Synthesis and Reactions of Aminoporphyrazines with Annulated Five- and Seven-Membered Rings Academic Article uri icon

abstract

  • The novel five- and seven-membered ring appended aminoporphyrazines 3 and 12 have been prepared via mixed Linstead macrocyclization. The structures of both have been unequivocally established by X-ray crystallographic studies. Reductive deselenation of selenadiazole 3 in the presence of 9,10-phenanthrenequinone or 2,3-butanedione results in the formation of pyrazines 6a,b, whereas oxidation of porphyrazine 12 gave the corresponding seco derivative 14. seco-Porphyrazine 14 mediates the generation of singlet oxygen with a quantum yield of 0.74.

author list (cited authors)

  • Baum, S. M., Trabanco, A. A., Montalban, A. G., Micallef, A. S., Zhong, C., Meunier, H. G., ... Hoffman, B. M.

publication date

  • January 1, 2003 11:11 AM