Journal of advanced research · 2025
Reactions of N-heterocyclic carbenes with nitrobenzenes: harnessing NHCs as synthetic building blocks.
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Zheng Zhiguo, Deng Youlin, Yang Xiaoqun, Jin Zhichao, Huang Shiqing, Wu Jian, Chi Yonggui Robin
Аннотация
INTRODUCTION: Quinazolin-4-one is a privileged scaffold in drugs with broad clinical applications. Conventionally, an o-amino group was generally needed to be pre-installed on the benzoic acid-derived starting materials for the efficient condensation reactions towards quinazolin-4-ones. The application of benzene derivatives without requisite amino and / or carbonyl groups as the quinazolin-4-one starting materials has not been disclosed. Therefore, we report herein the fabrication of NHC molecules with nitrobenzenes for facile access to quinazolin-4-one derivatives.
OBJECTIVES: To develop an unprecedented synthetic method utilizing nitrobenzenes and N-heterocyclic carbene (NHC) molecules, to elucidate the novel reaction mechanism through experimental and computational studies, to synthesize a series of quinazolin-4-one derivatives, and to evaluate their in vitro antibacterial activity.
METHODS: A synthetic method involving nitrobenzenes and NHC molecules was developed. The novel reaction mechanism was elucidated through isotopic labeling experiments and computational studies, and a series of quinazolin-4-one derivatives were synthesized. The synthesized compounds were evaluated for in vitro antifungal activity against four plant pathogens using the mycelial growth rate method.
RESULTS: We report for the first time an unprecedented synthetic method involving nitrobenzene and NHC molecules. The nitrobenzene substrate acts as a novel type of NHC acceptor, enabling a condensation reaction with the NHC molecule through a multi-step nucleophilic addition/rearrangement/dehydration cascade process. This conceptually novel reaction mechanism has been thoroughly investigated through experimental and computational studies. A variety of substituents with different electronic properties are tolerated on both the nitrobenzene and NHC reactants. A series of quinazolin-4-one products can be readily accessed using the current synthetic strategy, and they exhibit promising antifungal activity in plant protection.
CONCLUSION: We have developed a conceptually novel incorporation reaction between nitrobenzenes and NHC molecules. Synthesized compound 13 exhibited broad-spectrum antifungal activity, providing a basis for its development potential as a new framework for pesticide design.
OBJECTIVES: To develop an unprecedented synthetic method utilizing nitrobenzenes and N-heterocyclic carbene (NHC) molecules, to elucidate the novel reaction mechanism through experimental and computational studies, to synthesize a series of quinazolin-4-one derivatives, and to evaluate their in vitro antibacterial activity.
METHODS: A synthetic method involving nitrobenzenes and NHC molecules was developed. The novel reaction mechanism was elucidated through isotopic labeling experiments and computational studies, and a series of quinazolin-4-one derivatives were synthesized. The synthesized compounds were evaluated for in vitro antifungal activity against four plant pathogens using the mycelial growth rate method.
RESULTS: We report for the first time an unprecedented synthetic method involving nitrobenzene and NHC molecules. The nitrobenzene substrate acts as a novel type of NHC acceptor, enabling a condensation reaction with the NHC molecule through a multi-step nucleophilic addition/rearrangement/dehydration cascade process. This conceptually novel reaction mechanism has been thoroughly investigated through experimental and computational studies. A variety of substituents with different electronic properties are tolerated on both the nitrobenzene and NHC reactants. A series of quinazolin-4-one products can be readily accessed using the current synthetic strategy, and they exhibit promising antifungal activity in plant protection.
CONCLUSION: We have developed a conceptually novel incorporation reaction between nitrobenzenes and NHC molecules. Synthesized compound 13 exhibited broad-spectrum antifungal activity, providing a basis for its development potential as a new framework for pesticide design.