Approaches to β-fused porphyrinoporphyrins: Pyrrolo and dipyrromethanoporphyrins
Reaction of (2-nitro-5,10,15,20-tetraphenylporphyrinato)nickel(II) 3 or its copper(II) complex 4 with α-isocyanoacetic esters in the presence of 1,8-diazabicyclo[5.4.O]undec-7-ene accomplishes the first syntheses of β-fused pyrroloporphyrins (e.g. 5-10). The removal of the fused pyrrole ester protecting groups to give the di-α-free pyrroloporphyrins 2a and 13 is described, as well as some pyrrole-type chemistry. Unsymmetrical fused dipyrromethanoporphyrins (16-18) were synthesized by reacting 5-acetoxymethylpyrrole-2-carboxylates (14,15) with mono-α-free pyrroloporphyrins (5-8) in the presence of Montmorillonite clay. A symmetrical bis-porphyrinyl dipyrromethane 19 was also prepared by condensation of the β-fused methyl ester pyrroloporphyrin 7 with dimethoxymethane in ethanol and concentrated hydrochloric acid. © 1997 by John Wiley & Sons, Ltd.
Publication Source (Journal or Book title)
Journal of Porphyrins and Phthalocyanines
Gros, C., Jaquinod, L., Khoury, R., Olmstead, M., & Smith, K. (1997). Approaches to β-fused porphyrinoporphyrins: Pyrrolo and dipyrromethanoporphyrins. Journal of Porphyrins and Phthalocyanines, 1 (2), 201-212. https://doi.org/10.1002/(SICI)1099-1409(199704)1:2<201::AID-JPP25>3.3.CO;2-W