AI Article Synopsis
- A base-mediated method was developed to create a new class of compounds called benzothieno[2,3-]naphthofurans by combining 2-nitrobenzothiophenes with naphthols.
- By selecting naphthols with specific hydroxyl positions, researchers synthesized two isomeric forms of these compounds.
- The process was found effective for different substituted compounds and extended to phenols, producing benzothieno[2,3-]benzofurans, while evaluating their basic photophysical properties and demonstrating scalable production.
Article 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-]naphthofurans. By using naphthols with a hydroxyl group positioned at 1st or 2nd position, we could synthesize two positional isomers, benzothieno[2,3-]naphtho[2,1-]furans or benzothieno[2,3-]naphtho[2,3-]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-]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.
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