Synthesis of Substituted Imidazo[1, 5-a]pyrimidines, 1H-pyrrolo[2, 3-b]pyridines and 3-methyl-3H-imidazo[4, 5-b]pyridines

Letters in Organic Chemistry

Volumn 6, Issue 3, 2009, Pages 203-207

  Wu, Jingshing ^a   Xing, Xuechao ^a   Cuny, Gregory D ^a  

^a BRIGHAM AND WOMEN S HOSPITAL   (United States)

Author keywords

1H pyrrolo 2, 3 b pyridines; 3 methyl 3H imidazo 4, 5 b pyridines; 7 azaindoles; Cyclization; Imidazo 1, 5 a pyrimidines

Indexed keywords

EID: 69249229769     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017809787893000     Document Type: Article

References (18)

1. Yu, P.B.; Hong, C.C.; Sachidanandan, C.; Babitt, J.L.; Deng, D.Y.; Hoyng, S.A.; Lin, H.Y.; Bloch, K.D.; Peterson, R.T. Nat. Chem. Biol., 2008, 4, 33.
2. Ross, S.; Hill, C.S. Int. J. Biochem. Cell Biol., 2008, 40, 383.
3. Cuny, G.D.; Yu, P.B.; Laha, J.K.; Xing, X.; Liu, J.-F.; Lai, C.S.; Deng, D.Y.; Sachidanandan, C.; Bloch, K.D.; Peterson, R.T. Bioorg. Med. Chem. Lett., 2008, 18, 4388.
4. Hajos, G.; Riedl, Z. Sci. Synth., 2002, 12, 613.
5. Merour, J.-Y.; Joseph, B. Curr. Org. Chem., 2001, 5, 471;
6. Popowycz, F.; Routier, S.; Joseph, B.; Merour, J.-Y. Tetrahedron, 2006, 63, 1031.
7. Yutilov, Y.M. Adv. Heterocycl. Chem., 2005, 89, 169.
8. For other examples of similar cyclizations see: Chern, J.-W.; Lee, C.-C.; Lin, S.-L.; Tung, C.-S. Chin. Pharm. J., 1996, 48, 37.
9. Novinson, T.; O'Brien, D.E.; Robins, R.K. J. Heterocycl. Chem., 1974, 11, 873.
10. Chiai, E.; Sibata, M. Yakugaku Zasshi, 1939, 59, 185.
11. +, calcd 298.1181.
12. For other examples of similar cyclizations see: (a) Wesch, T.; Iaroshenko, V.O.; Groth, U. Synlett, 2008, 1459.
13. Semichenko, E.S.; Root, E.V.; Pokrovskii, L.M.; Suboch, G.A. Russ. J. Org. Chem., 43, 406.
14. Kurihara, T.; Tani, T.; Imai, H.; Nasu, K. Chem. Pharm. Bull., 1980, 28, 2972.
15. +, calcd 283.1073
16. For an examples of similar cyclizations see: Blache, Y.; Gueiffier, A.; Chavignon, O.; Viols, H.; Teulade, J.C.; Chapat, J.P. Heterocycles, 1994, 38, 1527.
17. Zimmermann, H.; Brueckner, D.; Henninger, K.; Rosentreter, U.; Hendrix, M.; Heldenich, J.; Lang, D.; Radtke, M.; Paulsen, D.; Kern, A. WO2006089664, 2006.
18. +, calcd 353.1392.