Hexamethyldisilazane-promoted sonogashira reaction of polyfunctionalized N-containing heterocycles

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1137-1141

  Inouye, Masahiko ^a   Doi, Yasuhiro ^a   Azuchi, Junichi ^a   Shirato, Wataru ^a   Chiba, Junya ^a   Abe, Hajime ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952766418     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)89     Document Type: Article

References (14)

1. For reviews for Sonogashira reaction, see: K. Sonogashira, 'Metal-catalyzed Cross-coupling Reactions,' ed. by F. Diederich and P. J, Stang, WILEY-VCH, Weinheim, 1998, pp. 203-229;
2. R. Chinchilla and C. Najera, Chem. Rev., 2007, 107, 874.
3. Y. Doi, J. Chiba, T. Morikawa, and M. Inouye, J. Am. Chem. Soc., 2008, 130, 8762.
4. For recent synthetic examples of alkynyl C-nucleosides by Sonogashira reaction, see: (a) T. Bobula, M. Hocek, and M. Kotora, Tetrahedron, 2010, 66, 530
5. (b) M. F. A. Adamo and R. Pergoli, Org. Lett., 2007, 9, 4443
6. (c) D. Heinrich, T. Wagner, and U. Diederichsen, Org. Lett., 2007, 9, 5311. In ref. 3c, a two-step procedure (persilylation of 5-iodocytosine in HMDS and Sonogashira reaction in DIPEA/DMF) was reported.
7. M. Takase, T. Morikawa, H. Abe, and M. Inouye, Org. Lett., 2003, 5, 625.
8. K. Fujimoto, S. Aizawa, I. Oota, J. Chiba, and M. Inouye, Chem. Eur. J., 2010, 16, 2401
9. K. Fujimoto, S. Yamada, and M. Inouye Chem. Commun., 2009, 7164
10. J. Chiba, S. Takeshima, K. Mishima, H. Maeda, Y. Nanai, K. Mizuno, and M. Inouye, Chem. Eur. J., 2007, 13, 8124.
11. HMDS is known to work as a silylating agent with the presence of acidic catalysts: P. G. M. Wuts and T. W. Greene, 'Protective Groups in Organic Synthesis,' A John Wiley & Sons, Inc., Hoboken, 2007, p. 171.
12. For recent examples of persilylation of thiouracil derivatives in HMDS solutions, see: N. A. Al-Awadi, Y. A. Ibrahim, and M. R. Ibrahim, Carbohyd. Res., 2009, 344, 2322.
13. M. Carlucci, E. Kierzek, A. Olejnik, D. H. Turner, and R. Kierzek, Biochemistry, 2009, 48, 10882. See also ref. 3c.
14. +): 630.2580; Found: 630.2598