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

doi:10.1021/ol702481x

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

Chemistry

Research output: Contribution to journal › Article › peer-review

15 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 language	English (US)
Pages (from-to)	5291-5294
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	25
DOIs	https://doi.org/10.1021/ol702481x
State	Published - Dec 6 2007

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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T1 - Multigram synthesis of a water-soluble porphyrazine and derived seco-porphyrazine labeling agents

AU - Guinchard, Xavier

AU - Fuchter, Matthew J.

AU - Ruggiero, Andrea

AU - Duckworth, Brian J.

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M.

PY - 2007/12/6

Y1 - 2007/12/6

N2 - (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.

AB - (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.

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

Abstract

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