Mn(OAc)₃-Mediated Selective Free Radical Phosphonylation of Pyridinones and Pyrimidinones

Abstract

The phosphonyl radical generated from the reaction of dimethyl phosphite with manganese(III) acetate adds selectively to the 3-position of pyridin-2-ones or the 5-position of pyrimidin-4-ones to afford phosphonylated products in good yields.

Key words

manganese(III) acetate - phosphonylation - pyridinone - pyrimidinone - dialkyl phosphite - free radical

• References

• 1 Pavlenko NG, Kukhar VP. Ukr. Khim. Zh. (Russ. Ed.) 1982; 48: 395
• 2 Stansfield I, Avolio S, Colarusso S, Gennari N, Narjes F, Pacini B, Ponzi S, Harper S. Bioorg. Med. Chem. Lett. 2004; 14: 5085
• 3 Onysko PP, Golobov YG, Remennikov GY, Cherkasov VM. Zh. Obshch. Khim. 1980; 50: 1230
• 4 Maruyama T, Honjo M. Nucleosides, Nucleotides Nucleic Acids 1988; 7: 203
• 5 Lavilla R, Spada A, Bosch J. Org. Lett. 2000; 2: 1533
• 6 Kagayama T, Nakano A, Sakaguchi S, Ishii Y. Org. Lett. 2006; 8: 407
• 7 Xu W, Zou J.-P, Zhang W. Tetrahedron Lett. 2010; 51: 2639
• 8a Mu X.-J, Zou J.-P, Qian Q.-F, Zhang W. Org. Lett. 2006; 8: 5291
• 8b Zhou P, Jiang Y.-J, Zou J.-P, Zhang W. Synthesis 2012; 44: 1043
• 9a Pan X.-Q, Zou J.-P, Zhang G.-L, Zhang W. Chem. Commun. 2010; 46: 1721
• 9b Pan X.-Q, Wang L, Zou J.-P, Zhang W. Chem. Commun. 2011; 47: 7875

Reviews on P–C bond formation by radical ractions:
• 10a Van der Jeught S, Stevens CV. Chem. Rev. 2009; 109: 2672
• 10b Leca D, Fensterbank L, Lacote E, Malacria M. Chem. Soc. Rev. 2005; 34: 858
• 10c Marque S, Tordo P. Top. Curr. Chem. 2005; 250: 43
• 11 Atwal KS, Rovnyak GC, Schwartz J, Moreland S, Hedberg A, Gougoutas JZ, Malley MF, David MF. J. Med. Chem. 1990; 33: 1510
• 12 Yamaguchi M, Wakasugi K, Saito R, Adachi Y, Yoshikawa Y, Sakurai H, Katoh A. J. Inorg. Biochem. 2006; 100: 260
• 13 Sadanandam YS, Shetty MM, Diwan PV. Eur. J. Med. Chem. 1992; 27: 87
• 14 Wright CM, Chovatiya RJ, Jameson NE, Turner DM, Zhu G, Werner S, Huryn DM, Pipas JM, Day BW, Wipf P, Brodskya JL. Bioorg. Med. Chem. 2008; 16: 3291