An Easy Access to Furan-Fused Polyheterocyclic Systems

Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[ ]thiophene with amines. Such versatile building blocks couple the well-recognized double electrophilic reactivity of the nitrovinyl moiety (addition t...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-05, Vol.27 (10), p.3147
Main Authors: Benzi, Alice, Bianchi, Lara, Giorgi, Gianluca, Maccagno, Massimo, Petrillo, Giovanni, Spinelli, Domenico, Tavani, Cinzia
Format: Article
Language:English
Subjects:
Alcohols
Amines
Carbon - chemistry
Chemical properties
Chromatography
cyclization
electrocyclization
Furans
Furans - chemistry
Heterocyclic compounds
Investigations
naphthofurans
nitrostilbenes
Optical properties
Ring opening
Thiophenes
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Description
Summary:Nitrostilbenes characterized by two different or differently substituted aryl moieties can be obtained from the initial ring-opening of 3-nitrobenzo[ ]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 -heterocycles.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27103147