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dc.contributor.authorLambu, Mallikharjuna Raoen_US
dc.contributor.authorJudeh, Zaher M. A.en_US
dc.identifier.citationLambu, 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.
dc.description.abstractCondensation 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.en_US
dc.description.sponsorshipNanyang Technological Universityen_US
dc.relationRG 142/16en_US
dc.relation.ispartofGreen Chemistryen_US
dc.rights© 2019 The Royal Society of Chemistry. All rights reserved.en_US
dc.subjectEngineering::Chemical engineeringen_US
dc.titleEfficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous mediaen_US
dc.typeJournal Articleen
dc.contributor.schoolSchool of Chemical and Biomedical Engineeringen_US
dc.subject.keywordsFunctionalized Furansen_US
dc.subject.keywordsUnprotected Carbohydratesen_US
dc.description.acknowledgementWe thank Nanyang Technological University, Singapore for financial help (RG 142/16).en_US
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