Preparation of highly substituted 4-aminopyridones via the reaction of 2-methylene dihydrobenzimidazole with vinyl isocyanates

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1151-1153

  Rigby, James H ^a   Lee, Chee Seng ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLENE DIHYDROBENZIMIDAZOLE; IMIDAZOLE DERIVATIVE; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; CYCLIZATION; SYNTHESIS;

EID: 0141518672     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034263k     Document Type: Article

References (27)

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15. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
16. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
17. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
18. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
19. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
20. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
21. For other pyridone syntheses, see: (a) Overman, L. E.; Tsuboi, S.; Roos, J. P.; Taylor, G. F. J. Am. Chem. Soc. 1980, 102, 747-754. (b) Saunte, F.; Serckx-Ponci, B.; Hesbain-Frisque, A.-M.; Ghosez, L. J. Am. Chem. Soc. 1982, 104, 1428-1430. (c) Winters, G.; Sala, A.; DePaoli, A.; Ferri, V. Synthesis 1984, 1052. (d) Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T. J. Org. Chem. 1999, 64, 2038-2049. (e) Alberola, A.; Calvo, L. A.; Ortega, A. G.; Ruiz, M. C.; Yustos, P.; Granda, G.; Garcia-Rodriguez, E. J. Org. Chem. 1999, 64, 9493-9498. (f) Carles, L.; Narkunan, K.; Penlou, S.; Rousset, L.; Bouchu, D.; Ciufolini, M. A. J. Org. Chem. 2002, 67, 4304-4308. (g) Savarin, C. G.; Murry, J. A.; Dormer, P. G. Org. Lett. 2002, 4, 2071-2074.
22. 13C NMR, IR) and analytical (HRMS) data fully consistent with the assigned structures.
23. Standard conditions: a solution of acyl azide (1 equiv) in benzene or acetonitrile was refluxed for 1 h and then cooled to 0°C. A solution of 2-methylene dihydrobenzimidazole in benzene or acetonitrile was added, and the reaction was stirred at room temperature for 30 min and then refluxed for 2 h, concentrated, and purified by column chromatography.
24. (a) Rigby, J. H.; Laurent, S. J. Org. Chem. 1999, 64, 1766-1767.
25. (b) Rigby, J. H.; Laurent, S.; Dong, W.; Danca, M. D. Tetrahedron, 2000, 56, 10101-10111.
26. Hydrolysis of the enamides has been problematic, but studies continue in this direction.
27. For studies on the nucleophilicity of these species, see: Kuhn, N.; Bohnen, H.; Kruetzberg, J.; Blaser, D.; Boese, R. J. Chem. Soc., Commun. 1993, 1136.