Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
 
An Approach to Pyrazoline-Fused Chlorins by Dipolar [3 + 2]-Cycloaddition of Iminonitriles to meso-Tetrakis(pentafluorophenyl)porphyrin: Synthesis of New PDT Photosensitizers
Przemysław WyrebekStanisław Ostrowski
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2012 Volume 85 Issue 10 Pages 1167-1174

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Abstract

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).

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© 2012 The Chemical Society of Japan
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