Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media
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...
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sg-ntu-dr.10356-1506252021-08-04T02:03:20Z Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media Lambu, Mallikharjuna Rao Judeh, Zaher M. A. School of Chemical and Biomedical Engineering Engineering::Chemical engineering Functionalized Furans Unprotected Carbohydrates 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. Nanyang Technological University We thank Nanyang Technological University, Singapore for financial help (RG 142/16). 2021-08-04T02:03:20Z 2021-08-04T02:03:20Z 2019 Journal Article 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 1463-9262 https://hdl.handle.net/10356/150625 10.1039/C8GC03509A 4 21 821 829 en RG 142/16 Green Chemistry © 2019 The Royal Society of Chemistry. All rights reserved. |
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Engineering::Chemical engineering Functionalized Furans Unprotected Carbohydrates Lambu, Mallikharjuna Rao Judeh, Zaher M. A. Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
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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. |
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School of Chemical and Biomedical Engineering |
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School of Chemical and Biomedical Engineering Lambu, Mallikharjuna Rao Judeh, Zaher M. A. |
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Article |
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Lambu, Mallikharjuna Rao Judeh, Zaher M. A. |
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Lambu, Mallikharjuna Rao |
title |
Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
title_short |
Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
title_full |
Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
title_fullStr |
Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
title_full_unstemmed |
Efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
title_sort |
efficient, one-step, cascade synthesis of densely functionalized furans from unprotected carbohydrates in basic aqueous media |
publishDate |
2021 |
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https://hdl.handle.net/10356/150625 |
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1707774585560104960 |