A more sustainable and greener process for preparing 3,4,5-trisubstituted furan-2-one derivatives
Document Type
Article
Publication Date
10-1-2023
Abstract
Treatment of 4,4 `-trimethylenedipiperidine with two equivalents of glacial acetic acid gave a cream-like liquid with a pale yellow color. Then, its ionic chemical structure was demonstrated by different spectroscopic techniques. The thermal behavior of the new ionic liquid was also studied by TGA/DTA and DSC techniques to record its phase transitions and thermal stability and compare those with another analog, i. e., 1H,4H-piperazine-N,N `-diium diacetate. Then, the multicomponent condensation of halogen-substituted benzaldehydes with dimethyl 2-(phenylamino) fumarate was investigated using the new ionic liquid in ethanol, an eco-friendly medium. Excellent yield with 100 % conversion was obtained and pure products could be isolated directly from ethanol. After separating pure products, the residue solution was employed in the next run without separation, concentration, purification, or activation. Furthermore, the synthesis of methyl 2-(4-chlorophenyl)-5-oxo-4-(phenylamino)-2,5-dihydro-furan-3-carboxylate was carried out on a large scale using the current catalytic process, affording a conversion of 100 % and a high yield of the crystalline product even after ten consecutive runs. Energy efficiency, cost- and time-saving, and waste prevention demonstrate the newly developed metal- and halogen-free catalysis as a more sustainable catalytic process for preparing 3,4,5-trisubstituted furan-2-one derivatives on the laboratory and industrial scale. A new halogen-free ionic liquid was synthesized and characterized by different spectroscopic analyses. Then, the thermal behavior of the new ionic liquid compared to its analog. In addition, the catalytic activity of new ionic liquid was demonstrated for greener preparation of various known and new 3,4,5-trisubstituted furan-2-one derivatives.image
Keywords
Ionic liquid, Sustainable chemistry, Organocatalysis, Multicomponent reaction, Waste prevention
Divisions
nanotechnology
Publication Title
ChemistrySelect
Volume
8
Issue
39
Publisher
Wiley
Publisher Location
POSTFACH 101161, 69451 WEINHEIM, GERMANY