Multigram synthesis of a water-soluble porphyrazine and derived seco-porphyrazine labeling agents

Xavier Guinchard, Matthew J. Fuchter, Andrea Ruggiero, Brian J. Duckworth, Anthony G.M. Barrett*, Brian M. Hoffman

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

(Chemical Equation Presented) Porphyrazine III has been synthesized on a large scale (18.4 g), with minimal chromatographic purification by employing a novel one-pot, 3-step sequence. Two dinitrile precursors I and II, the latter of which consisted of a mixture of geometric isomers, were transformed, via the corresponding pyrroline diimines, into a mixture of III and the octa-Ar 1-porphyrazine. Isolated macrocycle III was subsequently transformed into IV, a water-soluble seco-porphyrazine suitable for the labeling of biological vectors.

Original languageEnglish (US)
Pages (from-to)5291-5294
Number of pages4
JournalOrganic Letters
Volume9
Issue number25
DOIs
StatePublished - Dec 6 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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