Palladium-mediated three-component synthesis of furo[2,3-b]pyridones by one-pot coupling of 3-lodopyridones, alkynes, and organic halides

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2441-2444

  Bossharth, Emmanuel ^a   Desbordes, Philippe ^b   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

^b BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 IODOPYRIDONE; 4 ALKOXY 3 IODOPYRIDONE; ALKYNE; ALKYNE DERIVATIVE; FURO[2,3 B]PYRIDONE; HALIDE; ORGANIC COMPOUND; PALLADIUM; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; HETEROANNULATION REACTION; SYNTHESIS;

EID: 0141630849     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034644y     Document Type: Article

References (48)

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13. For recent reports, see: (a) Pirrung, M. C.; Blume, F. J. Org. Chem. 1999, 64, 3642-3649 and references therein. (b) Chang, G.-J.; Wu, M.-H.; Chen, W.-P.; Kuo, S.-C.; Su, M.-J. Drug Dev. Res. 2000, 50, 170-185. (c) Butenschön, I.; Möller, K.; Hänsel, W. J. Med. Chem. 2001, 44, 1249-1256. (d) Michael, J. P. Nat. Prod. Rep. 2001, 543-559 and previous annual reports.
14. For recent reports, see: (a) Pirrung, M. C.; Blume, F. J. Org. Chem. 1999, 64, 3642-3649 and references therein. (b) Chang, G.-J.; Wu, M.-H.; Chen, W.-P.; Kuo, S.-C.; Su, M.-J. Drug Dev. Res. 2000, 50, 170-185. (c) Butenschön, I.; Möller, K.; Hänsel, W. J. Med. Chem. 2001, 44, 1249-1256. (d) Michael, J. P. Nat. Prod. Rep. 2001, 543-559 and previous annual reports.
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19. For reactions involving carbonucleophiles, see: Balme, G.; Monteiro, N.; Bouyssi, D. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2245-2265. For oxygen nucleophiles, see: Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2193-2210. For nitrogen nucleophiles, see: Cacchi, S.; Marinelli, F. in Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2227-2244.
20. For reactions involving carbonucleophiles, see: Balme, G.; Monteiro, N.; Bouyssi, D. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2245-2265. For oxygen nucleophiles, see: Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2193-2210. For nitrogen nucleophiles, see: Cacchi, S.; Marinelli, F. in Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2227-2244.
21. For reactions involving carbonucleophiles, see: Balme, G.; Monteiro, N.; Bouyssi, D. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2245-2265. For oxygen nucleophiles, see: Cacchi, S.; Arcadi, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2193-2210. For nitrogen nucleophiles, see: Cacchi, S.; Marinelli, F. in Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley & Sons: New York, 2002; pp 2227-2244.
22. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
23. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
24. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
25. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
26. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
27. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
28. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
29. The methodology has already been successfully applied to the synthesis of other fused furans. Benzo[b]furans: (a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280-9288. (b) Cacchi, S.; Fabrizi, G.; Moro, L. Synlett 1998, 741-745. (c) Monteiro, N.; Balme, G. Synlett 1998, 746-747. (d) Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101-5104. (e) Monteiro, N.; Arnold, A.; Balme, G. Synlett 1998, 1111-1113. (f) Flynn, B. L.; Hamel, E.; Jung, M. K. J. Med. Chem. 2002, 45, 2670-2673. (g) Hu, Y.; Zhang, Y.; Yang, Z.; Fathi, R. J. Org. Chem. 2002, 67, 2365-2368. Furo[2,3-d]pyrimidin-2-ones: Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antiviral Chem. Chemother. 2001, 187-197.
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37. The one-pot realization of two consecutive, independent Pd-mediated reactions based on the use of a single Pd catalyst are rare. For recent examples related to multicomponent reactions, see: Grigg, R.; Mariani, E.; Sridharan, V. Tetrahedron Lett. 2001, 42, 8677-8680. Organ, M. G.; Arvanitis, E. A.; Dixon, C. E.; Cooper, J. T. J. Am. Chem. Soc. 2002, 124, 1288-1294. See also ref 8f.
38. The one-pot realization of two consecutive, independent Pd-mediated reactions based on the use of a single Pd catalyst are rare. For recent examples related to multicomponent reactions, see: Grigg, R.; Mariani, E.; Sridharan, V. Tetrahedron Lett. 2001, 42, 8677-8680. Organ, M. G.; Arvanitis, E. A.; Dixon, C. E.; Cooper, J. T. J. Am. Chem. Soc. 2002, 124, 1288-1294. See also ref 8f.
39. 0 source in similar reactions; see ref 9c.
40. Based on literature precedents, we had anticipated that further treatment of the reaction mixture with a source of halide would have been necessary. Sekar, M.; Prasad, J. R. J. Nat. Prod. 1998, 294-296.
41. II complexes are quite rare; see: Strukul, G. Top. Catal. 2002, 1, 33-42. Deacetalizations may be induced by palladium catalysts: Lipshutz, B. H.; Pollart, D.; Monforte, J.; Kotsuki, H. Tetrahedron Lett. 1985, 26, 705-708.
42. II complexes are quite rare; see: Strukul, G. Top. Catal. 2002, 1, 33-42. Deacetalizations may be induced by palladium catalysts: Lipshutz, B. H.; Pollart, D.; Monforte, J.; Kotsuki, H. Tetrahedron Lett. 1985, 26, 705-708.
43. The possibility that an arylpalladium halide may serve as a Lewis acid has been suggested recently. Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168-15169.
44. II acts simultaneously as transition-metal catalyst and Lewis acid has been reported recently. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
45. A similar trend was recently reported by Larock in the cyclization of o-alkynyl benzaldimines: Dai, G.; Larock, R. C. J. Org. Chem. 2003, 68, 920-928.
46. For multicomponent syntheses of symmetrical compounds involving bis-iodobenzene, see: (a) de Meijere, A.; Nüske, H.; Es-Sayed, M.; Labahn, T.; Schroen, M.; Bräse, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 3669-3672. (b) Azoulay, S.; Monteiro, N.; Balme, G. Tetrahedron Lett. 2002, 43, 9311-9314.
47. For multicomponent syntheses of symmetrical compounds involving bis-iodobenzene, see: (a) de Meijere, A.; Nüske, H.; Es-Sayed, M.; Labahn, T.; Schroen, M.; Bräse, S. Angew. Chem., Int. Ed. Engl. 1999, 38, 3669-3672. (b) Azoulay, S.; Monteiro, N.; Balme, G. Tetrahedron Lett. 2002, 43, 9311-9314.
48. See the Supporting Information for data of the X-ray single-crystal structure determination of compound 7i.