Pd(OAc)2 catalyzed synthesis of heteroaryl-substituted 1,8-naphthyridine derivatives via C-N-coupling reactions of chloronaphthyridines

Chinese Chemical Letters

Volumn 18, Issue 4, 2007, Pages 383-386

  Jin, Shou Wen ^a   Liu, Bin ^a   Chen, Wan Zhi ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

C N coupling reaction; Catalyst; Naphthyridine; Palladium

Indexed keywords

EID: 33947601945     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2007.01.024     Document Type: Article

References (13)

1. Goswami S., and Mukherjee R. Tetrahedron Lett. 38 (1997) 1619
2. Nakatani K., Sando S., and Saito I. J. Am. Chem. Soc. 122 (2000) 2172
3. Gavrilova A.L., and Bosnich B. Chem. Rev. 104 (2004) 349
4. Guram A.S., Rennels R.A., and Buchwald S.L. Angew. Chem., Int. Ed. Engl. 34 (1995) 1348
5. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046
6. Sun X.J., Yu Z.K., Wu S.Z., and Xiao W.J. Organometallics 24 (2005) 2959
7. Ligthart G.B.W.L., Ohkawa H., Sijbesma R.P., and Meijer E.W. J. Org. Chem. 71 (2006) 375
8. Ligthart G.B.W.L., Ohkawa H., Sijbesma R.P., and Meijer E.W. J. Am. Chem. Soc. 127 (2005) 810
9. Newkome G.R., Garbis S.J., Majestic V.K., et al. J. Org. Chem. 46 (1981) 833
10. Mangini A., and Colonna M. Gazz. Chim. Ital. LXXIII (1943) 323
11. 3/Pd = 2.0), inorganic base (1 equiv), imine (2.2 equiv), and 1,4-dioxane (10 mL). The Schlenk tube was evacuated, and back-filled with Ar three times. The mixture was allowed to react at 120 °C. After stirring for 48 h, the mixture was cooled, filtered over celite, and evaporated in vacuo to dryness. The residue was washed with water, filtered and dissolved in 25% hydrochloride. The pH of filtrate was adjusted to 7-8 to afford the products, which was dried in vacuo, and recrystallized from ethanol.
12. int = 0.0406), R1, w R 2 (I > 2σ(I)): 0.0759, 0.1764. CCDC no. 610949.
13. The analytical data of compounds 3-10 were submitted to the editorial office of CCL.