4.6 Article

An Easy Access to Furan-Fused Polyheterocyclic Systems

Journal

MOLECULES
Volume 27, Issue 10, Pages -

Publisher

MDPI
DOI: 10.3390/molecules27103147

Keywords

nitrostilbenes; naphthofurans; cyclization; electrocyclization

Funding

  1. Genoa University [FRA 2019]

Ask authors/readers for more resources

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.

Authors

I am an author on this paper
Click your name to claim this paper and add it to your profile.

Reviews

Primary Rating

4.6
Not enough ratings

Secondary Ratings

Novelty
-
Significance
-
Scientific rigor
-
Rate this paper

Recommended

No Data Available
No Data Available