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Switchable synthesis of natural-product-like lawsones and indenopyrazoles through regioselective ring-expansion of indantrione

Chemistry

Switchable synthesis of natural-product-like lawsones and indenopyrazoles through regioselective ring-expansion of indantrione

B. Hu, W. Yan, et al.

Discover a groundbreaking method for synthesizing lawsones and indenopyrazoles through a metal-free, ring-expansion reaction using indantrione and diazomethanes. This innovative approach, conducted by Bingwei Hu, Wenxin Yan, Peiyun Jiang, Ling Jiang, Xu Yuan, Jun Lin, Yinchun Jiao, and Yi Jin, showcases excellent yields and diastereoselectivity, revealing significant potential for synthetic applications.

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Playback language: English
Abstract
Lawsones and indenopyrazoles are prevalent structural motifs in pharmaceuticals and bioactive molecules, but their synthesis remains challenging. This paper presents a metal-free, ring-expansion reaction of indantrione with diazomethanes (generated in situ) to synthesize lawsone and indenopyrazole derivatives. The reaction is solvent-controlled, producing lawsones in acetonitrile and indenopyrazoles in alcohol solvents, with good yields and high diastereoselectivity. DFT calculations explored the mechanism in different solvents, and synthetic applications demonstrate the method's potential.
Publisher
Communications Chemistry
Published On
Jan 18, 2023
Authors
Bingwei Hu, Wenxin Yan, Peiyun Jiang, Ling Jiang, Xu Yuan, Jun Lin, Yinchun Jiao, Yi Jin
Tags
lawsones
indenopyrazoles
metal-free synthesis
ring-expansion reaction
diazomethanes
solvent-controlled reaction
DFT calculations

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