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|Title:||Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media||Authors:||Lambu, Mallikharjuna Rao
Judeh, Zaher M. A.
|Keywords:||Engineering::Chemical engineering||Issue Date:||2019||Source:||Lambu, M. R. & Judeh, Z. M. A. (2019). Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media. Green Chemistry, 21(4), 821-829. https://dx.doi.org/10.1039/C8GC03509A||Project:||RG 142/16||Journal:||Green Chemistry||Abstract:||Condensation of unprotected carbohydrates with malononitrile or malonamide nitrile in basic aqueous media gave in one-pot densely functionalized polyhydroxyalkyl 2-amino-3-furanonitriles and polyhydroxyalkyl 2-amino-3-furanocarboxamides in excellent 84–98% yields. Disaccharides afforded novel furano-glycosides. Based on the rate of formation of the furans, the ability of the tested bases to catalyze the reaction was concluded as Et₃N > DBU > K₂CO₃ > NaOMe. The reaction mechanism involved the formation of bicyclic furan-furan and furan-pyran intermediates observed for the first time. The reaction proceeded through a cascade mechanism involving Knoevenagel condensation, Oxo-Micheal addition, Thorpe-Ziegler type reaction and ring-opening-induced aromatization. This operationally simple and metal-free reaction proceeded with exclusive chemo-, regio-, and stereo-selectivities under environmentally benign conditions. As demonstrated on a 2 g scale, it holds promise for application in the large-scale synthesis of important intermediates such as densely functionalized furfural.||URI:||https://hdl.handle.net/10356/150625||ISSN:||1463-9262||DOI:||10.1039/C8GC03509A||Rights:||© 2019 The Royal Society of Chemistry. All rights reserved.||Fulltext Permission:||none||Fulltext Availability:||No Fulltext|
|Appears in Collections:||SCBE Journal Articles|
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