Synthesis of 2-aminoazulene derivatives. Nucleophilic and palladium-catalyzed amination of 2-substituted azulene

Tetrahedron

Volumn 59, Issue 41, 2003, Pages 8191-8198

  Yokoyama, Ryuji ^a   Ito, Shunji ^a   Okujima, Tetsuo ^a   Kubo, Takahiro ^a   Yasunami, Masafumi ^b   Tajiri, Akio ^c   Morita, Noboru ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b NIHON UNIVERSITY   (Japan)

^c HIROSAKI UNIVERSITY   (Japan)

Author keywords

2 aminoazulene; 2 bromoazulene; Nucleophilic amination; Palladium catalyzed amination

Indexed keywords

AMINE; AZULENE; AZULENE DERIVATIVE; PALLADIUM; REAGENT;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0141459242     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.08.048     Document Type: Article

References (36)

1. (a) Nozoe T., Matumura S., Murase Y., Seto S. Chem. Ind. 1955;1257
2. (b) Schulze J., Heibronner E. Helv. Chem. Acta. 165:1958;1492-1500
3. (c) Reid D.H., Stafford W.H., Ward J.P. J. Chem. Soc. 1958;1100-1109
4. (d) Nozoe T., Takase K., Tada M. Bull. Chem. Soc. Jpn. 36:1963;1006-1009
5. (e) Zeller K.-P. Azulene. 4th ed. Houben-Weyl; Methoden der Organischen Chemie. Vol. V:1985;Georg Thieme, Stuttgart. Part 2c.
6. Löhr H.-G., Vögtle F. Chem. Ber. 118:1985;905-913.
7. Ito S., Kikuchi S., Morita N., Asao T. J. Org. Chem. 64:1999;5815-5821.
8. (a) Jutz C., Schweiger E. Chem. Ber. 107:1974;2383-2396
9. (b) Abe N. Bull. Chem. Soc. Jpn. 64:1991;2393-2397
10. (c) Nitta M., Akie T., Iino Y. J. Org. Chem. 59:1994;1309-1314
11. (d) Okujima T., Terazono T., Ito S., Morita N., Asao T. Heterocycles. 54:2001;667-678.
12. Herrmann R., Pedersen B., Wagner G., Youn J.-H. J. Organomet. Chem. 571:1998;261-266.
13. Tilney-Bassett J.F., Waters W.A. J. Chem. Soc. 1959;3123-3129.
14. (a) Hafner K., Weldes H. Liebigs Ann. Chem. 606:1957;90-99
15. (b) Hafner K., Patzelt H., Kaiser H. Liebigs Ann. Chem. 656:1962;24-33
16. (c) McDonald R.N., Petty H.E., Wolfe N.L., Paukstelis J.V. J. Org. Chem. 39:1974;1877-1886
17. (d) Morita T., Fujita T., Takase K. Bull. Chem. Soc. Jpn. 53:1980;1647-1651
18. (e) Nozoe T., Takase K., Tada M. Bull. Chem. Soc. Jpn. 38:1965;247-251
19. (f) Tada M. Bull. Chem. Soc. Jpn. 39:1966;1954-1961
20. (g) McDonald R.N., Richmond J.M., Curtis J.R., Petty H.E., Hoskins T.L. J. Org. Chem. 41:1976;1811
21. (h) Hünig S., Hafner K., Ort B., Müller M. Liebigs Ann. Chem. 1986;1222-1240
22. (i) Makosza M., Podraza R. Eur. J. Org. Chem. 2000;193-198.
23. (a) Nozoe, T.; Seto, S.; Matsumura, S. Bull. Chem. Soc. Jpn 1962, 35 1990-1998.
24. (a) Nozoe, T.; Seto, S.; Matsumura, S. Bull. Chem. Soc. Jpn 1962, 35 1990-1998. (b) McDonald R.N., Richmond J.M. J. Org. Chem. Soc. 40:1975;1689-1694.
25. (a) Wolfe J.P., Buchwald S.L. J. Org. Chem. 62:1997;1264-1267
26. (b) Louie J., Driver M.S., Hamann B.C., Hartwig J.F. J. Org. Chem. 62:1997;1268-1273
27. (c) Hartwig J.F. Angew. Chem. Int. Ed. 37:1998;2046-2067
28. (d) Wolfe J.P., Wagaw S., Marcous J.-F., Buchwald S.T. Acc. Chem. Res. 31:1998;805-815
29. (e) Grasa G.A., Viciu M.S., Huang J., Nolan S.P. J. Org. Chem. 66:2001;7729-7737.
30. Ito S., Yokoyama R., Okujima T., Terazono T., Kubo T., Tajiri A., Watanabe M., Morita N. Org. Biomol. Chem. 1:2003;1947-1952.
31. Yokoyama R., Ito S., Watanabe M., Harada N., Kabuto C., Morita N. J. Chem. Soc., Perkin Trans. 1. 2001;2257-2261.
32. Ito S., Nomura A., Morita N., Kabuto C., Kobayashi H., Maejima S., Fujimori K., Yasunami M. J. Org. Chem. 67:2002;7295-7302.
33. Takase K., Asao T., Takagi Y., Nozoe T. Chem. Commun. 1968;368-370.
34. Master's Thesis of Kikuchi, M., Tohoku University, 1980.
35. (b) Nitta M., Takayasu T.J. J. Chem. Soc., Perkin Trans. 1. 1998;1325-1333.
36. Replogle L.L., Maynard J.R. J. Org. Chem. 32:1967;1909-1915.