Energy-Barrier-less Synthesis of Hexaaza-trifuranacyclopentadecaphane-hexaene at Ambient Temperature.

A thermochemically stable furan-based hexaaza-trifuranacyclopentadecaphane-hexaene (AF-cpdp) as a π 12 12 cyclic-conjugated color enriched heterocycle has been synthesized at ambient temperature. An energy-barrier-less (EBL) dehydrative azine formation of 2,5-diformylfuran (DFF) with hydrazine hydrate (N 2 H 4 ·H 2 O) followed by a single-arm heteroconjugation and ring formation at the final step under classical and mechanochemical approaches, avoiding external heating, was conducted for construction of a novel and highly stable cyclopentadecaphene (cpdp) conjugated system. The developed protocol is simple, energy-efficient, atom-economical, and easy to scale-up.