- Solvent-dependent effect by carbon dioxide on the photoreactions of (9-anthryl)alkylamines
-
The effect of CO2 on a photoreaction was first studied systematically by using (9-anthryl)alkylamines (APA, AEA, and AMA) as the starting compound. From close scrutiny of the results, the CO2 effect was clearly observed and was well rationalized by the previously reported novel solvent dependence of the amine-CO2 reversible reactions. For instance, the yield of the dimer (h-t from APA or AEA, h-t+h-h from AMA) obtained in MeOH or DMSO was higher under CO2 than under argon and this was ascribed to formation of either ammonium bicarbonate/carbonate in MeOH or carbamic acid in DMSO, which will prevent the nitrogen lone pair from being involved in electron-transfer reactions. In fact, the electron-transfer side reactions producing 1-3 in DMSO were strongly inhibited under CO2. Also, due to formation of noncovalent linkage between the ammonium cation and the carbamate anion in 2-PrOH, the proportion of h-h relative to h-t produced from AMA in 2-PrOH was increased by carrying out the reaction under CO2.
- Horiguchi, Masahiro,Ito, Yoshikatsu
-
-
Read Online
- Δ2-isoxazoline derivatives as antimicrobials
-
The inhibitory effect of newly synthesized C- (anthranyl and biphenyl)-5-substituted-δ2-isoxazolines were characterized by IR, 1H NMR, 13C NMR and CHN analysis and evaluated for their antimicrobial activity against differe
- Priya,Basappa,Rangappa
-
-
Read Online
- A catalytic regioselective procedure for the synthesis of aryl oximes in the presence of palladium nanoparticles
-
The synthesis of aryl oximes from aryl aldehyde derivatives was carried out using hydroxylamine hydrochloride and aluminum oxy hydroxide-supported palladium (Pd/AlO(OH) nanoparticles. The procedure is revealed via the regioselective synthesis of oxime der
- Demir, Emine,Goksu, Haydar,Orhan, Ersin
-
-
- New Low-Dimensional Perovskites Based on Lead Bromide
-
Abstract: The reactions of lead bromide with 7,7,8,8-tetracyanoquinodimethane and anthracen-9-ylmethanamine hydrobromide in dimethylformamide (DMF) afford the known low-dimensional perovskite {PbBr2(DMF)}n (I) with an impurity of a new hybrid 1D perovskite {Ca(DMF)6[PbBr3]2}n (II), which is isolated in the individual form and characterized by X-ray diffraction analysis. In the crystal of compound II, lead bromide forms infinite chains of PbBr5 octahedra with one vacant vertex between which calcium cations coordinated by the DMF molecules are arranged. The calcium cations presumably have got into the reaction mixture from water used for the washing of the reaction vessel for crystallization after the previous attempt of the synthesis. An attempt of the purposeful preparation of this hybrid 1D perovskite from various calcium salts as sources of this metal ion gives one more new low-dimensional perovskite {Ca(DMF)6[PbBr2.3Cl0.7]2}n (III) in which halide anions (bromide and chloride anions from lead bromide and calcium chloride, respectively) build up the coordination sphere of the lead ion to an octahedral one inducing no noticeable changes in the crystal packing compared to that of compound II. The X-ray diffraction results are deposited with the Cambridge Crystallographic Data Centre (CIF files CCDC nos. 2045586 (I), 2047219 (II), and 2047220 (III)).
- Isakovskaya,Nikovskii,Nelyubina, Yu. V.
-
p. 365 - 375
(2021/07/16)
-
- Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction
-
A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.
- Pan, Hongmei,Lu, Tong,Wu, Xuedan,Gu, Chengwen,Tao, Naili,Zhang, Biao,Wang, Ao,Chen, Guangmei,Zhang, Kehua,Cheng, Jie,Jin, Jie
-
supporting information
p. 2360 - 2364
(2019/11/11)
-
- HCl-mediated cascade cyclocondensation of oxygenated arylacetic acids with arylaldehydes: one-pot synthesis of 1-arylisoquinolines
-
In this paper, a concise, open-vessel synthesis of 1-arylisoquinolines is describedviaHCl-mediated intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild and one-pot reaction conditions. A plausible mechanism is proposed and discussed herein. In the overall reaction process, only water was generated as the byproduct. Various environmentally friendly reaction conditions are investigated for convenient transformationviathe (4C + 1C + 1N) annulation. This protocol provides a highly effective ring closureviathe formations of one carbon-carbon (C-C) bond, two carbon-nitrogen (C-N) bonds and one carbon-oxygen (C-O) bond.
- Hsueh, Nai-Chen,Chen, Shin-Mei,Lin, Chun-Yi,Chang, Meng-Yang
-
p. 1047 - 1059
(2021/02/16)
-
- Exploring isoxazoles and pyrrolidinones decorated with the 4,6-dimethoxy-1,3,5-triazine unit as human farnesyltransferase inhibitors
-
Unprecedented triazinyl-isoxazoles were afforded via an effective cycloaddition reaction between nitrile oxides and the scarcely described 2-ethynyl-4,6-dimethoxy-1,3,5-triazine as dipolarophile. The biological evaluation of the newly synthesized compounds showed that the inhibition of human farnesyltransferase by zinc complexation could be improved with triazine-isoxazole moieties. The replacement of the isoxazole unit by a pyrrolidin-2-one was detrimental to the inhibitory activity while the pyrrolidin-2-thione derivatives conserved the biological potential. The potential of selected compounds to disrupt protein farnesylation in Chinese hamster ovary (CHO) cells transfected with pEGFP-CAAX was also evaluated.
- Lucescu, Liliana,Ghinet, Alina,Shova, Sergiu,Magnez, Romain,Thuru, Xavier,Farce, Amaury,Rigo, Beno?t,Belei, Dalila,Dubois, Jo?lle,B?cu, Elena
-
-
- Synthesis and reactivity of platinum(II) triphenylphosphino complexes with aromatic aldoximes
-
trans-[Pt(μ-Cl)Cl(PPh3)]2 reacted with arylaldoximes in 1,2-dichloroethane to afford [PtCl2(PPh3){N(OH)[dbnd]CHAr}] (Ar = 3,4-dimethoxyphenyl, 1-naphthyl, 9-anthryl) where aldoxime ligands are N-coordinated to p
- Belli Dell' Amico, Daniela,Colalillo, Marialuigia,Labella, Luca,Marchetti, Fabio,Samaritani, Simona
-
supporting information
p. 181 - 186
(2017/09/30)
-
- Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes
-
A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
-
supporting information
p. 7397 - 7401
(2015/07/15)
-
- Copper(II)-promoted direct conversion of methylarenes into aromatic oximes
-
A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
- Yu, Jiatao,Lu, Ming
-
supporting information
p. 7397 - 7401
(2015/11/27)
-
- Highly selective oximation of aldehydes by reusable heterogeneous sandwich-type polyoxometalate catalyst
-
The selectivity of oximation of a variety of aliphatic aldehydes and polycyclic aromatic aldehydes as substrates has been greatly improved by applying a reusable heterogeneous sandwich-type polyoxometalate as catalyst under mild conditions.
- Zhao, Shen,Liu, Lu,Song, Yu-Fei
-
supporting information; experimental part
p. 9855 - 9858
(2012/10/08)
-
- Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
-
The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
- Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
-
p. 6482 - 6490
(2012/10/30)
-
- Biologically active hydroxymoyl chlorides as antifungal agents
-
Several oximes and oxime ethers have been developed as antimicrobial agents. A series of chlorooximes (hydroximoyl chlorides) have been synthesized and tested for antifungal activity under in-vitro conditions against Candida albicans, Candida parapsilosis, Candida glabrata, Candida krusei, Aspergillus fumigatus, Aspergilhis flaviis and Aspergillus niger. The derived antifungal activity has been compared with the corresponding oximes. The results show that most of the chlorooximes exhibit potent antifungal activity with anti-isomers showing better activity. It is observed that most of the chlorooximes show interesting antifungal activity (MICs ≤ 32 μg/mL) compared to oximes. Compound 3q (2,3-dimethoxy phenyl hydroxymoyl chloride) is the most active compound. This compound is active against all the Candida species (MIC 0.5 μg/mL) as well as filamentous fungi with MIC range of 2-4 μg/mL. This series of compounds are fungicidal in nature as evident from the MFC results.
- Ismail, Tabasum,Shafi, Syed,Singh, Parvinder Pal,Qazi, Naveed Ahmed,Sawant, Sanghapal D.,Ali, Intzar,Khan, Inshad Ali,Kumar,Qazi, Ghulam Nabi,Alam, M. Sarwar
-
p. 740 - 747
(2008/12/20)
-
- Reduction of aldehydes and oximes to their corresponding alcohols and amines by catalytic hydrogenation method
-
The reduction of aldehydes such as 2-butyl-5-chloro-3H-imidazole-5- carbaldehyde and veratraldehyde, which are pharmaceutical key intermediates, have been reduced to alcohols by catalytic hydrogenation method in the presence of magnesium and also oximes are reduced to primary amines successively by magnesium/ammonium formate system, is a large scale feasible and cheaper method. The crystal structure of the product, (2-butyl-5-chloro-3H-imidazole-4-yl)- methanol 1 is reported.
- Basappa,Doreswamy,Mahendra,Mantelingu,Sridhar,Prasad, J. Shashidhara,Rangappa
-
p. 148 - 151
(2007/10/03)
-
- Homolytic Bond Dissociation Energies of the Acidic C-H Bonds in α-Substituted and 10-Substituted 9-Methylanthracenes and Their Related Radical Anions
-
Equilibrium acidities (pKHA), reduction potentials Ere(HA), oxidation potentials EOX(HA), and oxidation potentials of the conjugate anions EOX(A-) have been measured in dimethyl sulfoxide (DMSO) solution for 13 α-substituted 9-methylanthracenes (9-GCH2An) and 11 10-substituted 9-methylanthracenes (10-G-9-MeAn).The equilibrium acidities have been shown to be linearly correlated with Hammett ?- constants.The similar ρ- values for the linear correlations of pKHA vs ?- for 9-GCH2An (ρ- = 13.8) and 10-G-9-MeAn (ρ- = 14.2) demonstrate that the like substituents in 9-GCH2An and 10-G-9-MeAn have similar large effects on the equilibrium acidities.Suitable combinations of these equilibrium acidities with the reduction and oxidation potentials led to estimates of (a) the homolytic bond dissociation energies (BDEHA) of the acidic C-H bonds in 9-GCH2An and 10-G-9-MeAn, (b) the homolytic bond dissociation energies (BDEHA*-%) of the acidic C-H bonds in 9-GCH2An*- and 10-G-9-MeAn*- radical anions, and (c) the radical cation acidities (pKHA*+%) of the 9-GCH2An*+ and 10-G-9-MeAn*+ radical cations.Introduction of α-CN and α-NO2 groups had opposite effects on the strengths (BDEHA) of the acidic C-H bonds in 9-GCH2An; the α-CN group decreased the BDEHA value by 2.5 kcal/mol and the α-NO2 increased the BDEHA value by 4.5 kcal/mol, but they both weakened the acidic C-H bonds in 9-GCH2An*- radical anions (by 10.6 and 12.5 kcal/mol, respectively).The BDEs of the acidic C-H bonds in 10-G-9-MeAn were estimated to be 81.3 +/- 1.3 kcal/mol and those in the corresponding radical anions were estimated to be 58.5 +/- 2.5 kcal/mol.The 9-GCH2An*+ and 10-G-9-MeAn*+ radical cations are strongly acidic with the pKHA*+% values estimated in the range of -5 to -11 pKHA*+% units.Seven linear free energy relationships have been observed.
- Zhang, Xian-Man,Bordwell, Frederick G.,Bares, Joseph E.,Cheng, Jin-Pei,Petrie, Brian C.
-
p. 3051 - 3059
(2007/10/02)
-