Issue 2, 2024

Unprecedented linear products by a mechanochemically activated Biginelli reaction using lawsone

Abstract

The Biginelli reaction, a crucial multicomponent reaction, was investigated involving 2-hydroxy-1,4-naphthoquinone (lawsone), p-substituted benzaldehydes, and ureas. Surprisingly, the classic Biginelli cyclized DHPM was not observed under various experimental conditions. Mechanochemical conditions, unlike traditional liquid phase conditions, led to the unprecedented formation of a series of ‘Biginelli-linear’ lawsone derivatives with high yields. The observed outcomes were consistent with DFT theoretical predictions, highlighting the preference for the Michael adduct under liquid conditions and the energetically implausible cyclization pathway for the classic DHPM compound. Additionally, the study achieved the novel cyclization of a ‘Biginelli-linear’ lawsone derivative into a cyclic carbamate for the first time.

Graphical abstract: Unprecedented linear products by a mechanochemically activated Biginelli reaction using lawsone

Supplementary files

Article information

Article type
Paper
Submitted
18 Dec 2023
Accepted
12 Mar 2024
First published
02 Apr 2024
This article is Open Access
Creative Commons BY-NC license

RSC Mechanochem., 2024,1, 167-175

Unprecedented linear products by a mechanochemically activated Biginelli reaction using lawsone

C. L. Koumpoura, L. Vendier, C. Bijani, A. Robert, P. Carbonnière, J. Sotiropoulos and M. Baltas, RSC Mechanochem., 2024, 1, 167 DOI: 10.1039/D3MR00032J

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