Preparation of 3-haloquinolines from 3-amino-2-halo-2-alkenimines

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7195-7197

  Campos, Pedro J ^a   Tan, Cheng Quan ^a,b   Rodríguez, Miguel A ^a   Añón, Elena ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b DALIAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000394318     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9600215     Document Type: Article

References (25)

1. (a) Kametani, T.; Kasai, H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Eisevier Scientific Publishing Co.: Amsterdam, 1989; Vol. 3, p 385.
2. (b) Yates, F. S. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; Vol. 2, p 511.
3. (c) Sainsbury, M. In Rodd's Chemistry of Carbon Compounds; Coffey, S., Ed.; Eisevier Scientific Publishing Co.: Amsterdam, 1978; Part G. p 171.
4. For reviews of methods for the synthesis of quinoline derivatives see: (a) Jones, G. In ref 1a; p 395. (b) Campbell, N. In ref 1c; 1976; Part F, p 235. (c) Newkome, G. R.; Paudler, W. W. Contemporary Heterocydic Chemistry. Syntheses, Reactions, and Applications; Wiley: New York, 1982; p 200. (d) Gilchrist, T. L. Heterocyclic Chemistry, 2nd ed.; Longman Scientific & Technical: Essex, U.K., 1992; p 152. (e) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p 120.
5. For reviews of methods for the synthesis of quinoline derivatives see: (a) Jones, G. In ref 1a; p 395. (b) Campbell, N. In ref 1c; 1976; Part F, p 235. (c) Newkome, G. R.; Paudler, W. W. Contemporary Heterocydic Chemistry. Syntheses, Reactions, and Applications; Wiley: New York, 1982; p 200. (d) Gilchrist, T. L. Heterocyclic Chemistry, 2nd ed.; Longman Scientific & Technical: Essex, U.K., 1992; p 152. (e) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p 120.
6. For reviews of methods for the synthesis of quinoline derivatives see: (a) Jones, G. In ref 1a; p 395. (b) Campbell, N. In ref 1c; 1976; Part F, p 235. (c) Newkome, G. R.; Paudler, W. W. Contemporary Heterocydic Chemistry. Syntheses, Reactions, and Applications; Wiley: New York, 1982; p 200. (d) Gilchrist, T. L. Heterocyclic Chemistry, 2nd ed.; Longman Scientific & Technical: Essex, U.K., 1992; p 152. (e) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p 120.
7. For reviews of methods for the synthesis of quinoline derivatives see: (a) Jones, G. In ref 1a; p 395. (b) Campbell, N. In ref 1c; 1976; Part F, p 235. (c) Newkome, G. R.; Paudler, W. W. Contemporary Heterocydic Chemistry. Syntheses, Reactions, and Applications; Wiley: New York, 1982; p 200. (d) Gilchrist, T. L. Heterocyclic Chemistry, 2nd ed.; Longman Scientific & Technical: Essex, U.K., 1992; p 152. (e) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p 120.
8. For reviews of methods for the synthesis of quinoline derivatives see: (a) Jones, G. In ref 1a; p 395. (b) Campbell, N. In ref 1c; 1976; Part F, p 235. (c) Newkome, G. R.; Paudler, W. W. Contemporary Heterocydic Chemistry. Syntheses, Reactions, and Applications; Wiley: New York, 1982; p 200. (d) Gilchrist, T. L. Heterocyclic Chemistry, 2nd ed.; Longman Scientific & Technical: Essex, U.K., 1992; p 152. (e) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p 120.
9. Newhouse, B. J.; Bordner, J.; Augeri, D. J.; Litts, C. S.; Kleinman, E. F. J. Org. Chem. 1992, 57, 6991. Torii, S.; Xu, L. H.; Sadakane, M.; Okumoto, H. Synlett 1992, 513.
10. Newhouse, B. J.; Bordner, J.; Augeri, D. J.; Litts, C. S.; Kleinman, E. F. J. Org. Chem. 1992, 57, 6991. Torii, S.; Xu, L. H.; Sadakane, M.; Okumoto, H. Synlett 1992, 513.
11. Campos, P. J.; Tan, C.-Q.; González, J. M.; Rodríguez, M. A. Tetrahedron Lett. 1993, 34, 5321.
12. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; Rodríguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567. Barluenga, J.; González, J. M.; García-Martin, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
13. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; Rodríguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567. Barluenga, J.; González, J. M.; García-Martin, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
14. Barluenga, J.; González, J. M.; Campos, P. J.; Asensio, G. Angew. Chem., Int. Ed. Engl. 1985, 24, 319. Barluenga, J.; Rodríguez, M. A.; Campos, P. J.; Asensio, G. J. Am. Chem. Soc. 1988, 110, 5567. Barluenga, J.; González, J. M.; García-Martin, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
15. Barluenga, J.; Tomás, M.; López-Ortiz, J. F.; Gotor, V. J. Chem. Soc., Perkin Trans. 1 1983, 2273.
16. Barluenga, J.; Jardón, J.; Gotor, V. J. Org. Chem. 1985, 50, 802.
17. Campos, P. J.; Tan, C.-Q.; Rodriguez, M. A. Tetrahedron Lett. 1995, 36, 5257.
18. Hoberg, H.; Barluenga, J. Synthesis 1970, 82 . For a review of alkenimine chemistry see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Aznar, F.; Fustero, S.; Tomás, M. Pure Appl. Chem. 1990, 62, 1957.
19. Hoberg, H.; Barluenga, J. Synthesis 1970, 82 . For a review of alkenimine chemistry see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Aznar, F.; Fustero, S.; Tomás, M. Pure Appl. Chem. 1990, 62, 1957.
20. Hoberg, H.; Barluenga, J. Synthesis 1970, 82 . For a review of alkenimine chemistry see: Barluenga, J. Bull. Soc. Chim. Belg. 1988, 97, 545. Barluenga, J.; Aznar, F.; Fustero, S.; Tomás, M. Pure Appl. Chem. 1990, 62, 1957.
21. Horspool, W.; Armesto, D. Organic Photochemistry: A Comprehensive Treatment; Ellis Horwood: London, 1992; p 457 and references cited therein.
22. Párkányi, C.; Lee, Y. J. Tetrahedron Lett. 1974, 1115.
23. Santamaria, J. In Photoinduced Electron Transfer; Fox, M. A., Chanon, M., Eds.; Elsevier Scientific Publishing Co.: Amsterdam, 1992; Part B, p 483.
24. See, for example: Kropp, P. J.; McNeely, S. A.; Davis, R. D. J. Am. Chem. Soc. 1983, 105, 6907. Davidson, R. S.; Goodin, J. W.; Kemp, G. Adv. Phys. Org. Chem. 1984, 20, 191.
25. See, for example: Kropp, P. J.; McNeely, S. A.; Davis, R. D. J. Am. Chem. Soc. 1983, 105, 6907. Davidson, R. S.; Goodin, J. W.; Kemp, G. Adv. Phys. Org. Chem. 1984, 20, 191.