Synthesis of Alkyl Substituted Carbatripyrrins and Their Application to the Preparation of Carbaporphyrins and Oxacarbaporphyrins.

ABSTRACT: Unsubstituted carbatripyrrins have previously been shown to be useful intermediates in the synthesis of benzocarbaporphyrins and related core-modified analogues. However, the absence of substituents often resulted in the formation of poorly soluble products. In this study, four examples alkyl substituted carbatripyrrins were constructed by base-catalyzed condensation of dihydrofulvenes with pyrrole aldehydes. Further reaction with a pyrrole dialdehyde in the presence of trifluoroacetic acid afforded a series of carbaporphyrins, while reactions with 2,5-furandicarboxaldehyde generated oxacarbaporphyrins. These results demonstrate that alkyl substituted carbatripyrrins are promising precursors to new carbaporphyrinoid structures.

SUBMITTER: McLauchlan IA 

PROVIDER: S-EPMC12593086 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature