Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/150625
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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