24207-38-3Relevant academic research and scientific papers
OXAZOLINE COMPOUND, CROSSLINKER AND RESIN COMPOSITION
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Paragraph 0036, (2019/03/07)
PROBLEM TO BE SOLVED: To provide an oxazoline compound and trioxazoline compound optimal as crosslinkers for a wide range of uses, including a coating agent, ink, a film, a binder, and adhesive or the like. SOLUTION: The present invention provides an oxazoline compound represented by the following chemical formula, a trioxazoline compound obtained by trifunctionalizing the oxazoline compound represented by the following chemical formula, and a crosslinker and a resin composition using the oxazoline compound or the trioxazoline compound. In the formula, X is H or R-OH, R is a C1-4 linear or branched alkylene group. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPO&INPIT
Fast synthesis of amides from ethyl salicylate under microwave radiation in a solvent-free system
Lima, Rafaely N.,Silva, Valdenizia R.,De Santos, Luciano,Bezerra, Daniel P.,Soares, Milena B. P.,Porto, André L. M.
, p. 56566 - 56574 (2017/12/26)
In this study, amide bond formation, one of the most important reactions in organic chemistry, it was evaluated using ethyl salicylate and ten different primary amines. Under the optimized experimental conditions, i.e. 60 °C, hexane, phenylboronic acid-PBA (15 mol%), boric acid-BA (15 mol%) or without catalyst-WC, using a hot-plate for 24 h, amides were obtained in excellent isolated yields (WC, 77-94% to S-Aa-Ad; PBA, 11-94% to S-Ae-Aj; and BA, 28-90% to S-Ae-Aj). The reaction employing CAL-B also permitted a moderate conversion for the production of amides S-Ae-Aj (3-42%). However, in our efforts to reduce the amide synthesis time (24 h), the reactions were performed in the presence of microwave-MW radiation using a free-solvent system [60 °C, PBA (15 mol%) or WC], which reduced the time of the reaction by 32-fold (45 min) and afforded nine amides (S-Aa-Ah and S-Aj) in 80-99% isolated yield and S-Ai in 23% yield. A cytotoxicity assay demonstrated that the amide S-Ag was capable of inhibiting four human tumor cell lines (MCF-7, HCT116, HepG2, and HL-60) with an IC50 ranging from 8.68 to 17.57 μg mL-1. In this study, MW radiation provided an attractive way for faster reactions, improved yields, and cleaner reactions, as well as the synthesis of amide S-Ag with cytotoxic activity.
New sky-blue and bluish-green emitting Ir(III) complexes containing an azoline ancillary ligand for highly efficient PhOLEDs
Sarada, Ganguri,Sim, Bomi,Cho, Woosum,Yoon, Juho,Gal, Yeong-Soon,Kim, Jang-Joo,Jin, Sung-Ho
, p. 60 - 68 (2016/04/26)
Two Ir(III) complexes containing the chromophoric ancillary ligands 2-(4,5-dihydrooxazol-2-yl)phenol and 2-(1-ethyl-4,5-dihydro-1H-imidazol-2-yl)phenol, and a highly functionalized phenylpyridine derivative, 3-(4-(tert-butyl)pyridin-2-yl)-2,6-difluorobenzonitrile, as a cyclometalating ligand were designed and synthesized. The oxazoline/imidazoline heterocycle of the ancillary ligand has the effect of enhancing the metal to ligand charge transfer transition nature of the emitting excited state and the fluorine and cyano substituents on the ligand have enriched the intersystem crossings, as indicated by the experimental photoluminescence analysis. As a result, the oxazoline and imidazoline containing complexes exhibited high photoluminescence quantum yields of about >90% with bright sky-blue emission at 480 nm and bluish-green light at 495 nm, respectively, along with excellent thermal/morphological stability about 400 °C and good solubility, that make them suitable for both wet- and dry-processes. In particular, the phosphorescent OLEDs fabricated by a dry-process showed the maximum EQEs of 21.9% and 19.7% for the oxazoline and imidazoline containing complexes, respectively.
Synthesis of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole moiety: Their in vitro evaluation against PDE4B
Rao, Raja Mohan,Luther, Bethala Jawahar,Rani, Chekuri Sharmila,Suresh, Namburi,Kapavarapu, Ravikumar,Parsa, Kishore V.L.,Rao, Mandava V. Basaveswara,Pal, Manojit
, p. 1166 - 1171 (2014/03/21)
A number of 2H-1,3-benzoxazin-4(3H)-one derivatives containing indole or benzofuran moieties were synthesized by using Pd/C-Cu mediated coupling-cyclization strategy as a key step. The o-iodoanilides or o-iodophenol were coupled with 3-{2-(prop-2-ynyloxy)ethyl}-2H-benzo[e][1,3]oxazin-4(3H)-one using 10%Pd/C-CuI-PPh3 as a catalyst system and Et3N as a base to give the target compounds. All the synthesized compounds were tested for their PDE4B inhibitory potential in vitro using a cell based cAMP reporter assay. Some of them showed fold increase of the cAMP level when tested at 30 μM. A representative compound showed encouraging PDE4B inhibitory properties that were supported by its docking results.
Living cationic ring-opening polymerization of 2-oxazolines initiated by rare-earth metal triflates
Hu, Fangyu,Xie, Shoulei,Jiang, Liming,Shen, Zhiquan
, p. 59917 - 59926 (2015/02/19)
The cationic ring-opening polymerization (CROP) of substituted 2-oxazolines using rare-earth metal triflates (RE(OTf)3) as initiator was investigated for the first time. In this work, we examined the polymerization characteristics of 2-ethyl-2-oxazoline (EtOx) initiated by Sc(OTf)3 under conventional thermal heating and microwave irradiation, and compared the respective outcomes with those obtained with the most frequently used initiator methyl tosylate (MeOTs). The results indicated that Sc(OTf)3 exhibits a higher catalytic efficiency to the EtOx polymerization than MeOTs under identical conditions. The controlled/living nature of the Sc(OTf)3-catalyzed CROP was confirmed by its linear first-order kinetics and the narrow molecular weight distribution of the resultant polymers as well as the block copolymerization of EtOx and 2-phenyl-2-oxazoline (PhOx). Based on in situ NMR spectroscopic studies and SEC analysis of PEtOx samples obtained from the control termination experiments, a possible initiating/propagating mechanism has been proposed for the living cationic ring-opening polymerization. Morever, this rare-earth catalytic system can also be applied to the ring-opening polymerization of some sterically hindered or aryl-substituted 2-oxazolines.
Oxorhenium(V) complexes with phenolate-oxazoline ligands: Influence of the isomeric form on the O-atom-transfer reactivity
Schachner, J?rg A.,Terfassa, Belina,Peschel, Lydia M.,Zwettler, Niklas,Belaj, Ferdinand,Cias, Pawel,Gescheidt, Georg,M?sch-Zanetti, Nadia C.
, p. 12918 - 12928 (2015/02/19)
The bidentate phenolate-oxazoline ligands 2-(2′-hydroxyphenyl)-2-oxazoline (1a, Hoz) and 2-(4′,4′-dimethyl-3′,4′-dihydrooxazol-2′-yl)phenol (1b, Hdmoz) were used to synthesize two sets of oxorhenium(V) complexes, namely, [ReOCl2(L)(PPh3)] [L = oz (2a) and dmoz (2b)] and [ReOX(L)2] [X = Cl, L = oz (3a or 3a′); X = Cl, L = dmoz (3b); X = OMe, L = dmoz (4)]. Complex 3a′ is a coordination isomer (N,N-cis isomer) with respect to the orientation of the phenolate-oxazoline ligands of the previously published complex 3a (N,N-trans isomer). The reaction of 3a′ with silver triflate in acetonitrile led to the cationic compound [ReO(oz)2(NCCH3)](OTf) ([3a′](OTf)). Compound 4 is a rarely observed isomer with a trans-O=Re-OMe unit. Complexes 3a, 3a′, [3a′](OTf), and 4 were tested as catalysts in the reduction of a perchlorate salt with an organic sulfide as the O acceptor and found to be active, in contrast to 2a and 2b. A comparison of the two isomeric complexes 3a and 3a′ showed significant differences in activity: 87% 3a vs 16% 3a′ sulfoxide yield. When complex [3a′](OTf) was used, the yield was 57%. Density functional theory calculations circumstantiate all of the proposed intermediates with N,N-trans configurations to be lower in energy compared to the respective compounds with N,N-cis configurations. Also, no interconversions between N,N-trans and N,N-cis configurations are predicted, which is in accordance with experimental data. This is interesting because it contradicts previous mechanistic views. Kinetic analyses determined by UV-vis spectroscopy on the rate-determining oxidation steps of 3a, 3a′, and [3a′](OTf) proved the N,N-cis complexes 3a′ and [3a′](OTf) to be slower by a factor of ～4.
A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
Balkrishna, Shah Jaimin,Kumar, Sangit
, p. 1417 - 1426 (2012/06/30)
An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
Synthesis and biological evaluation of some new 2-oxazoline and salicylic acid derivatives
Djurendic, Evgenija,Vujaskovic, Sanja Dojcinovic,Sakac, Marija,Ajdukovic, Jovana,Gakovic, Andrea,Kojic, Vesna,Bogdanovic, Gordana,Klisuric, Olivera,Gasi, Katarina Penov
experimental part, (2011/05/11)
Starting from methyl salicylate and 2-amino-2-(hydroxymethyl)propane-1,3- diol 1a, or 2-amino- 2-methylpropane-1-ol 1b, the 2-oxazoline derivatives 2a, 2b or 3, as well as mono- 4a and 4b and bis- 5a and 5b derivatives of salicylic acid were synthesized. Reactions were performed by microwave irradiation in the presence of tetrabutylammonium bromide or metallic sodium as catalyst, as well as by conventional heating. Microwave-induced reaction of some diols, diamines and amino alcohols with methyl salicylate gave mono- and/or bis- derivatives of salicylic acid 4c, 5c, 5d, 6c, 8c, 7a, 7b, 8a and 8b. The mono- and bis-salicyloyl derivatives 4c, 5c and 5d were transformed to the corresponding phenyl-azo derivatives 9, 10c and 10d. The structure of compound 3 was proved by the X-ray analysis and the R-configuration on its stereocenter was confirmed. The antioxidant and cytotoxic activities of the synthesized derivatives were evaluated in a series of in vitro tests. Compounds 5d, 8b and 8c exhibited very strong activity against hydroxyl radical. Six 4c, 5d, 8a-c, 10c of 16 tested compounds inhibited growth of MDA-MB-231 cells at a nanomolar concentration. Compounds 8c and 10c showed high cytotoxicity against MCF7 cells, whereas compounds 4c, 5d, 8a-c and 10d showed high activity against K562 cells. ARKAT-USA, Inc.
Three isomeric forms of hydroxyphenyl-2-oxazoline: 2-(2-hydroxyphenyl)-2- oxazoline, 2-(3-hydroxyphenyl)-2-oxazoline and 2-(4-hydroxyphenyl)-2-oxazoline
Langer, Vratislav,Koos, Miroslav,Gyepesova, Dalma,Sladkovicova, Mariana,Luston, Jozef,Kronek, Juraj
, p. o602-o606 (2007/10/03)
Crystal structures are reported for three isomeric compounds, namely 2-(2-hydroxyphenyl)-2-oxazoline, (I), 2-(3-hydroxyphenyl)-2-oxazoline, (II), and 2-(4-hydroxyphenyl)-2-oxazoline, (III), all C9H9NO 2 [systematic names: 2-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (I), 3-(4,5-dihydro-1,3-oxazol-2-yl)phenol, (II), and 4-(4,5-dihydro-1,3-oxazol-2-yl) phenol, (III)]. In these compounds, the deviation from coplanarity of the oxazoline and benzene rings is dependent on the position of the hydroxy group on the benzene ring. The coplanar arrangement in (I) is stabilized by a strong intramolecular O-H...N hydrogen bond. Surprisingly, the 2-oxazoline ring in molecule B of (II) adopts a 3T4 (C2T C3) conformation, while the 2-oxazoline ring in molecule A, as well as that in (I) and (III), is nearly planar, as expected. Tetramers of molecules of (II) are formed and they are bound together via weak C-H...N hydrogen bonds. In (III), strong intermolecular O-H...N hydrogen bonds and weak intramolecular C-H...O hydrogen bonds lead to the formation of an infinite chain of molecules perpendicular to the b direction. This paper also reports a theoretical investigation of hydrogen bonds, based on density functional theory (DFT) employing periodic boundary conditions.
Effects of mixed H2O-CH3CN solvents on the Bronsted coefficient for the intramolecular general base-catalyzed cleavage of ionized phenyl salicylate in the presence of primary and secondary amines
Khan, M. Niyaz,Arifin,George,Wahab
, p. 153 - 164 (2007/10/03)
Nucleophilic second-order rate constants, knms, for the reactions of several primary and secondary amines with ionized phenyl salicylate (PS-) show a nonlinear decrease with the increase in the content of CH3CN from 2 to ≤50% v/v in mixed aqueous solvent. The values of knms remain almost unchanged with the change in the content of CH3CN at >50% v/v. The nucleophilic reactivity of primary and secondary amines toward PS- reveal Bronsted plots of different Bronsted coefficients, βnuc, at a constant content of CH3CN in mixed aqueous solvents. The values of βnuc decrease from 0.4 to nearly 0 for primary amines and from 0.22 to 0.12 for secondary amines with the increase in CH3CN content from 2 to 70% v/v. The values of knms/kMeOHms (where kMeOHms represents the nucleophilic second-order rate constant for the reaction of MeOH with PS- in H2O-CH3CN solvents), obtained within 2-50% v/v CH3CN, fit to an empirical equation: log (knms/kMeOHms) = θ+λX where X is the % v/v content of CH3CN, and θ and λ are empirical constants. It has been shown empirically that both θ and λ are the function of Bronsted coefficient βlg. The values of λ are used to calculate βlg and these βlg values for all amines except Tris lie within -0.32 to -0.46. The effects of mixed water-acetonitrile solvents on pKa of leaving the group, phenol, and conjugate acid of amine nucleophile have been concluded to be the major source for the observed solvent effects on knms. The βlg for Tris is unusually very close to zero.
