Novel 2-pyridone synthesis via nucleophilic addition of malonic esters to alkynyl imines

Organic Letters

Volumn 4, Issue 16, 2002, Pages 2755-2757

  Hachiya, Iwao ^a   Ogura, Kana ^a   Shimizu, Makoto ^a  

^a MIE UNIVERSITY   (Japan)

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ARTICLE;

EID: 0001040952     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026283c     Document Type: Article

References (24)

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11. Michael, E. J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Semmelhack, M. F., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp 1-67.
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13. For examples, see: Schultz, A. Z. Chem. Rev. 1973, 73, 385. Curran, D. P.; Liu H. J. Am. Chem. Soc. 1992, 114, 5863. Kozikowski, A. P.; Campiani, G.; Sun, L.-Q.; Wang, S.; Saxena, A.; Doctor, B. P. J. Am. Chem. Soc. 1996, 118, 11357. Williams, D. R.; Lowder, P. D.; Gu, Y.-G. Tetrahedron Lett. 1997, 38, 327.
14. For examples, see: Schultz, A. Z. Chem. Rev. 1973, 73, 385. Curran, D. P.; Liu H. J. Am. Chem. Soc. 1992, 114, 5863. Kozikowski, A. P.; Campiani, G.; Sun, L.-Q.; Wang, S.; Saxena, A.; Doctor, B. P. J. Am. Chem. Soc. 1996, 118, 11357. Williams, D. R.; Lowder, P. D.; Gu, Y.-G. Tetrahedron Lett. 1997, 38, 327.
15. For examples, see: Schultz, A. Z. Chem. Rev. 1973, 73, 385. Curran, D. P.; Liu H. J. Am. Chem. Soc. 1992, 114, 5863. Kozikowski, A. P.; Campiani, G.; Sun, L.-Q.; Wang, S.; Saxena, A.; Doctor, B. P. J. Am. Chem. Soc. 1996, 118, 11357. Williams, D. R.; Lowder, P. D.; Gu, Y.-G. Tetrahedron Lett. 1997, 38, 327.
16. For reviews, see: Smith, D. M. In Comprehensive Organic Chemistry; Sammes, P. G., Ed.; Pergamon: Oxford, 1979; Vol. 2, p 67. McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., McKillop, Eds.; Pergamon: Oxford, 1979; Vol. 1, p 3. Bailey, T. D.; Goe, G. L.; Scriven, E. F. V. In Heterocyclic Compounds; Newkome, G. R., Ed.; Wiley: New York, 1984; Vol. 14, Part 5, p 1. Jones, G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K.; Vol. 2A, p 395.
17. For reviews, see: Smith, D. M. In Comprehensive Organic Chemistry; Sammes, P. G., Ed.; Pergamon: Oxford, 1979; Vol. 2, p 67. McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., McKillop, Eds.; Pergamon: Oxford, 1979; Vol. 1, p 3. Bailey, T. D.; Goe, G. L.; Scriven, E. F. V. In Heterocyclic Compounds; Newkome, G. R., Ed.; Wiley: New York, 1984; Vol. 14, Part 5, p 1. Jones, G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K.; Vol. 2A, p 395.
18. For reviews, see: Smith, D. M. In Comprehensive Organic Chemistry; Sammes, P. G., Ed.; Pergamon: Oxford, 1979; Vol. 2, p 67. McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., McKillop, Eds.; Pergamon: Oxford, 1979; Vol. 1, p 3. Bailey, T. D.; Goe, G. L.; Scriven, E. F. V. In Heterocyclic Compounds; Newkome, G. R., Ed.; Wiley: New York, 1984; Vol. 14, Part 5, p 1. Jones, G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K.; Vol. 2A, p 395.
19. For reviews, see: Smith, D. M. In Comprehensive Organic Chemistry; Sammes, P. G., Ed.; Pergamon: Oxford, 1979; Vol. 2, p 67. McKillop, A.; Boulton, A. J. In Comprehensive Heterocyclic Chemistry; Boulton, A. J., McKillop, Eds.; Pergamon: Oxford, 1979; Vol. 1, p 3. Bailey, T. D.; Goe, G. L.; Scriven, E. F. V. In Heterocyclic Compounds; Newkome, G. R., Ed.; Wiley: New York, 1984; Vol. 14, Part 5, p 1. Jones, G. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K.; Vol. 2A, p 395.
20. For recent examples of the synthesis of functionalized 2-pyridones, see: Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis 1998, 1715 . Perrin, S.; Monnier, K.; Laude, B.; Kubicki, M.; Blacque, O. Eur. J. Org. Chem. 1999, 297. Brun, E. M.; Ramón, M.; Parra, M. Synlett 1999, 1088. Bondavalli, F.; Bruno, O.; Lo Presti, E.; Mosti, L. Synthesis 1999, 1169.
21. For recent examples of the synthesis of functionalized 2-pyridones, see: Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis 1998, 1715 . Perrin, S.; Monnier, K.; Laude, B.; Kubicki, M.; Blacque, O. Eur. J. Org. Chem. 1999, 297. Brun, E. M.; Ramón, M.; Parra, M. Synlett 1999, 1088. Bondavalli, F.; Bruno, O.; Lo Presti, E.; Mosti, L. Synthesis 1999, 1169.
22. For recent examples of the synthesis of functionalized 2-pyridones, see: Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis 1998, 1715 . Perrin, S.; Monnier, K.; Laude, B.; Kubicki, M.; Blacque, O. Eur. J. Org. Chem. 1999, 297. Brun, E. M.; Ramón, M.; Parra, M. Synlett 1999, 1088. Bondavalli, F.; Bruno, O.; Lo Presti, E.; Mosti, L. Synthesis 1999, 1169.
23. For recent examples of the synthesis of functionalized 2-pyridones, see: Furukawa, I.; Fujisawa, H.; Kawazome, M.; Nakai, Y.; Ohta, T. Synthesis 1998, 1715 . Perrin, S.; Monnier, K.; Laude, B.; Kubicki, M.; Blacque, O. Eur. J. Org. Chem. 1999, 297. Brun, E. M.; Ramón, M.; Parra, M. Synlett 1999, 1088. Bondavalli, F.; Bruno, O.; Lo Presti, E.; Mosti, L. Synthesis 1999, 1169.
24. For a recent example of the synthesis of N-aryl-5-alkoxycarbonyl-2-pyridones, see: Ko, Y. K.; Lee, S. C.; Koo, D. W.; Jung, M.; Kim, D.-W. Bull. Korean Chem. Soc. 2001, 22, 234 references therein.