Direct Amination of meso‐Tetraarylporphyrin Derivatives – Easy Route to A3B‐, A2BC‐, and A2B2‐Type Porphyrins Bearing Two Nitrogen‐Containing Substituents at the meso‐Positioned Phenyl Groups |
| |
Authors: | Stanis?aw Ostrowski Sebastian Grzyb Agnieszka Mikus |
| |
Institution: | Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, PL‐08‐110 Siedlce, (fax: +48‐25‐644‐2045) |
| |
Abstract: | meso‐Tetraarylporphyrinato complexes 1a – g (ZnII, CuII, and NiII) bearing one or two nitro‐substituted aryl moieties react with 1,1,1‐trimethylhydrazinium iodide in the presence of tBuOK in THF at 0–5° or in the presence of KOH in DMSO at 60–70° according to a nucleophilic substitution of an H‐atom, thus affording porphyrins 2a – g and 3f , g with amino‐functionalized meso‐positioned aryl substituents in yields up to 73% (Scheme 1 and Table). The products obtained are attractive intermediates for further derivatization of porphyrins and may be of potential use as sensitizers in photodynamic cancer therapy. |
| |
Keywords: | Porphyrins Amination Nucleophilic substitutions Zink complexes Copper complexes Nickel complexes |
|
|