The Rapid Synthesis of π-Extended Azacorannulenes

S. Ito*
J. Synth. Org. Chem. Jpn.(有機合成化学協会誌) 2019, 77, 1128–1135.  DOI: 10.5059/yukigoseikyokaishi.77.1128

Abstract: In this account we describe our recent development of rapid syntheses of π-extended azacorannulenes. The key to successful synthesis is the use of polycyclic aromatic azomethine ylides, which exhibit extremely high reactivity in sequential 1,3-dipolar cycloadditions with alkenes and alkynes followed by oxidation to form fused pyrroles. This efficient construction of the polycyclic pyrrole structure has led to the rapid synthesis of various π-extended azacorannulenes, which are characterized by their extended π-surface and highly curved, bowl-shaped structures. The present study provides useful insights toward the bottom-up synthesis and property elucidation of heteroatom-containing fullerenes and their fragment molecules.

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