31053-73-3Relevant academic research and scientific papers
Simple Aza -conjugate addition methodology for the synthesis of isoindole nitrones and 3,4-dihydroisoquinoline nitrones
Peacock, Lucy R.,Chapman, Robert S. L.,Sedgwick, Adam C.,Bull, Steven D.,Mahon, Mary F.,Amans, Dominique
supporting information, p. 994 - 997 (2015/03/18)
Aryl-aldehydes containing ortho-substituted α,β-unsaturated carboxylic acid derivatives react with hydroxylamine to afford reactive N-hydroxy-carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford isoindole nitrones and 3,4-dihydroisoquinoline nitrones in good yield. Conditions have been developed to reduce these isoindole nitrones to their corresponding hydroxylamine, enamine, and amine derivatives. Isoindole nitrones react with dimethyl acetylenedicarboxylate (DMAD) via a [4 + 2]-cycloaddition/deamination pathway to afford substituted naphthalene derivatives, while 3,4-dihydroisoquinoline nitrones react with DMAD via a [1,3]-dipolar cycloaddition pathway to afford tricyclic heteroarenes.
Mesoporous poly-melamine-formaldehyde (mPMF)-a highly efficient catalyst for chemoselective acetalization of aldehydes
Tan, Mei Xuan,Gu, Liuqun,Li, Nannan,Ying, Jackie Y.,Zhang, Yugen
, p. 1127 - 1132 (2013/06/05)
A mesoporous poly-melamine-formaldehyde polymer with a high surface area, good porosity and a high density of amine and triazine functional groups was investigated as a highly efficient hydrogen-bonding catalyst. This porous organic polymer was found to be highly effective in catalyzing chemoselective acetalization of aldehydes, without the consumption of any dehydrating agents. The turnover frequency of mesoporous poly-melamine-formaldehyde is hundreds of times higher than melamine monomer, and this high efficiency is due to the high density of aminal (-NH-CH2-NH-) groups and triazine rings in the polymer network, which provides an inherently powerful system with multiple hydrogen bonds. This unique characteristic imparts mesoporous poly-melamine-formaldehyde polymer with a very high activity as a heterogeneous organocatalyst. The polymer is also low cost, and easy to be synthesized and recycled.
A METHOD OF ACETALIZING AN ALDEHYDE
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Page/Page column 22; 23; 24, (2013/09/26)
A method of acetalizing an aldehyde comprising reacting said aldehyde with an alcohol in the presence of a polymeric catalyst to form an acetal wherein the polymeric catalyst is a mesoporous poly-melamine-formaldehyde polymer.
An efficient photoinduced deprotection of aromatic acetals and ketals
Thevenet, Damien,Neier, Reinhard
experimental part, p. 331 - 346 (2011/04/22)
A novel type of photodeprotection reaction of simple aromatic acetals and ketals is described. The deprotection is highly efficient under optimized conditions. The aromatic ring confers the photoreactivity to the compounds. The efficiency of the process depends on the structure of the acetal moiety. The common minor side reaction, the photooxidation, becomes the major reaction pathway in the cases of cyclic acetals. The use of photon as only reagent makes this procedure especially attractive for acetal deprotection.
