Regio- and selective synthesis of 4,6-disubstituted-2-pyridones

Tetrahedron Letters

Volumn 44, Issue 31, 2003, Pages 5791-5794

  Cherry, Khalil ^a   Abarbri, Mohamed ^a   Parrain, Jean Luc ^b   Duchêne, Alain ^a  

^a UNIVERSITÉ DE TOURS   (France)

^b Lab Synt Organique Associe CNRS   (France)

Author keywords

2 pyridones; Coupling reactions; Palladium catalyst; Tributylstannylallenes

Indexed keywords

PYRIDONE DERIVATIVE;

ARTICLE; KNOEVENAGEL CONDENSATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038646645     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01429-1     Document Type: Article

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18. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
19. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
20. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
21. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
22. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
23. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
24. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
25. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
26. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
27. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
28. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
29. For recent and various synthesis methods, see: (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50; (b) Deodhar, K.; Kekare, M.; Pednekar, S. Synthesis 1985, 328; (c) Barluenga, J.; Tomǎs, M.; Suǎrez-Sobrino, A.; Gotor, V. Tetrahedron Lett. 1988, 29, 4855; (d) Chandra Sheker Reddy, A.; Narsaiah, B.; Venkataratnam, R. Tetrahedron Lett. 1996, 37, 2829; (e) Takaoka, K.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1996, 37, 4973; (f) Katritzky, A.; Belyakov, S.; Sorochinsky, A.; Henderson, S.; Chen, J. J. Org. Chem. 1997, 62, 6210; (g) Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis, 1998, 1715; (h) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.; Beaudegnies, R. Tetrahedron 1999, 55, 3387; (i) Grosche, P.; Höltzel, A.; Walk, T.; Trautwein, A.; Jung, G. Synthesis, 1999, 1961; (j) Zhang, S.; Liebeskind, L. J. Org. Chem. 1999, 64, 4042; (k) Alberola, A.; Calvo, L.; Ortega, A.; Carmen Sanudo Ruiz, M.; Yustos, P. J. Org. Chem. 1999, 64, 9493; (l) Brun, E.; Gil, S.; Mestres, R.; Parra, M. Synthesis 2000, 273; (m) Paulvannan, K.; Chen, T. J. Org. Chem. 2000, 65, 6160.
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