Synthesis of naphth[2,1-a]azulenes via [8 + 2] cycloaddition of 2Hcyclohepta[b]furan-2-ones, and their reactivity, optical, and structural properties

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This is a Experimental Study study.

Taku Shoji; Akari Yamazaki; Miku Yoshida; Masafumi Yasunami; Takumi Kamayachi; Ikuo Uchiyama; Shigeki Mori; Tetsuo Okujima; Ryuta Sekiguchi; Shunji Ito

doi:10.1039/d5ob01492a

January 1, 2025Organic & Biomolecular Chemistry

Synthesis of naphth[2,1-a]azulenes via [8 + 2] cycloaddition of 2Hcyclohepta[b]furan-2-ones, and their reactivity, optical, and structural properties

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Key Points

The synthesis yielded a range of naphth[2,1-a]azulenes, showcasing their unique optical properties.
Reactivity studies reveal interactions with various enamines and silyl enol ethers derived from α-tetralones.
The approach uses [8 + 2] cycloaddition, contributing novel compounds to the field of synthetic organic chemistry.
Structural analysis supports the potential applications of these naphth[2,1-a]azulenes in material sciences.

Implication

[8 + 2] cycloaddition creates naphth[2,1-a]azulenes from 2Hcyclohepta[b]furan-2-ones, indicating diverse reactivity.

Abstract

A concise and efficient synthetic route to naphth[2,1-a]azulenes was developed via [8 + 2] cycloaddition of 2Hcyclohepta[b]furan-2-ones with enamines or a silyl enol ether derived from α-tetralones. A diverse array...

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Cite This Study

Shoji et al. (2025) studied this question.

synapsesocial.com/papers/68efd921056559ef428775ed https://doi.org/10.1039/d5ob01492a

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Synthesis of naphth[2,1-a]azulenes via [8 + 2] cycloaddition of 2Hcyclohepta[b]furan-2-ones, and their reactivity, optical, and structural properties

Key Points

Implication

Abstract

Discussion

Cite This Study

Synthesis of naphth[2,1-a]azulenes via [8 + 2] cycloaddition of 2Hcyclohepta[b]furan-2-ones, and their reactivity, optical, and structural properties

Key Points

Implication

Abstract

Discussion

Cite This Study

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