A New Modification of the Friedländer Synthesis via ortho-Dilithiated N-Pivaloylanilines

Synlett

Volumn 1997, Issue 3, 1997, Pages 285-286

  Ubeda, J Ignacio ^a   Villacampa, Mercedes ^a   Avendaño, Carmen ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002529642     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-773     Document Type: Article

References (18)

1. Friedländer, P. Ber. 1882, 15, 2572.
2. Eldelfield, R. C. In The Chemistry of Heterocyclic Compounds, Vol. 4; Eldelfield, R. C., Ed.; John Wiley & Sons, 1952; p 45.
3. Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37.
4. Jones, G. In The Chemistry of Heterocyclic Compounds. Quinoline. Part 1; Jones, G., Ed.; John Wiley & Sons, 1977; p 181.
5. Park, D. J.; Fulmer, T. D.; Beam, Ch. F. J. Heterocyclic Chem. 1981, 18, 649.
6. See for instance: Gronowitz, S.; Westerlund, C.; Hörnfeldt, A.-B. Acta Chem. Scand. B 1975, 29, 7.
7. See for instance: Watanabe, Y.; Takatsuki, K.; S. Ch. Shim; Mitsudi, T-a.; Takegami, Y. Bull. Chem. Soc. (Japan) 1978, 51, 3397.
8. Cho, I,- S.; Gong, L.; Muchowski, J. M. J. Org. Chem. 1991, 56, 7288.
9. Chen, L-Ch.; Lin, J-H.; Wu, S-S. J. Chin. Chem. Soc. 1984, 31, 413.
10. a) Capuano, L.; Ahlhelm, A.; Hartmann, H. Chem. Ber. 1986, 119, 2029.
11. b) Ferrer, P.; Avendaño, C.; Söllhuber, M. Liebigs Ann. 1995, 1895.
12. Turner, J. A. J. Org. Chem. 1990, 55, 4744.
13. For other examples of ortho-directed lithiation of pivaloyl anilines see for example: a) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133. b) Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4758. c) Tamura, Y.; Fujita, M.; Chen, L.-Ch.; Inoue, M.; Kita, Y. J. Org. Chem. 1981, 46, 3564. d) Reed, J. N.; Rotchford, J.; Stricklan, D. Tetrahedron Lett. 1988, 29, 5725. e) Hewawasam, P.; Meanwell, N. A. Tetrahedron Lett. 1994, 35, 7303.
14. For other examples of ortho-directed lithiation of pivaloyl anilines see for example: a) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133. b) Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4758. c) Tamura, Y.; Fujita, M.; Chen, L.-Ch.; Inoue, M.; Kita, Y. J. Org. Chem. 1981, 46, 3564. d) Reed, J. N.; Rotchford, J.; Stricklan, D. Tetrahedron Lett. 1988, 29, 5725. e) Hewawasam, P.; Meanwell, N. A. Tetrahedron Lett. 1994, 35, 7303.
15. For other examples of ortho-directed lithiation of pivaloyl anilines see for example: a) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133. b) Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4758. c) Tamura, Y.; Fujita, M.; Chen, L.-Ch.; Inoue, M.; Kita, Y. J. Org. Chem. 1981, 46, 3564. d) Reed, J. N.; Rotchford, J.; Stricklan, D. Tetrahedron Lett. 1988, 29, 5725. e) Hewawasam, P.; Meanwell, N. A. Tetrahedron Lett. 1994, 35, 7303.
16. For other examples of ortho-directed lithiation of pivaloyl anilines see for example: a) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133. b) Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4758. c) Tamura, Y.; Fujita, M.; Chen, L.-Ch.; Inoue, M.; Kita, Y. J. Org. Chem. 1981, 46, 3564. d) Reed, J. N.; Rotchford, J.; Stricklan, D. Tetrahedron Lett. 1988, 29, 5725. e) Hewawasam, P.; Meanwell, N. A. Tetrahedron Lett. 1994, 35, 7303.
17. For other examples of ortho-directed lithiation of pivaloyl anilines see for example: a) Fuhrer, W.; Gschwend, H. W. J. Org. Chem. 1979, 44, 1133. b) Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4758. c) Tamura, Y.; Fujita, M.; Chen, L.-Ch.; Inoue, M.; Kita, Y. J. Org. Chem. 1981, 46, 3564. d) Reed, J. N.; Rotchford, J.; Stricklan, D. Tetrahedron Lett. 1988, 29, 5725. e) Hewawasam, P.; Meanwell, N. A. Tetrahedron Lett. 1994, 35, 7303.
18. 3) δ 13.0, 19.3, 29.5, 55.6, 103.6, 119.6, 120.8, 128.2, 128.6, 130.6, 147.5, 154.7, 163.5.