Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

Sven M. Baum, Andrés A. Trabanco, Antonio Garrido Montalban, Aaron S. Micallef, Chang Zhong, Hubert G. Meunier, Klaus Suhling, David Phillips, Andrew J.P. White, David J. Williams, Anthony G.M. Barrett*, Brian M. Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

77 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1665-1670
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number5
DOIs
StatePublished - Mar 7 2003

ASJC Scopus subject areas

  • Organic Chemistry

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