Synthesis of Azulene Derivatives from 2 H-Cyclohepta[ b]furan-2-ones as Starting Materials: Their Reactivity and Properties

Taku Shoji; Shunji Ito; Masafumi Yasunami

doi:10.3390/ijms221910686

Synthesis of Azulene Derivatives from 2 H-Cyclohepta[ b]furan-2-ones as Starting Materials: Their Reactivity and Properties

Int J Mol Sci. 2021 Oct 1;22(19):10686. doi: 10.3390/ijms221910686.

Authors

Taku Shoji¹, Shunji Ito², Masafumi Yasunami³

Affiliations

¹ Department of Material Science, Graduate School of Science and Technology, Shinshu University, Matsumoto 390-8621, Japan.
² Graduate School of Science and Technology, Hirosaki University, Hirosaki 036-8561, Japan.
³ Department of Chemical Biology and Applied Chemistry, College of Engineering, Nihon University, Koriyama 963-8642, Japan.

Abstract

A variety of synthetic methods have been developed for azulene derivatives due to their potential applications in pharmaceuticals and organic materials. Particularly, 2H-cyclohepta[b]furan-2-one and its derivatives have been frequently used as promising precursors for the synthesis of azulenes. In this review, we describe the development of the synthesis of azulenes by the reaction of 2H-cyclohepta[b]furan-2-ones with olefins, active methylenes, enamines, and silyl enol ethers as well as their reactivity and properties.

Keywords: 2H-cyclohepta[b]furan-2-one; azulene; cycloaddition; enamine; silyl enol ether.

Publication types

Review

MeSH terms

Azulenes / chemical synthesis*
Azulenes / chemistry
Chemistry Techniques, Synthetic
Cycloaddition Reaction
Ethers
Furans / chemistry*
Molecular Structure
Spectrum Analysis
Stereoisomerism

Substances

Azulenes
Ethers
Furans