924-44-7Relevant articles and documents
Friedel-Crafts reactions in water of carbonyl compounds with heteroaromatic compounds
Zhuang, Wei,Jorgensen, Karl Anker
, p. 1336 - 1337 (2002)
The development of Friedel-Crafts reaction in H2O of carbonyl compounds is presented; a series of different heteroaromatic compounds react with ethyl glyoxylate to give the Friedel-Crafts addition adducts in good yields in various H2O solutions.
Indolizines Enabling Rapid Uncaging of Alcohols and Carboxylic Acids by Red Light-Induced Photooxidation
Watanabe, Kenji,Terao, Nodoka,Kii, Isao,Nakagawa, Reiko,Niwa, Takashi,Hosoya, Takamitsu
supporting information, p. 5434 - 5438 (2020/07/24)
The irradiation of red light-emitting-diode light (λ = 660 nm) to 3-acyl-2-methoxyindolizines in the presence of a catalytic amount of methylene blue triggered the photooxidation of the indolizine ring, resulting in a nearly quantitative release of alcohols or carboxylic acids within a few minutes. The method was applicable for photouncaging various functional molecules such as a carboxylic anticancer drug and a phenolic fluorescent dye from the corresponding indolizine conjugates, including an insulin-indolizine-dye conjugate.
Asymmetric Catalytic Aza-Diels–Alder/Ring-Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis
Li, Yang,Barl?se, Casper,J?rgensen, Julie,Carlsen, Bj?rn Drei?,J?rgensen, Karl Anker
supporting information, p. 38 - 41 (2017/01/09)
An asymmetric catalytic aza-Diels–Alder/ring-closing cascade reaction between acylhydrazones and in situ formed trienamines is presented. The reaction proceeds through a formal aza-Diels–Alder cycloaddition, followed by a ring-closing reaction forming the hemiaminal ring leading to chiral bicyclic azaheterocycles in moderate to good yield (up to 71 %), good enantio- (up to 92 % ee) and diastereoselectivity (up to >20:1 d.r.). Furthermore, transformations are presented to show the potential application of the formed product.
A β-Carbon elimination strategy for convenient: In situ access to cyclopentadienyl metal complexes
Smits,Audic,Wodrich,Corminboeuf,Cramer
, p. 7174 - 7179 (2017/10/05)
The electronic and steric properties of tailored cyclopentadienyl (Cp) ligands are powerful handles to modulate the catalytic properties of their metal complexes. This requires the individual preparation, purification and storage of each ligand/metal combination. Alternative, ideally in situ, complexation protocols would be of high utility. We disclose a new approach to access Cp metal complexes. Common metal precursors rapidly react with cyclopentadienyl carbinols via β-carbon eliminations to directly give the Cp-metal complexes. An advantage of this is the direct and flexible use of storable pre-ligands. No auxiliary base is required and the Cp complexes can be prepared in situ in the reaction vessel for subsequent catalytic transformations.
Synthesis, structure and antiproliferative activity of chiral polyamines based on a 2-azanorbornane skeleton
Kamińska, Karolina,Wojaczyńska, El?bieta,Wietrzyk, Joanna,Turlej, Eliza,B?a?ejczyk, Agnieszka,Wieczorek, Robert
, p. 753 - 758 (2016/07/29)
A series of enantiopure 2-azanorbornane-based amines were prepared via a stereoselective aza-Diels–Alder reaction and further modifications of the obtained cycloadduct. In particular, derivatives containing two bicyclic moieties linked by [Formula presented] fragments were synthesized. Two dimeric derivatives exhibited a significant antiproliferative activity against selected cell lines, comparable to cisplatin in certain cases.
Importance of the Electron Correlation and Dispersion Corrections in Calculations Involving Enamines, Hemiaminals, and Aminals. Comparison of B3LYP, M06-2X, MP2, and CCSD Results with Experimental Data
Castro-Alvarez, Alejandro,Carneros, Héctor,Sánchez, Dani,Vilarrasa, Jaume
supporting information, p. 11977 - 11985 (2016/01/09)
While B3LYP, M06-2X, and MP2 calculations predict the δG° values for exchange equilibria between enamines and ketones with similar acceptable accuracy, the M06-2X/6-311+G(d,p) and MP2/6-311+G(d,p) methods are required for enamine formation reactions (for example, for enamine 5a, arising from 3-methylbutanal and pyrrolidine). Stronger disagreement was observed when calculated energies of hemiaminals (N,O-acetals) and aminals (N,N-acetals) were compared with experimental equilibrium constants, which are reported here for the first time. Although it is known that the B3LYP method does not provide a good description of the London dispersion forces, while M06-2X and MP2 may overestimate them, it is shown here how large the gaps are and that at least single-point calculations at the CCSD(T)/6-31+G(d) level should be used for these reaction intermediates; CCSD(T)/6-31+G(d) and CCSD(T)/6-311+G(d,p) calculations afford δG° values in some cases quite close to MP2/6-311+G(d,p) while in others closer to M06-2X/6-311+G(d,p). The effect of solvents is similarly predicted by the SMD, CPCM, and IEFPCM approaches (with energy differences below 1 kcal/mol).
Stereoselective preparation of chiral compounds in Mannich-type reactions of a bicyclic imine and phenols or indole Dedicated to Professor Jacek Skarzewski on the occasion of his 65th birthday
Iwanejko, Jakub,Wojaczyńska, Elzbieta,Wojaczyński, Jacek,B?kowicz, Julia
supporting information, p. 6619 - 6622 (2015/02/18)
Mannich-type reactions of a chiral bicyclic imine and various nucleophiles yield the corresponding adducts with good to high diastereoselectivity. The influence of the reaction conditions on the yield and stereochemical outcome is investigated. The configuration of the products is established by 1H NMR spectroscopy, and the major isomers of two adducts are characterized by X-ray crystallography.
METHOD FOR THE CATALYTIC REDUCTION OF ACID CHLORIDES AND IMIDOYL CHLORIDES
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Paragraph 0104, (2014/08/19)
The present application relates to methods for the catalytic reduction of acid chlorides and/or imidoyl chlorides. The methods comprise reacting the acid chloride or imidoyl chloride with a silane reducing agent in the presence of a catalyst such as [Cp(Pri3P)Ru(NCMe)2]+[PF6]?.
Linearization of carbohydrate derived polycyclic frameworks
Singh, Priyanka,Panda, Gautam
, p. 31892 - 31903 (2014/08/18)
We report easy access to carbohydrate derived diverse tricyclic skeletons which could be beneficial for exploring polyfunctionalized chiral alicycles. The key reaction to assemble a sugar fused tricyclic core is intermolecular tandem esterification and 1,3-dipolar cycloaddition. The framework was elaborated using amide forming reactions, opening of isoxazolidine rings followed by N and O-acylations. The sequences provide distinct, spatially separated and encoded chemical entities that may pave the way to investigate cell functions.
Monoimine derived from trans-1,2-diaminocyclohexane and ethyl glyoxylate: An intermediate in aza-Diels-Alder and Mannich reactions
Wojaczynska, Elzibieta,Baikowicz, Julia,Dorsz, Mateusz,Skarziewski, Jacek
, p. 2808 - 2811 (2013/04/23)
Novel enantiopure policyclic nitrogen heterocycles have been obtained in the diastereoselective aza-Diels-Alder or Mannich reaction of dienes with imine formed in situ from ethyl glyoxylate and (1R,2R)-diaminocyclohexane.
