ArticleACS omega2024
Extending the Carbon Chain Length of Carbohydrate-Derived 5-Substituted-2-furaldehydes by Condensing with Active Methylene Compounds under Organocatalytic Conditions.
Article in ACS omega, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
This work reports a high-yielding, organic solvent-free, gram-scale synthesis of novel Knoevenagel condensation products by reacting carbohydrate-derived 5-substituted-2-furaldehydes (SFLs) with active methylene compounds (AMCs) using various organic amines and inorganic bases as catalysts. Among the base catalysts examined, piperidine performed best, affording satisfactory selectivity and yield of the targeted Knoevenagel condensation products owing to the subtle balance between its nucleophilicity and basicity. The reaction was optimized on various reaction parameters, such as temperature, duration, solvent, catalyst loading, and molar ratio of the reactants. Even though the SFLs exhibited significantly different reactivity, a general synthetic protocol was developed successfully, affording good to excellent isolated yields (70-96%) of the novel Knoevenagel condensation products at ambient temperature. Moreover, the Knoevenagel products were purified by triturating with eco-friendly solvents (e.g., ethyl acetate and
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