840-57-3Relevant academic research and scientific papers
Synthesis, Characterization and DFT-D Studies of 2-Aminoethoxycalix[4]resorcinarenes: A Novel Heterogeneous Organocatalyst
Hiba, K.,Shaibuna, M.,Shebitha, A. M.,Sreekumar, K.
, (2022/01/12)
The present article reports the synthesis of two novel supramolecular architectures, Phenyl(octa-2-aminoethoxy)calix[4]resorcinarene and 2-Aminoethoxyphenyl-(octa-2-aminoethoxy)calix[4]resorcinarene via surface functionalization and describes their applic
Phosphine-phosphonium ylides as ligands in palladium-catalysed C2-H arylation of benzoxazoles
Yao, Zhenyu,Lin, Xing,Chauvin, Remi,Wang, Lianhui,Gras, Emmanuel,Cui, Xiuling
, p. 3250 - 3254 (2020/05/25)
As balanced electron-rich P,C-chelating ligands, phosphine-phosphonium-ylides are considered for their ability to in situ promote palladium-catalysed direct C(sp2)–H arylation. Using methyl phosphonium salts of 2,2'-bis(diphenylphosphino)-1,1'-binaphtyl (“methyl-BINAPIUM”) as ylide precursors under optimized reaction conditions, arylation of benzoxazole was found to proceed in moderate to high yield to give functional 2-aryl benzoxazoles. A strong anion effect of the non-salt free ylide was evidenced (TfO? > I? > PF6? ≈ salt-free). This first example of phosphonium ylides as ligands in catalytic C–H activation extends the prospect of their general implementation in homogeneous transition metal catalysis.
Development of homogeneous polyamine organocatalyst for the synthesis of 2-aryl-substituted benzimidazole and benzoxazole derivatives
Kottayil, Hiba,Machingal, Shaibuna,Parackal B., Sherly mole,Alungal M., Shebitha,Theresa, Letcy V.,Govindan, Avudaiappan,Krishnapillai, Sreekumar
, p. 3310 - 3317 (2020/07/17)
A new polyamine was prepared by the ring opening polymerization of epichlorohydrin and properly characterized. The catalytic property of the prepared polymer was assessed by synthesizing 2-aryl-substituted benzimidazole and benzoxazole derivatives by the conjugation of o-phenylenediamine/o-aminophenol with various aromatic aldehydes in the presence of atmospheric oxygen. Significant attributes of the present synthesis include short reaction time, good to excellent yield, high purity, easy reusability, and room temperature reaction. The reaction was carried out in the absence of any metal catalyst and other cooxidants.
In-vitro Anti-cancer assay and apoptotic cell pathway of newly synthesized benzoxazole-N-heterocyclic hybrids as potent tyrosine kinase inhibitors
Desai, Sulaksha,Desai, Vidya,Shingade, Sunil
supporting information, (2019/11/13)
A series of benzoxazole-N-heterocyclic hybrids have been synthesized by a one-pot strategy. Molecular docking study revealed that such compounds have the ability to inhibit enzyme protein tyrosine kinase. The findings of this work have been the successful synthesis of benzoxazole scaffolds, featuring hybrids of benzoxazole with quinoline and quinoxaline respectively. The molecular docking studies have showed these compounds to be inhibitors of tyrosine kinase enzyme which triggers growth of cancer cells. The cytotoxicity study of compounds 4a-f showed better potency against breast cancer cell lines MCF-7 and MDA-MB-231 in contrast to oral and lung cancer cell lines KB and A549. The tyrosine kinase activity was measured using Universal Tyrosine Kinase Assay kit using horseradish peroxide (HRP)-conjugated anti-phosphotyrosine kinase solution as a substrate. The compounds 4c exhibited maximum inhibition in the activity of enzyme tyrosine kinase with IC50 value 0.10 ± 0.16 μM, than other compounds which were studied and thus proved to be inhibitors of enzyme tyrosine kinase. The selective index of all four compounds was found out to be greater than two, indicating the non-toxic behaviour, i.e. good anti-cancer activity. Further, fluorescence microscopic study helped to characterize the mode of cell death, which was found to be late apoptosis as indicated by the orange fluorescence. The SAR analysis has also been carried out.
Pd/Cu bimetallic co-catalyzed direct 2-arylation of benzoxazole with aryl chloride
Zheng, Ling-Li,Yin, Bo,Tian, Xing-Chuan,Yuan, Ming-Yong,Li, Xiao-Huan,Gao, Feng
supporting information, (2019/11/13)
An efficient Palladium/Copper bimetallic co-catalyzed direct 2-arylation of benzoxazoles with aryl chlorides is presented. The Pd(OAc)2/CuI/NiXantphos-based catalyst enables the installation of various aryl and heteroaryl groups in good to excellent yields (75–99%). Preliminary mechanism investigation indicates that Pd/Nixantphos complex activates C-Cl bond of aryl chlorides via oxidative addition, and Cu/Nixantphos complex chelates with nitrogen atom to lower the pKa of the 2-H in benzoxazoles.
Oxidative NHC Catalysis for the Generation of Imidoyl Azoliums: Synthesis of Benzoxazoles
Patra, Atanu,James, Anjima,Das, Tamal Kanti,Biju, Akkattu T.
, p. 14820 - 14826 (2019/01/03)
N-Heterocyclic carbene (NHC)-catalyzed intramolecular cyclization of aldimines generated from 2-amino phenols and aromatic aldehydes leading to the synthesis of 2-arylbenzoxazoles under mild conditions is presented. The reaction proceeds via the generation of the aza-Breslow intermediates from imines and NHC, which under oxidative conditions form the key imidoyl azoliums and a subsequent intramolecular cyclization furnishes the product. The reaction tolerates a broad range of functional groups, and the products are formed in generally good yields.
Ni-Catalyzed C?F Bond Functionalization of Unactivated Aryl Fluorides and Corresponding Coupling with Oxazoles
Yin, Youzhi,Yue, Xiaoyu,Zhong, Qi,Jiang, Hanmin,Bai, Ruopeng,Lan, Yu,Zhang, Hua
supporting information, p. 1639 - 1643 (2018/03/21)
A Ni-catalyzed C?F bond functionalization of unactivated aryl fluorides with oxazoles as coupling partners was developed. Various arylated oxazoles could be obtained in moderate to good yields in the presence of Ni(cod)2/IMes catalytic system.
Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents
Yang, Bo,Wang, Zhong-Xia
supporting information, p. 6220 - 6223 (2017/11/24)
Cross-coupling of (hetero)arylthiols with arylzinc reagents via C-S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.
Optically operated second order optical effects in some substituted 4-(5-nitro-1,3-benzoxazol-2-yl)aniline chromophores
Szlachcic,Fedorchuk,Danel,Jarosz,El Naggar,Albassam,Wojciechowski,Gondek,Uchacz,Stadnicka,Lakshminarayana,Kityk
, p. 333 - 341 (2017/03/08)
In this work, we report on second order nonlinear optical (NLO) susceptibilities of some substituted 4-(5-nitro-1,3-benzoxazol-2-yl)aniline chromophores that were embedded into photopolymer matrices. Depending on the photo-induced nitrogen laser (waveleng
Magnetic Co-doped NiFe2O4 Nanocomposite: A Heterogeneous and Recyclable Catalyst for the One-Pot Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles under Solvent-Free Conditions
Karimian, Azam,Mohammadzadeh Kakhki, Roya,Kargar Beidokhti, Hamideh
, p. 1316 - 1325 (2017/11/22)
A simple and efficient procedure for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles via the condensation of o-phenylenediamine, o-aminophenol, and o-aminothiophenol with various benzaldehydes by using magnetic Co-doped NiFe2O4 nanoparticles has been developed. This nanocatalyst has advantages such as excellent product yields, solvent-free conditions, and very short reaction times. After any experiment, the magnetic nanocatalyst could be easily separated with the aid of an external magnet and reused at least four times without any loss of its catalytic performance.
