2007
DOI: 10.1016/j.ejmech.2006.09.021
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Pharmacophoric 2-hydroxyalkyl benzenesulfonamide: A single-step synthesis from benzenesulfonamide via hemiaminal

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Cited by 8 publications
(2 citation statements)
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“… , Among these fluoroalkylated compounds, the fluoroalkyl β-aminoalcohols as a privileged structural motif are widely found in β-secretase inhibitors, which are potent drugs used in the Alzheimer’s disease . Despite the great synthetic utility of this structure, there remains a formidable challenge in accessing a broad range of fluoroalkyl β-aminoalcohols with an asymmetric catalytic method. , In this context, we synthesized a novel fluoroalkylated hemiaminal 1 from sulfamide derivatives and successfully employed it in a dehydrated Mannich reaction . This reaction provided a reliable and scalable access to a broad spectrum of biologically active fluoroalkyl β-amino alcohols by a facile derivatization (Figure ).…”
mentioning
confidence: 99%
“… , Among these fluoroalkylated compounds, the fluoroalkyl β-aminoalcohols as a privileged structural motif are widely found in β-secretase inhibitors, which are potent drugs used in the Alzheimer’s disease . Despite the great synthetic utility of this structure, there remains a formidable challenge in accessing a broad range of fluoroalkyl β-aminoalcohols with an asymmetric catalytic method. , In this context, we synthesized a novel fluoroalkylated hemiaminal 1 from sulfamide derivatives and successfully employed it in a dehydrated Mannich reaction . This reaction provided a reliable and scalable access to a broad spectrum of biologically active fluoroalkyl β-amino alcohols by a facile derivatization (Figure ).…”
mentioning
confidence: 99%
“…Furthermore, in order to demonstrate the versatility of our method, a series of cyclic six- and five-membered ring α-iminophosphonates were also synthesized by the combination of slightly modified literature procedures (Scheme ). Readily available salicylaldehyde and N - tert -butylbenzenesulfonamide were used as the starting materials and converted to the sulfonylimine intermediates 6 , followed by nucleophilic addition of phosphites to afford α-aminophosphonates 7 and oxidation dehydrogenation. Notably, for the selective dehydrogenation process of α-aminophosphonates 7 , only freshly prepared manganese dioxide gave high yield and selectivity.…”
mentioning
confidence: 99%