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meso-Substituted Dipyrromethanes from Vinylogous Aromatic Heterocycles and Their Utilization to the Synthesis of meso-Functionalized Porphyrins

Hong, Seong-Jin    (Institute of Basic Science and Department of Chemistry, Kangwon National University   ); Lee, Mi-Hye    (Institute of Basic Science and Department of Chemistry, Kangwon National University   ); Lee, Chang-Hee    (Institute of Basic Science and Department of Chemistry, Kangwon National University  );
  • 초록

    meso-Functionalized dipyrromethanes 6-10 were synthesized by acid-catalyzed addition of pyrrole to ${\alpha}$ -position of 2-alkenyl pyrroles. The regiochemistry of the reaction can be explained by either the formation of more stable carbocation intermediate or ${\beta}$ -addition of ${\alpha},{\beta}$ -unsaturated carbonyl compounds. The starting 2-alkenyl pyrroles were synthesized by Aldol condensation of 2-formylpyrrole with active methylene compounds such as nitromethane, diethylmalonate and malononitrile. Attempted '2+2' condensation of meso-diethylmalonyldipyrromethane, meso-(p-tolyl)dipyrromethane and p-tolualdehyde afforded three different porphyrins 12, 13 and 14 in reasonable yields. On the other hand, meso-(nitromethyl)dipyrromethane with p-(tbutyl) benzaldehyde resulted in the formation of three different porphyrins such as 5,15-dicyano-10,20-diarylporphyrin (16), 5-cyano-15-formyl-10,20-diarylporphyrin (17) and 5,15-diformyl-10,20-diarylporphyrin (18) in low yields. Conversion of nitromethyl groups to nitrile and (or) formyl group was observed under the porphyrin forming conditions.


  • 주제어

    meso-(Diethylmalonyl)-dipyrromethanes .   Vinylpyrroles .   5,15-Dicyano-10,20-diarylporphyrin .   5-Cyano-15-formyl-10,20-diarylporphyrin.  

  • 참고문헌 (22)

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 저자의 다른 논문

  • Hong, Seong-Jin (3)

    1. 2003 "Novel Synthesis of Phlorin Derivatives and Their Anion Binding Properties" Bulletin of the Korean Chemical Society 24 (5): 661~663    
    2. 2006 "Synthesis and Structure of Non-aromatic Porphyrinoid Schiff-base Macrocycles Bearing Thiophene" Bulletin of the Korean Chemical Society 27 (6): 925~928    
    3. 2008 "Synthesis of Porphyrins Bearing Multiple meso-Aminoalkyl Groups" Bulletin of the Korean Chemical Society 29 (3): 693~696    
  • Lee, Chang-Hee (15)

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