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Synlett 1994; 1994(11): 909-910
DOI: 10.1055/s-1994-23044
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Synthesis of a Porphyrin with Fused Five- and Seven-membered Exocyclic Rings from a Cross-conjugated Tetracyclic Dipyrrole

Zao Hu* , Timothy D. Lash
  • *Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, USA
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Publication Date:
22 March 2002 (online)

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1-Aza-7-pyrrolylmethyl-1,4,5,6-tetrahydroazulene 1 was cyclized with 3.5% HBr-AcOH to give a cross-conjugated dipyrrole 3 in good yield; hydrogenation of the double bond gave the tetracyclic dipyrrole 5 and subsequent hydrogenolysis of the benzyl esters, followed by acid catalyzed condensation with diformyldipyrrylmethane 7 gave a porphyrin 8 bearing two fused exocyclic rings.