An Approach to Pyrazoline-Fused Chlorins by Dipolar [3 + 2]-Cycloaddition of Iminonitriles to meso-Tetrakis(pentafluorophenyl)porphyrin

meso-Tetrakis(pentafluorophenyl)porphyrin reacts at higher temperature with unstable iminonitriles (R-C≡N+-N--Ar), affording pyrazoline-fused chlorins, according to dipolar [3 + 2]-cycloaddition pathway. The respective iminonitriles were in situ generated from the corresponding functionalized α-halo...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2012-10, Vol.85 (10), p.1167
Main Authors: Wyrebek, Przemyslaw, Ostrowski, Stanislaw
Format: Article
Language:English
Online Access:Get full text
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Summary:meso-Tetrakis(pentafluorophenyl)porphyrin reacts at higher temperature with unstable iminonitriles (R-C≡N+-N--Ar), affording pyrazoline-fused chlorins, according to dipolar [3 + 2]-cycloaddition pathway. The respective iminonitriles were in situ generated from the corresponding functionalized α-halogenohydrazine derivatives by 1,3-elimination of HX in the presence of base (NEt3, DABCO). This method allows synthesis of very attractive moieties which may be of potential use as sensitizers in photodynamic therapy (PDT).
ISSN:0009-2673
1348-0634