Carbaporphyrinoid systems have been widely investigated due to their intriguing aromatic characteristics, unusual reactivity, and ability to form stable organometallic derivatives. In this project, a new approach to heterocarbaporphyrins has been developed. Base-catalyzed reaction of technical grade indene with pyrrole-2-carboxaldehyde produced the corresponding fulvene 1. Reduction of 1 with LiAlH4 gave a dihydrofulvene, and further reaction with furfural or thiophene-2-carboxaldehyde afforded the carbatripyrrin intermediates 2 and 3. Carbatripyrrin 2 reacted with aromatic dialdehydes to yield carbaporphyrinoid systems. In addition, condensation of 2 with aromatic dicarbinols gave a series of heterocarbaporphyrins 4. Using this methodology, the first examples of porphyrin analogues with four different atoms within the macrocyclic cavity have been synthesized.

Synthesis of heterocarbaporphyrins from carbatripyrrin intermediates

253rd National Meeting (2017)

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