Quatyrin is the hypothetical hydrocarbon analogue of the porphyrins (Lash, T. D. et al. Chem. Commun. 1999  , 819-820). To date, no syntheses of this theoretically important system have been reported, although numerous examples of mono- and dicarbaporphyrins are known. A new approach to tetracarbaporphyrinoid systems has been developed with the goal of synthesizing substituted quatyrins. Fulvene aldehyde 1  was prepared by reacting 6-tert-butylazulene-1-carbaldehyde with an indene-derived enamine in the presence of dibutylboron triflate. Luche reduction with NaBH4/CeCl3 then gave the related carbinol 2  , which self-condensed in the presence of boron trifluoride etherate to afford the novel porphyrinoid macrocycle 3  . This system, which is not fully conjugated, contains the same carbon skeleton as quatyrin. Investigations into the oxidation of 3  to produce fully conjugated structures are underway.

Synthesis of a dihydrotetracarbaporphyrin

246th National Meeting (2013)

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