Three kinds of fused porphyrinoids, L2-L4, possessing different types of corrole-based frameworks were synthesized from a pyrrole-substituted corrole isomer (norrole L1). Oxidation of L1 afforded a unique N-Cmeso-fused pyrrolyl isonorrole L2, involving the fusion of an auxiliary pyrrolic NH moiety with a meso-sp3-hybridized carbon atom. Subsequently, L2 underwent macrocycle transformations to give singly and doubly N-CAr-fused N-confused corroles, L3 and L4, respectively. L3 and L4 contain fused [184.108.40.206]-tetra- and [220.127.116.11.6.5]-hexacyclic structures, respectively, prepared through lateral annulation. These skeletal transformation reactions from norrole to its isomer isonorrole and finally to N-confused corrole indicate that multiply fused porphyrinoids could be readily synthesized from pyrrole-appended confused porphyrinoids.
All Science Journal Classification (ASJC) codes
- 化学 (全般)