Palladium-catalyzed rearrangement/arylation of 2-allyloxypyridine leading to the synthesis of n-substituted 2-pyridones

Organic Letters

Volumn 5, Issue 12, 2003, Pages 2161-2164

  Itami, Kenichiro ^a   Yamazaki, Daisuke ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ALLYLOXYPYRIDINE; 2 PYRIDONE DERIVATIVE; PALLADIUM COMPLEX; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0141742434     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0346234     Document Type: Article

References (39)

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26. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
27. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
28. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
29. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
30. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
31. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
32. Pd(II)-catalyzed rearrangement of allyl imidates: (a) Overman, L. E. Acc. Chem. Res. 1980, 13, 218. (b) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579. (c) Ikariya, T.; Ishikawa, Y.; Hirai, K.; Yoshikawa, S. Chem. Lett. 1982, 1815. (d) Schenck, T. G.; Bosnich, B. J. Am. Chem. Soc. 1985, 107, 2058. (e) Metz, P.; Mues, C.; Schoop, A. Tetrahedron 1992, 48, 1071. (f) Gonda, J.; Helland, A. C.; Ernst, B.; Belluš, D. Synthesis 1993, 729. (g) Calter, M.; Hollis, T. K.; Overman, L. E.; Ziller, J.; Zipp, G. G. J. Org. Chem. 1997, 62, 1449. (h) Uozumi, Y.; Kato, K.; Hayashi, T. Tetrahedron: Asymmetry 1998, 9, 1065.
33. Pd(0)-catalyzed rearrangement of allyl imidates: ref 11c,d.
34. 3 catalyst for Mizoroki-Heck reaction: Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
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36. 3 catalytic system, 6a was obtained in 16% yield after 96 h at 100°C. Phenyl triflate was a totally ineffective arylating agent in this reaction.
37. Toluene can also be used as a solvent in place of xylenes.
38. 13 may be generated in situ during the rearrangement reaction.
39. 3 (154.3 mg, 0.56 mmol), and dry xylenes (0.5 mL). After the resultant mixture was stirred at 100°C for 22 h, the catalyst and inorganic salts were removed by filtration through a short silica gel pad (EtOAc). The filtrate was evaporated, and the residue was chromatographed on silica gel (hexane/EtOAc = 1/1) to afford 6d (90.8 mg, 95%) as pale yellow oil.