Please use this identifier to cite or link to this item: http://localhost:8080/xmlui/handle/123456789/4041
Title: Base-Mediated Annulation of Electrophilic Benzothiophene with Naphthols and Phenols: Accessing Benzothiophene-Fused Heteroacenes
Authors: Akhil Krishnan, R
Sheba Ann, Babu
Nitha, P R
Sreeja, Thulasi
Jubi, John
Issue Date: 6-Jun-2022
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry; 87(12):8017-8027.
Abstract: A base-mediated annulation of 2-nitrobenzothiophenes with naphthols was realized for the synthesis of hitherto unknown class of heteroacenes, namely benzothieno[2,3-b]naphthofurans. By using naphthols with a hydroxyl group positioned at 1st or 2nd position, we could synthesize two positional isomers, benzothieno[2,3-b]naphtho[2,1-d]furans or benzothieno[2,3-b]naphtho[2,3-d]furans. The annulation was found to be general with a range of substituted 2-nitrobenzothiophenes and naphthols. This heteroannulation of benzothiophene was extended using a range of phenols affording the corresponding benzothieno[2,3-b]benzofurans in moderate yields. The basic photophysical properties of these heteroacenes were evaluated, and we also demonstrated the applicability of this annulation on the gram scale.
URI: https://pubs.acs.org/doi/full/10.1021/acs.joc.2c00645
Appears in Collections:2022



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