Azuliporphyrins 1 are carbaporphyrinoids structures that have been widely studied due to their intriguing spectroscopic and chemical properties. In this project, the effect of introducing alkyl substituents into the macrocyclic cavity is under investigation. 2-Methylazulene (2) has been prepared in three steps from tropolone p-toluenesulfonate and ethyl acetoacetate. Reaction of 2 with an acetoxymethylpyrrole 3 in the presence of K-10 Montmorillonite clay then gave azulitripyrrane 4 in 75% yield. Currently, the conversion of 4 into azuliporphyrin derivatives such as 5 is under review.

Synthesis of azuliporphyrins from 2-methylazulene

255th National Meeting (2018)

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