1129-37-9Relevant academic research and scientific papers
Acetic Anhydride-Acetic Acid as a New Dehydrating Agent of Aldoximes for the Preparation of Nitriles: Preparation of 2-Cyanoglycals
Kinfe, Henok H.,Mabasa, Jackie,Mabasa, Tommy F.,Makhubela, Banothile C. E.,Simelane, Mthokozisi,Vatsha, Banele
, p. 991 - 996 (2020)
Glycals, 1,2-unsatrated carbohydrates, are versatile building blocks for the synthesis of various scaffolds. Despite their potential to serve as suitable precursors in diversity-oriented synthesis, 2-cyanoglycals are less explored in terms of their synthesis and derivatization. Herein, we report a combination of Ac 2 O and AcOH as new and efficient dehydrating agent of aldoximes for the synthesis of 2-cyanoglycals. In comparison to the conventional dehydrating system of Ac 2 O-base (such as NaOH, NaOAc and K 2 CO 3), the current protocol provides superior yields and faster reaction rates. The scope and limitations of the dehydrating system are investigated.
Efficient preparation of aldoximes from arylaldehydes, ethylenediamine and Oxone in water
Xia, Jing-Jing,Wang, Guan-Wu
, p. 231 - 236 (2007)
The one-pot reaction of aromatic aldehydes, ethylenediamine and Oxone (2KHSO5·KHSO4·K2SO4) in pure water was found to unexpectedly afford aldoximes in excellent yields.
Dioxido-vanadium(V) complex catalyzed oxidation of alcohols and tandem synthesis of oximes: a simple catalytic protocol for C–N bond formation
Kurbah, Sunshine Dominic
, p. 905 - 918 (2021)
We report the synthesis of a vanadium(V) complex characterized by FT-IR and 1H NMR spectroscopy. The structure of the complex was established by single crystal X-ray crystallography. We also carried out the catalytic oxidation of benzyl alcohol, hetero-aryl alcohols and propargylic alcohols. Tandem synthesis of oximes from alcohols were also carried out using our vanadium(V) complex. The newly synthesized complex acts as a catalyst for oxidation reactions and tandem synthesis of oxime from alcohols.
A rapid and convenient method for the synthesis of aldoximes under microwave irradiation using in situ generated ionic liquids
Hajipour,Rafiee,Ruoho
, p. 114 - 118 (2010)
We have developed a chemoselective, simple and efficient method for the preparation of aldoximes using microwave irradiation in the presence of tribenzylamine or 1,4-diazabicyclo[2.2.2]octane or 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane bromide as bases and useful precursors for in situ generation of ionic liquids.
Cycloaddition Reactions of Benzonorbornadiene and Homonorbornadiene: New Isoxazoline and Pyridazine Derivatives
Adilo?lu, Yadigar,?ahin, Ertan,Tutar, Ahmet,Menzek, Abdullah
, p. 1917 - 1925 (2018)
Ten new isoxazoline derivatives were synthesized from the reactions of benzonorbornadiene and homonorbornadiene derivatives with nitrile oxides formed from benzaldehyde and 4-substituted benzaldehyde. Two new pyridazine derivatives were also synthesized from the reaction of the homonorbornadiene derivatives with 3,6-di (2-pyridyl)-s-tetrazine. It was seen that all cycloaddition reactions were realized as exo selectivity. Finally, γ-Gauche effect in the isoxazoline derivatives was discussed.
P2O5/SiO2 as an efficient reagent for the preparation of Z-aldoximes under solvent-free conditions
Eshghi, Hossein,Gordi, Zinat
, p. 1553 - 1557 (2005)
A facile and efficient method for the preparation of Z-aldoximes is improved by means of P2O5/SiO2 reagent in solvent-free media. Advantages of this method are the use of inexpensive and selective reagent, with high yields in simple operation, and short reaction time under solvent-free conditions. Copyright Taylor & Francis Inc.
A rapid and convenient synthesis of oximes in dry media under microwave irradiation
Hajipour, Abdol Reza,Mallakpour, Shadpour E.,Imanzadeh, Gholamhasan
, p. 228 - 229 (1999)
In a novel method, the reaction of hydroxylamine hydrochloride with a number of aldehydes and ketones under microwave irradiation and solventless 'dry' condition gave oximes in excellent yield.
Highly efficient retro-cycloaddition reaction of isoxazolino[4,5:1,2][60]- and -[70]fullerenes
Martin, Nazario,Altable, Margarita,Filippone, Salvatore,Martin-Domenech, Angel,Martinez-Alvarez, Roberto,Suarez, Margarita,Plonska-Brzezinska, Marta E.,Lukoyanova, Olena,Echegoyen, Luis
, p. 3840 - 3846 (2007)
(Chemical Equation Presented) Isoxazolino[4,5:1,2][60]- and -[70]fullerenes undergo an efficient retro-cycloaddition reaction to pristine fullerene by thermal treatment in the presence of an excess of a dienophile and Cu(II) catalysis, which can be selectively used in the presence of malonate or pyrrolidine cycloadducts. Trapping experiments using N-phenylmaleimide as dipolarophile have shown that the reaction mechanism occurs by thermal removal of the nitrile oxide 1,3-dipole, in a process which is favored by the presence of Cu(II) as the catalyst. The ESI-MS study supports the observed retrocycloaddition process for both C60 and C70 derivatives. In contrast to previous electrochemical retrocycloaddition processes observed in fulleropy-rrolidines, isoxazolinofullerenes were stable under oxidative conditions.
Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates
Himo, Fahmi,Lovell, Timothy,Hilgraf, Robert,Rostovtsev, Vsevolod V.,Noodleman, Louis,Sharpless, K. Barry,Fokin, Valery V.
, p. 210 - 216 (2005)
Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.
Different substituent effects on the supramolecular arrays in some (E)-halo- and nitro-benzaldehyde oximes: Confirmation of attractive π(C=N)···π(phenyl) interactions
Gomes, Ligia R.,Low, John N.,Van Mourik, Tanja,Früchtl, Herbert,De Souza, Marcus V.N.,Da Costa, Cristiane F.,Wardell, James L.
, p. 319 - 334 (2019)
The crystal structures and Hirshfeld surface analyses are reported for four aldoximes, (E)-X-C6 H4 CH=N-OH [X = 3-Cl (1), 4-F (2), 2-O2 N (3) and 4-O2 N (4)]. The strong classical O-H · · · N hydrogen bonds involving the oxime group generate C(3) chains in compound 1, in contrast to the R22 (6) dimers formed in compounds 2-4; such arrangements have been shown to be the most frequently found for oximes other than salicylaldoximes (2-hydroxybenzaldehyde oximes). In general, weaker intermolecular interactions involving the X substituents, as well as C-H · · · O and π · · · π interactions have significant effects on the supramolecular arrays generated in the aggegation. A further important interaction in compound 1, and to a lesser extent in compound 4, is a π(C=N) · · · π(phenyl) molecular stacking. A data base search has indicated that short Cg(C=N) · · · Cg(phenyl) distances, -1.
