Work

Extending the Carbon Chain Length of Carbohydrate-Derived 5-Substituted-2-furaldehydes by Condensing with Active Methylene Compounds under Organocatalytic Conditions

Year: 2024

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide 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 n -heptane) without chromatographic purification.

Source: ACS Omega

DOI: 10.1021/acsomega.4c04261

Authors: Poornachandra Shamanna Prabhakar, Asiful H. Seikh, Mohammad Rezaul Karim, Saikat Dutta

Institutions: National Institute of Technology Karnataka, King Saud University

Language: English

Topic: Catalysis for Biomass Conversion

Subfield: Biomedical Engineering

Field: Engineering

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $1,935

Funders: Department of Science and Technology, Ministry of Science and Technology, India, King Saud University, National Institute of Technology Karnataka, Surathkal, Science and Engineering Research Board