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An Easy Access to Furan-Fused Polyheterocyclic Systems.

Alice BenziLara BianchiGianluca GiorgiMassimo MaccagnoGiovanni PetrilloDomenico SpinelliCinzia Tavani
Published in: Molecules (Basel, Switzerland) (2022)
Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[ b ]thiophene with amines. Such versatile building blocks couple the well-recognized double electrophilic reactivity of the nitrovinyl moiety (addition to the double bond, followed by, e.g., intramolecular replacement of the nitro group) with the possibility to exploit a conjugated system of double bonds within an electrocyclization process. Herein, nitrostilbenes are reacted with different aromatic enols provided by a double (carbon and oxygen) nucleophilicity, leading to novel, interesting naphthodihydrofurans. From these, as a viable application, aromatization and electrocyclization lead in turn to valuable polycondensed, fully aromatic O -heterocycles.
Keyphrases
  • amino acid
  • molecular docking