Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings.
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.
Baum
Sven M
SM
Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London SW7 2AY, UK.
Trabanco
Andrés A
AA
Montalban
Antonio Garrido
AG
Micallef
Aaron S
AS
Zhong
Chang
C
Meunier
Hubert G
HG
Suhling
Klaus
K
Phillips
David
D
White
Andrew J P
AJ
Williams
David J
DJ
Barrett
Anthony G M
AG
Hoffman
Brian M
BM