A simple synthetic method for 3-trifluoroacetylated 4-aminoquinolines from 4-dimethylaminoquinoline by novel trifluoroacetylation and N-N exchange reactions

Chemistry Letters

Volumn , Issue 1, 2000, Pages 50-51

  Okada, Etsuji ^a   Sakaemura, Takushi ^a   Shimomura, Naofumi ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034340836     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.50     Document Type: Article

References (23)

1. L. H. Miller, M. F. Good, and G. Milon, Science, 264, 1878 (1994).
2. D. J. Krogstad, I. Y. Gluzman, D. E. Kyle, A. M. J. Oduola, S. K. Martin, W. K. Milhous, and P. H. Schlesinger, Science, 238, 1283 (1987); D. De. J. T. Mague, L. D. Byers, and D. J. Krogstad, Tetrahedron Lett., 36, 205 (1995).
3. D. J. Krogstad, I. Y. Gluzman, D. E. Kyle, A. M. J. Oduola, S. K. Martin, W. K. Milhous, and P. H. Schlesinger, Science, 238, 1283 (1987); D. De. J. T. Mague, L. D. Byers, and D. J. Krogstad, Tetrahedron Lett., 36, 205 (1995).
4. For recent examples: P. M. O'Neill, P. G. Bray, S. R. Hawley, S. A. Ward, and B. K. Park, Pharmacol. Ther. , 77. 29 (1998): D. De, F. M. Krogstad, L. D. Byers, and D. J. Krogstad, J. Med. Chem., 41, 4918 (1998); T. O. Nguyen, J. D. Capra, and R. D. Sontheimer, Lupus, 7, 148 (1998); D. De, L. D. Byers, and D. J. Krogstad, J. Heterocycl. Chem., 34, 315 (1997).
5. For recent examples: P. M. O'Neill, P. G. Bray, S. R. Hawley, S. A. Ward, and B. K. Park, Pharmacol. Ther. , 77. 29 (1998): D. De, F. M. Krogstad, L. D. Byers, and D. J. Krogstad, J. Med. Chem., 41, 4918 (1998); T. O. Nguyen, J. D. Capra, and R. D. Sontheimer, Lupus, 7, 148 (1998); D. De, L. D. Byers, and D. J. Krogstad, J. Heterocycl. Chem., 34, 315 (1997).
6. For recent examples: P. M. O'Neill, P. G. Bray, S. R. Hawley, S. A. Ward, and B. K. Park, Pharmacol. Ther. , 77. 29 (1998): D. De, F. M. Krogstad, L. D. Byers, and D. J. Krogstad, J. Med. Chem., 41, 4918 (1998); T. O. Nguyen, J. D. Capra, and R. D. Sontheimer, Lupus, 7, 148 (1998); D. De, L. D. Byers, and D. J. Krogstad, J. Heterocycl. Chem., 34, 315 (1997).
7. For recent examples: P. M. O'Neill, P. G. Bray, S. R. Hawley, S. A. Ward, and B. K. Park, Pharmacol. Ther. , 77. 29 (1998): D. De, F. M. Krogstad, L. D. Byers, and D. J. Krogstad, J. Med. Chem., 41, 4918 (1998); T. O. Nguyen, J. D. Capra, and R. D. Sontheimer, Lupus, 7, 148 (1998); D. De, L. D. Byers, and D. J. Krogstad, J. Heterocycl. Chem., 34, 315 (1997).
8. R. Filler and S. M. Naqvi, in "Biomedicinal Aspects of Fluorine Chemistry," ed by R. Filler and Y. Kobayashi, Kodansha & Elsevier Biomedical, Tokyo (1982), Chap. 1, p. 1; J. T. Welch, Tetrahedron, 43, 3123 (1987).
9. R. Filler and S. M. Naqvi, in "Biomedicinal Aspects of Fluorine Chemistry," ed by R. Filler and Y. Kobayashi, Kodansha & Elsevier Biomedical, Tokyo (1982), Chap. 1, p. 1; J. T. Welch, Tetrahedron, 43, 3123 (1987).
10. M. Hojo, R. Masuda, and E. Okada, Tetrahedron Lett., 28, 6199 (1987); M. Hojo, R. Masuda, E. Okada, and H. Miya, Synthesis. 1989, 870; E. Okada, N. Tsukushi, Y. Otsuki, S. Nishiyama, and T. Fukuda, Synlett, 1999, 126; E. Okada and N. Tsukushi, Synlett, 1999, 210.
11. M. Hojo, R. Masuda, and E. Okada, Tetrahedron Lett., 28, 6199 (1987); M. Hojo, R. Masuda, E. Okada, and H. Miya, Synthesis. 1989, 870; E. Okada, N. Tsukushi, Y. Otsuki, S. Nishiyama, and T. Fukuda, Synlett, 1999, 126; E. Okada and N. Tsukushi, Synlett, 1999, 210.
12. M. Hojo, R. Masuda, and E. Okada, Tetrahedron Lett., 28, 6199 (1987); M. Hojo, R. Masuda, E. Okada, and H. Miya, Synthesis. 1989, 870; E. Okada, N. Tsukushi, Y. Otsuki, S. Nishiyama, and T. Fukuda, Synlett, 1999, 126; E. Okada and N. Tsukushi, Synlett, 1999, 210.
13. M. Hojo, R. Masuda, and E. Okada, Tetrahedron Lett., 28, 6199 (1987); M. Hojo, R. Masuda, E. Okada, and H. Miya, Synthesis. 1989, 870; E. Okada, N. Tsukushi, Y. Otsuki, S. Nishiyama, and T. Fukuda, Synlett, 1999, 126; E. Okada and N. Tsukushi, Synlett, 1999, 210.
14. F. Palacios, D. Aparicio, and J. Garcia, Tetrahedron, 54, 1647 (1998).
15. J. March, in "Advanced Organic Chemistry." 4th ed. Wiley-Interscience, New York (1992), Chap. 11 . p. 540; J. F. Begue and D. Bonnet-Delpon, Tetrahedron, 47, 3207 (1991).
16. J. March, in "Advanced Organic Chemistry." 4th ed. Wiley-Interscience, New York (1992), Chap. 11 . p. 540; J. F. Begue and D. Bonnet-Delpon, Tetrahedron, 47, 3207 (1991).
17. T. L. Gilchrist, in "Heterocyclic Chemistry." Pitman, London (1985), Chap. 8. p.276; D. L. Comins and S. O'Connor, Adv. Heterocycl. Chem., 44, 199 (1988).
18. T. L. Gilchrist, in "Heterocyclic Chemistry." Pitman, London (1985), Chap. 8. p.276; D. L. Comins and S. O'Connor, Adv. Heterocycl. Chem., 44, 199 (1988).
19. G. Simehen and A. Schmidt, Synthesis, 1996, 1093.
20. 2O: C, 58.21: H, 4.13; N, 10.44%. Found: C, 58.27; H, 4.31: N, 10.20%.
21. 2O: C, 49.55; H, 4.16; N, 12.84%. Found: C, 49.64; H, 4.13; N, 12.78%.
22. 2O: C, 65.45; H, 3.97; N, 8.48%. Found: C, 65.37; H, 4.19; N, 8.33%.
23. For example, the reaction of 5 with henzylamine (3 eq) in refluxing valeronitrile for 48 h did not take place and almost all of substrate 5 was recovered.