi, G. Fabrizi, A. Goggiomani, Heterocycles 2002, 56, 613-632;
15. d) H. van de Poël, G. Guillaumet, M.-C. Viaud-Massuard, Heterocycles 2002, 57, 55-71;
16. for reviews including furo-pyridines: e) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127-2198;
17. f) G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285-2309;
18. g) R. C. Larock, in Acetylene Chemistry (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, New York, 2005, pp. 55-91.
19. For recent syntheses of furo-pyridine derivatives: a) I. N. Houpis, W. B. Choi, P. J. Reider, A. Molina, H. Churchill, J. Lynch, R. P. Volante, Tetrahedron Lett. 1994, 35, 9355-9358;
20. b) D. G. Wishka, D. R. Graber, E. P. Seest, L. A. Dolak, F. Han, W. Watt, J. Morris, J. Org. Chem. 1998, 63, 7851-7859;
21. c) W.-T. Li, F.-C. Lai, G.-H. Lee, S.-M. Peng, R.-S. Liu, J. Am. Chem. Soc. 1998, 120, 4520-4521;
22. d) A. Arcadi, S. Cacchi, S. D. Giuseppe, G. Fabrizi, F. Marinelli, Synlett 2002, 453-457;
23. e) W. S. Yue, J. J. Li, Org. Lett. 2002, 4, 2201-2203;
24. f) A. Arcadi, S. Cacchi, S. di Giuseppe, G. Fabrizi, F. Marinelli, Org. Lett. 2002, 4, 2409-2412;
25. g) A. Fayol, J. Zhu, Org. Lett. 2004, 6, 115-118;
26. h) P. Cironi, J. Tulla-Puche, G. Barany, F. Albericio, M. Alvarez, Org. Lett. 2004, 6, 1405-1408;
27. i) I. Aillaud, E. Bossharth, D. Conreaux, P. Desbordes, N. Monteiro, G. Balme, Org. Lett. 2006, 8, 1113-1116.
28. a) M. Gwiazda, H.-U. Reißig, Synlett 2006, 1683-1686;
29. b) M. Gwiazda, H.-U. Reißig, Synthesis 2008, 990-994.
30. For reviews on alkoxyallenes: a) R. Zimmer, Synthesis 1993, 165-178;
31. b) R. Zimmer, F. A. Khan, J. Prakt. Chem. 1996, 338, 92-94;
32. c) R. Zimmer, H.-U. Reißig, Donor-Substituted Allenes in Modern Allene Chemistry (Eds.: N. Krause, A. S. K. Hashmi), Wiley-VCH, Weinheim, 2004, 425-492;
33. d) H.-U. Reißig, R. Zimmer, Science of Synthesis, vol. 44 (Ed.: N. Krause), Thieme, Stuttgart,2007, 301-352;
34. e) M. Brasholz, H.-U. Reißig, R. Zimmer, Acc. Chem. Res., in press;
35. for selected recent applications developed by our group see: f) A. Al-Harrasi, H.-U. Reißig, Angew. Chem. 2005, 117, 6383-6387;
36. Angew. Chem. Int. Ed. 2005, 44, 6227-6231;
37. g) S. Kaden, H.-U. Reißig, Org. Lett. 2006, 8, 4763-4766;
38. h) S. Sörgel, C. Azap, H.-U. Reißig, Org. Lett. 2006, 8, 4875-4878;
39. i) M. Brasholz, H.-U. Reißig, Angew. Chem. 2007, 119, 1659-1662;
40. Angew. Chem. Int. Ed. 2007, 46, 1634-1637.
41. For a review on Glaser-type couplings to dialkynes, see: P. Siemsen, R. C. Livingston, F. Diederich, Angew. Chem. 2000, 112, 2740-2767;
42. Angew. Chem. Int. Ed. 2000, 39, 2632-2657.
43. CCDC-675677 (for 13) contains the supplementary crystallographic data. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
44. Iodine and NIS failed to induce this cyclization. For a related reaction employing ICl, see: D. Yue, T. Yao, R. C. Larock, J. Org. Chem. 2005, 70, 10292-10296.
45. For a recent thematic issue on organic electronics and optoelectronics: a) S. R. Forrest, M. E. Thompson, Chem. Rev. 2007, 107, 923-1386;
46. also see: b) K. Müllen, U. Scherf, Organic Light-Emitting Devices: Synthesis Properties and Applications, Wiley-VCH, Weinheim, 2006;
47. c) T. J. J. Müller, U. H. F. Bunz, Functional Organic Materials, Wiley-VCH, Weinheim, 2007.
48. For an original report dealing with light-emitting CF3-substituted pyridine derivatives: d) Y. Yamaguchi, T. Tanaka, S. Kobayashi, T. Wakamiya, Y. Matsubara, Z.-i. Yoshida, J. Am. Chem. Soc. 2005, 127, 9332-9333.
49. For a recent synthesis of pyrazolo[3,4-c]pyridines: T. S. Heller, S. R. Natarajan, Org. Lett. 2007, 9, 4947-4950.
50. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467-473.
51. G. M. Sheldrick, a program for refining crystal structures, University of Göttingen, Germany, 1997.