Journal
MOLECULES
Volume 27, Issue 10, Pages -Publisher
MDPI
DOI: 10.3390/molecules27103147
Keywords
nitrostilbenes; naphthofurans; cyclization; electrocyclization
Funding
- Genoa University [FRA 2019]
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Nitrostilbenes with different aryl substituents can be obtained from the initial ring-opening of 3-nitrobenzo[b]thiophene with amines. These versatile compounds exhibit diverse reactivity and can undergo electrocyclization to form novel naphthodihydrofurans. Aromatization and electrocyclization of these compounds further lead to valuable polycondensed O-heterocycles.
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.
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