Benziporphyrins (e.g. 1), in which one pyrrole unit of the porphyrin framework has been replaced by a meta-disubstituted benzene ring, have been widely investigated. This system shows a wide range of properties and may exist in aromatic or nonaromatic forms. It is of interest to synthesize, characterize, and further investigate the metalation and electronic, magnetic, and spectrophotometric properties of benziporphyrins and related compounds. Benzitripyrrane 2 was generated in two steps from isophthaloyl chloride. Reaction with pyrrole ester 3 in the presence of AlCl3 afforded diketone 4 that was reduced with diborane to form the benzitripyrrane. This key intermediate will be used to prepare new examples of benziporphyrins and related hetero-analogues.

Synthesis of key intermediates for the generation of benziporphyrins

251st National Meeting (2016)

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