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Paper | Special issue | Vol 77, No. 1, 2009, pp.301-309
Published online, 2nd June, 2008
DOI: 10.3987/COM-08-S(F)15
Preparation of a Building Block for a Pyrazole Expanded Porphyrin and Isolation of a Tripyrrolyl Ketone Decomposition Product

Alfred Hassner* and Eran Fogler

*Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel


Dipyrrolylpyrazole 3, obtained from 1,3-di-(1H-pyrrol-2-yl)propane-1,3-dione (2), was prepared as a building block for pyrazole-based binuclear expanded porphyrins. An unusual transformation of 2, in solution or on chromatography, afforded 1,3,3-tri-(1H-pyrrol-2-yl)prop-2-en-1-one (4) in good yield. HRMS indicated the presence of an unstable pyrazole-based expanded porphyrin 1 and its trinuclear Mg derivative 5 on condensation of 3 with benzaldehyde.