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Imidazo[1,2-a]pyridine derivatives synthesis from lignin β-O-4 segments via a one-pot multicomponent reaction.

ABSTRACT: The catalytic conversion of lignin into N-containing chemicals is of great significance for the realization of value-added biorefinery concept. In this article, a one-pot strategy was designed for the transformation of lignin β-O-4 model compounds to imidazo[1,2-a]pyridines in yields up to 95% using 2-aminopyridine as a nitrogen source. This transformation involves highly coupled cleavage of C-O bonds, sp³C-H bond oxidative activation, and intramolecular dehydrative coupling reaction to construction of N-heterobicyclic ring. With this protocol, a wide range of functionalized imidazo[1,2-a]pyridines sharing the same structure skeleton as those commercial drug molecules, such as Zolimidine, Alpidem, Saripidem, etc., were synthesized from different lignin β-O-4 model compounds and one β-O-4 polymer, emphasizing the application feasibility of lignin derivatives in N-heterobicyclic pharmaceutical synthesis.

SUBMITTER: Guo L

PROVIDER: S-EPMC10209544 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Imidazo[1,2-a]pyridine derivatives synthesis from lignin β-O-4 segments via a one-pot multicomponent reaction.

Guo Luxian L Ding Yangming Y Wang Hua H Liu Yuxuan Y Qiang Qian Q Luo Qi Q Song Fei F Li Changzhi C

iScience 20230509 6

The catalytic conversion of lignin into N-containing chemicals is of great significance for the realization of value-added biorefinery concept. In this article, a one-pot strategy was designed for the transformation of lignin β-O-4 model compounds to imidazo[1,2-a]pyridines in yields up to 95% using 2-aminopyridine as a nitrogen source. This transformation involves highly coupled cleavage of C-O bonds, sp<sup>3</sup>C-H bond oxidative activation, and intramolecular dehydrative coupling reaction ...[more]

PMID: 37250767

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