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 journalArticle

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

Fingerprint Dive into the research topics of 'Multigram synthesis of a water-soluble porphyrazine and derived seco-porphyrazine labeling agents'. Together they form a unique fingerprint.

  • Cite this

    Guinchard, X., Fuchter, M. J., Ruggiero, A., Duckworth, B. J., Barrett, A. G. M., & Hoffman, B. M. (2007). Multigram synthesis of a water-soluble porphyrazine and derived seco-porphyrazine labeling agents. Organic Letters, 9(25), 5291-5294. https://doi.org/10.1021/ol702481x