Palladium-catalyzed amination of 2-chloro-1-azaazulene with 2-aminopyridine

Heterocycles

Volumn 83, Issue 3, 2011, Pages 547-554

  Oda, Mitsunori ^a   Miyawaki, Daisuke ^a   Matsumoto, Naoko ^b   Kurodab, Shigeyasu ^b  

^a SHINSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952272414     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-12109     Document Type: Article

References (19)

1. For palladium-catalyzed aminations, see following reviews
2. J. P. Wolfe, S. Wagaw, J.-F. Marcoux, and S. L. Buchwald, Acc. Chem. Res., 1998, 31, 805
3. J. F. Hartwig, Acc. Chem. Res., 1998, 31, 852;
4. J. F. Hartwig, Angew. Chem. Int. Ed., 1998, 37, 2046.
5. K. Koizumi, K. Shimabara, A. Takemoto, S. Yamazaki, N. Yamauchi, H. Fujii, M. Kurosawa, T. Konakahara, and N. Abe, Heterocycles, 2009, 79, 319.
6. I. B. Campbell, "Organocopper Reagents", ed. by R. J. K. Taylor, Oxford University Press, Oxford, 1994, ch. 10, pp. 217-235.
7. M. Oda, K. Ogura, G. Chung Thanh, S. Kishi, S. Kuroda, K. Fujimori, T. Noda, and N. Abe, Tetrahedron Lett., 2007, 48, 4471.
8. N. Abe, E. Hashimoto, H. Fujii, Y. Murakami, S. Tagashira, and A. Kakehi, Heterocycles, 2004, 63, 2341.
9. N. Abe, M. Tanaka, T. Maeda, H. Fujii, and A. Kakehi, Heterocycles, 2005, 66, 229.
10. T. Ariyoshi, T. Noda, S. Watarai, S. Tagashira, Y. Murakami, H. Fujii, and N. Abe, Heterocycles, 2009, 77, 565.
11. Compound 4 has been synthesized as a deesterified by-product in the reaction of Scheme 1 with 2-aminopyridine. However, its detail of spectroscopic properties is not reported yet. See ref. 2.
12. For trivial names and references of reagents, see followings. XPhos is a trivial name of 2-dicyclohexylphosphino- 2',4',6'-triisopropylbiphenyl
13. X. Huang, K. W. Anderson, D. Zim, L. Jiang, A. Klapars, and S. L. Buchwald, J. Am. Chem. Soc., 2003, 125, 6653. QPhos is a trivial name of 1, 2, 3, 4, 5-pentaphenyl-1#-(di-tert-butylphosphino)ferrocene
14. Q. Shelby, N. Kataoka, G. Mann, and J. F. Hartwig, J. Am. Chem. Soc., 2000, 122, 10718. Dppf is 1,1#-bis(diphenylphosphino)-ferrocene
15. G. Marr and T. Hunt, J. Chem. Soc., C, 1969, 7, 1070. Dba is dibenzalacetone. TrippyPhos is a trivial name of 1-{2-(di-tert-butylphosphino) phenyl}-3,5-diphenyl-1H-pyrazole
16. R. A. Singer, S. Caron, R. E. McDermott, P. Arpin, and M. D. Nga, Synthesis, 2003, 1727. XantPhos is a trivial name of 4,5-bis(diphenylphosphino)- 9,9#-dimethylxanthene
17. S. Hillebrand, J. Bruckmann, C. Kriiger, and M. W. Haenel, Tetrahedron Lett., 1995, 36, 75. BINAP is 1,1'-bi{(2-diphenylphosphino) naphthyl}.
18. M. R. Netherton and G. C. Fu, Org. Lett., 2001, 3, 4295.
19. T. Nozoe, S. Seto, S. Matsuura, and T. Terasawa, Chem. Ind., 1954, 1357.