Liu, Yuxuan, Luo, Qi, Qiang, Qian, Wang, Hua, Ding, Yangming, Wang, Chao, Xiao, Jianliang 
ORCID: 0000-0003-2010-247X, Li, Changzhi and Zhang, Tao
(2022)
Successive Cleavage and Reconstruction of Lignin beta-O-4 Models and Polymer to Access Quinoxalines.
CHEMSUSCHEM, 15 (21).
e202201401.
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Successive cleavage and reconstruction of lignin models AAM.pdf - Author Accepted Manuscript Download (936kB) | Preview |
Abstract
The construction of N-heterocyclic compounds from lignin remains a great challenge due to the complex lignin structure and the involvement of multiple steps, including the cleavage of lignin C-O linkages and the formation of heterocyclic aromatic rings. Herein, the first example of KOH mediated sustainable synthesis of quinoxaline derivatives from lignin β-O-4 model compounds in a one-pot fashion under transition-metal-free conditions has been achieved. Mechanistic studies suggested that this transformation includes highly coupled cascade steps of cleavage of C-O bonds, dehydrative condensation, sp<sup>3</sup> C-H bond oxidative activation, and intramolecular dehydrative coupling reaction. With this protocol, a wide range of functionalized quinoxalines, including an important drug compound AG1295, were synthesized from lignin β-O-4 model compounds and β-O-4 polymer, showcasing the application potential of lignin in pharmaceutical synthesis.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | biomass, lignin, N-heterocyclic compounds, quinoxalines, transition-metal-free |
| Divisions: | Faculty of Science and Engineering > School of Physical Sciences |
| Depositing User: | Symplectic Admin |
| Date Deposited: | 19 Apr 2023 08:55 |
| Last Modified: | 02 Sep 2023 01:30 |
| DOI: | 10.1002/cssc.202201401 |
| Related URLs: | |
| URI: | https://livrepository.liverpool.ac.uk/id/eprint/3169724 |
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