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■ Synthesis of a Difuryl Analog of the Oxophlorins

Timothy D. Lash and Yanet G. Motta

*Faculty of Chemistry, Northern State College, Aberdeen, South Dakota 57401, U.S.A.

Abstract

Condensation of 2,2’-bis(5-formylfuryl)methanone with a 2,2’-dipyrrylmethane-5,5’-dicarboxylic acid in trifluoroacetic acid afforded a macrocycle (6) analogous to the oxophlorin (oxyporphyrin) system. IR and UV spectra indicate that this compound exists as the keto tautomer (6) rather than the fully conjugated enol form (7a). (6) did not react with acetic anhydride-pyridine and the enol acetate (7b) could not be isolated, although the diperchlorate salt was formed under acidic conditions.