Synthetic, spectroscopic, and computational investigations of readily accessible 2‐phenyl‐3‐alkylbenzoxazaboroles

Rathnayaka, R. M. Chathurika; George, Sobiya; Abeysinghe, Janaka P.; Lynch, Vincent M.; Gross, Dustin E.

doi:10.1002/jhet.4442

Cited by 2 publications

(2 citation statements)

References 27 publications

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“…The carbon C 23 containing the group OH gave a signal at 136.648 ppm [21], while the carbon C 9 gave the signal at 116.476 ppm due to thiazole [22]. Where the following carbon atoms C 3 -C 4 -C 10 -C 22 gave values between 129.092-131.752 ppm due to the connection of carbon atoms with nitrogen atoms [23][24]. As for these two signals at 144.818-141.912 ppm, C 1 -C 2 is due to the two groups of azomethane (-C=N-) [25].…”

Section: The 13 C-nmr Spectrum Of the Ligand (Dptyeap)mentioning

confidence: 99%

Synthesis of a New DPTYEAP Ligand and Its Complexes with Their Assessments on Physical Properties, Antioxidant, and Biological Potential to Treat Breast Cancer

Yasir

Jamel

2023

Indones. J. Chem.

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A new series of complexes of the 2-((1E,2E)-1,2-diphenyl-2-(thiazol-2-ylimino)ethylidene)amino)phenol (DPTYEAP) has been synthesized by the reaction of the ligand with metal chlorides of Ni(II), Cu(II), Pt(IV), and AgNO3 in ethanol as a solvent. The ligand was prepared for the two steps. In the first step, compound (A) was synthesized by reacting 2-aminothiazol with benzil in ethanol. Another step is the preparation of the ligand from the reaction of compound (A) with 2-aminophenol. The structures of the ligand and its complexes were confirmed by FTIR, 1H-13C-NMR, UV-Vis spectra, melting points, molar conductivity (C, H, and N), and magnetic susceptibility. The synthesized complexes were prepared in a 1:2 ratio for Ni(II), Cu(II), and Pt(IV) complexes and a 1:1 ratio (M:L) for Ag(I) complexes. The geometric shape of all complexes is octahedral, except for the Ag(I) complex, which is tetrahedral. The antioxidant test for the prepared compounds was carried out. The anticancer test was conducted for each of the ligands and the platinum(IV) complex, and it was found that the platinum complex is more effective against breast cancer cells (MCF-7); thus, it can be used as a potential drug after studying it well.

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Section: The 13 C-nmr Spectrum Of the Ligand (Dptyeap)mentioning

confidence: 99%

Synthesis of a New DPTYEAP Ligand and Its Complexes with Their Assessments on Physical Properties, Antioxidant, and Biological Potential to Treat Breast Cancer

Yasir

Jamel

2023

Indones. J. Chem.

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“…Aminophenols are common organic building blocks in the preparation of nitrogen- and oxygen-containing heterocycles. , They are also potent neuroprotective agents . The 1-(2-pyrrolyl)alkylamine scaffold is a common structural unit in a series of terpene indole alkaloids and noncinchona indole alkaloids.…”

Section: Introductionmentioning

confidence: 99%

Octalithium, Tetrasodium, and Decalithium Compounds Based on Pyrrolyl Ligands: Synthesis, Structures, and Activation of the C–H Bonds of Pyrrolyl Rings and C═N Bonds of a Series of Ligands by Organolithium Reagents

Jia

She

et al. 2023

Inorg. Chem.

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The organometallic compounds of lithium ions have garnered continuous interest as indispensable precursors for the syntheses of organometallic complexes of main-group metals, transition metals, lanthanide metals, and actinide metals. In this work, we present a strategy for the preparation of a series of polynuclear lithium complexes. This methodology features the utilization of organolithium reagents both as metal sources to coordinate with the ligands and as nucleophilic reagents to undergo nucleophilic addition to the C�N bonds of the ligands. Reaction of a ligand HL1amino)phenol]. One prominent feature regarding the formation of 1•1.5Tol is the occurrence of nucleophilic addition of n-BuLi to the C�N bond of HL1, leading to the generation of a new [L1a] 2− ligand that contains both aminophenol and 1-(2-pyrrolyl)alkylamine scaffolds. The developed protocol can be adapted to a series of organolithium reagents. Compounds [Li 8 (L1b) 4 ] (2) and [Li 8 (L1c) 4 ] (3) were afforded by treatment of HL1 with sec-BuLi and LiCH 2 SiMe 3 , respectively. Reaction of an analogous ligand HL2 [HL2 = 2-(((1-(2-(dimethylamino)ethyl)-1H-pyrrol-2yl)methylene)amino)-4-methylphenol] with n-BuLi generated compound [Li 8 (L2a) 4 ] ( 4). C�N bond activation was not observed in the reaction of HL1 with NaO t Bu, and the complex [Na 4 (L1) 4 ]•Tol (5•Tol) was obtained. A decanuclear complex [Li 10 (L3a) 2 (L3b) 2 ] (6) was also prepared via the reaction of HL3 [HL3 = 2-(2-((((1H-pyrrol-2-yl)methylene)amino)methyl)-1Hpyrrol-1-yl)-N,N-dimethylethan-1-amine] with t-BuLi. A remarkable feature in terms of the synthesis of 6 is the simultaneous occurrence of hydrogen atom abstraction from the C−H bond of the pyrrolyl ring and nucleophilic addition to the C�N bond of the HL3 ligand by t-BuLi. A series of amines containing biologically and physiologically important moieties were achieved by hydrolysis of the crude products from the reactions of the HL1−HL3 ligands and organolithium reagents. This work provides an efficient approach to high-nuclearity lithium compounds as well as a series of amines.

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Synthetic, spectroscopic, and computational investigations of readily accessible 2‐phenyl‐3‐alkylbenzoxazaboroles

Cited by 2 publications

References 27 publications

Synthesis of a New DPTYEAP Ligand and Its Complexes with Their Assessments on Physical Properties, Antioxidant, and Biological Potential to Treat Breast Cancer

Synthesis of a New DPTYEAP Ligand and Its Complexes with Their Assessments on Physical Properties, Antioxidant, and Biological Potential to Treat Breast Cancer

Octalithium, Tetrasodium, and Decalithium Compounds Based on Pyrrolyl Ligands: Synthesis, Structures, and Activation of the C–H Bonds of Pyrrolyl Rings and C═N Bonds of a Series of Ligands by Organolithium Reagents

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