26487-95-6Relevant academic research and scientific papers
A Direct Synthesis of Highly Substituted π-Rich Aromatic Heterocycles from Oxetanes
White, Alexander R.,Kozlowski, Ryan A.,Tsai, Shiou-Chuan,Vanderwal, Christopher D.
supporting information, p. 10525 - 10529 (2017/08/22)
The ubiquitous use of π-rich five-membered heterocycles has driven the development of new methods for their synthesis for more than a century. Here, we disclose a general and reliable reaction manifold for the construction of highly substituted heterocycles through a facile Lewis-acid-catalyzed oxetane rearrangement. Notably, this methodology employs a keto-oxetane motif as a 1,4-dicarbonyl surrogate, which can be synthesized using robust alkylation or alkenylation reactions, and thus obviates the need to access 1,4-dicarbonyl compounds via umpoled starting materials. We harnessed this reactivity to generate a broad range of substituted furans and pyrroles, and extended this methodology to produce benzo-fused versions thereof.
Preparation and chemistry of phosphoranyl-derived iodanes
Zhdankin, Viktor V.,Maydanovych, Olena,Herschbach, Jon,Bruno, Jessica,Matveeva, Elena D.,Zefirov, Nikolai S.
, p. 1018 - 1023 (2007/10/03)
The preparation and chemistry of novel phosphoranyl-derived λ3-iodanes is reported. The phosphoranyl-derived phenyliodonium sulfonates were prepared in good yields by the reaction of stabilized phosphonium ylides [1-triphenylphosphoranylidene-2-propanone, methyl(triphenylphosphoranylidene)acetate, (triphenylphosphoranylidene)acetaldehyde, and (triphenylphosphoranylidene)acetonitrile] with the pyridinium complex of iodobenzene ditriflate or with [hydroxy(tosyloxy)-iodo]benzene under mild conditions. These compounds represent a potentially useful class of reagents that combine in one molecule synthetic advantages of a phosphonium ylide and an iodonium salt. Specifically, phosphorane-derived phenyliodonium tosylates can react with soft nucleophiles, such as iodide, bromide, benzenesulfinate, and thiophenolate anions, with a selective formation of the respective α-functionalized phosphonium ylides, which can be further converted to alkenes by the Wittig reaction with benzaldehyde. The phosphoranyl-derived benziodoxoles can be prepared by the reaction of 1-acetoxybenziodoxole with stabilized phosphonium ylides. An unusual ligand exchange on the iodine(III) center resulting in the substitution of a carbon ligand with an oxygen ligand was observed in the reaction of these compounds with strong acids.
Syntheses of highly functionalised 6-substituted pteridines.
Guiney, Donie,Gibson, Colin L,Suckling, Colin J
, p. 664 - 675 (2007/10/03)
Methods for the synthesis of polyfunctional 6-substituted pteridines from the corresponding 6-aldehydes are described. Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy and dihydroxy functional groups have all been introduced principally through
Synthesis of C-glycosyl isoxazoles and branched-chain enuloses from 2,3-O-isopropylidene-D-glyceraldehyde
Bá?ez Sanz,López Sastre,Pati?o Molina,Romero-ávila García
, p. 1331 - 1350 (2007/10/03)
The synthesis of 5-glycosyl isoxazoles with 3-alkyl-, 3-aryl, 3,4-dialkyl, 3-aryl-4-alkyl or 3-alkyl-4-bromo substituents is reported. Deoxyenuloses were obtained from reaction of 2,3-O-isopropylidene-D-glyceraldehyde and several phosphorus ylides, which contain a carbonyl group, by a Wittig reaction. C-glycosyl α,β-unsaturated ketones were obtained, with the polyhydroxylate chain lengthened by two or three carbon atoms. In the second phase the ketones were transformed into the corresponding C-glycosyl α,β-unsaturated ketoximes, leading to the C-glycosyl isoxazoles, which were converted into the title compounds via removal of the isopropylidene group of suitably protected carbohydrates. The solubility of the synthetized C-glycosyl isoxazoles were modified by free hydroxyl groups in such a way that their behaviour against certain viruses and their potential antiviral activity could be studied.
