A facile and regioselective synthesis of trans-heterofunctionalized porphyrazine derivatives

Timothy P. Forsyth, D. Bradley G Williams, Antonio Garrido Montalban, Charlotte L. Stern, Anthony G.M. Barrett, Brian M. Hoffman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

Abstract

New methodology was developed for the selective synthesis of regiochemically defined porphyrazines of the form M[pz(A2;B2)] (shown in Chart 1) where A and B represent peripheral functionalization attached to the β-positions of the pyrroles. Specifically, phthalonitriles or derivatives thereof with sterically bulky groups in positions 3 and 6, in particular 4,7- bis(isopropyloxy)-1,3-diiminoisoindoline (3) act as a 'trans director' when macrocyclized with heteroatom-appended maleonitriles under Linstead conditions, the result being preferential formation of the trans- M[pz(A2;B2)] pigment where A = SR, NMe2, OR, as well as R (shown in Chart 2). Linstead crossover macrocyclization of 3 with 4, 11, 15, and 18 gave pigments 10, 14, 17, and 19, respectively. These pigments were characterized by 1H NMR, 13C NMR, UV-visible spectroscopy, mass spectrometry, microanalysis, and 17 was characterized by single-crystal X-ray analysis.

Original languageEnglish (US)
Pages (from-to)331-336
Number of pages6
JournalJournal of Organic Chemistry
Volume63
Issue number2
DOIs
StatePublished - Jan 23 1998

ASJC Scopus subject areas

  • Organic Chemistry

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