Approaches to β-fused Porphyrinoporphyrins: Pyrrolo- and Dipyrromethaneporphyrins

✍ Scribed by Claude P. Gros; Laurent Jaquinod; Richard G. Khoury; Marilyn M. Olmstead; Kevin M. Smith

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 278 KB
• Volume: 01
• Category: Article
• ISSN: 1088-4246
• DOI: 10.1002/(sici)1099-1409(199704)1:2<201::aid-jpp25>3.0.co;2-4

✦ Synopsis

10,

15,

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.