65896-28-8Relevant academic research and scientific papers
A novel ruthenium (II) polypyridyl complex bearing 1,8-naphthyridine as a high selectivity and sensitivity fluorescent chemosensor for Cu2+ and Fe3+ ions
He, Chixian,Yu, Shiwen,Ma, Shuye,Liu, Zining,Yao, Lifeng,Cheng, Feixiang,Liu, Pinhua
, (2019)
A novel ruthenium(II) polypyridyl complex bearing 1,8-naphthyridine was successfully designed and synthesized. This complex was fully characterized by EI-HRMS, NMR, and elemental analyses. The recognition properties of the complex for various metal ions were investigated. The results suggested that the complex displayed high selectivity and sensitivity for Cu2+ and Fe3+ ions with good anti-interference in the CH3CN/H2O (1:1, v/v) solution. The fluorescent chemosensor showed obvious fluorescence quenching when the Cu2+ and Fe3+ ions were added. The detection limits of Cu2+ and Fe3+ were 39.9 nmol/L and 6.68 nmol/L, respectively. This study suggested that this Ru(II) polypyridyl complex can be used as a high selectivity and sensitivity fluorescent chemosensor for Cu2+ and Fe3+ ions.
Iron-Catalyzed Water Oxidation: O–O Bond Formation via Intramolecular Oxo–Oxo Interaction
Liao, Rong-Zhen,Su, Xiao-Jun,Xie, Fei,Zhang, Hong-Tao,Zhang, Ming-Tian
supporting information, p. 12467 - 12474 (2021/05/06)
Herein, we report the importance of structure regulation on the O?O bond formation process in binuclear iron catalysts. Three complexes, [Fe2(μ-O)(OH2)2(TPA)2]4+ (1), [Fe2(μ-O)(OH2)2(6-HPA)]4+ (2) and [Fe2(μ-O)(OH2)2(BPMAN)]4+ (3), have been designed as electrocatalysts for water oxidation in 0.1 M NaHCO3 solution (pH 8.4). We found that 1 and 2 are molecular catalysts and that O?O bond formation proceeds via oxo–oxo coupling rather than by the water nucleophilic attack (WNA) pathway. In contrast, complex 3 displays negligible catalytic activity. DFT calculations suggested that the anti to syn isomerization of the two high-valent Fe=O moieties in these catalysts takes place via the axial rotation of one Fe=O unit around the Fe-O-Fe center. This is followed by the O?O bond formation via an oxo–oxo coupling pathway at the FeIVFeIV state or via oxo–oxyl coupling pathway at the FeIVFeV state. Importantly, the rigid BPMAN ligand in complex 3 limits the anti to syn isomerization and axial rotation of the Fe=O moiety, which accounts for the negligible catalytic activity.
Rigid chelating dicarbene ligands based on naphthyridine-fused bisimidazolium salts
Gao, Ge,Liu, Yan,She, Zhijie,Wang, Tianbao,Zheng, Qinze,Zheng, Xuesong
supporting information, (2021/11/26)
Naphthyridine-fused bisimidazolium salts were designed and synthesized for the first time. The study of the Cu(II) and Pd(II) complexes demonstrated that the deprotonated dicarbene ligands are rigid chelating C,C-ligands with strong electron-donating ability in analogy with the classic phenanthroline N,N-ligands.
C2-Symmetric Dinickel Catalysts for Enantioselective [4 + 1]-Cycloadditions
Behlen, Michael J.,Uyeda, Christopher
supporting information, p. 17294 - 17300 (2020/11/13)
Dinickel naphthyridine-bis(oxazoline) catalysts promote enantioselective intermolecular [4 + 1]-cycloadditions of vinylidene equivalents and 1,3-dienes. The products of this reaction are methylenecyclopentenes, and the exocyclic alkene is generally obtained with high Z selectivity. E- and Z-dienes react in a stereoconvergent fashion, providing cycloadducts with the same sense of absolute stereochemistry and nearly identical ee values. This feature allows dienes that are commercially available as E/Z mixtures to be used as substrates for the cycloaddition. A DFT model for the origin of asymmetric induction is provided.
Microwave Assisted Improved Synthesis of 6-Formylpterin and Other Heterocyclic Mono- and Di-aldehydes
Goswami, Shyamaprosad,Adak, Avijit Kumar
, p. 475 - 480 (2007/10/03)
2-Pivaloylamino-6-formylpterin (1a) and a series of other important heterocyclic aldehydes (2a, 3a, 4a, 6a, and 7a) have been synthesized in good yield by microwave assisted selenium dioxide oxidation. Interestingly, 2-methylpyrazine gives 2-pyrazinecarboxylic acid (5a) under the similar condition.
Elaboration of 1,8-naphthyridine-2,7-dicarboxaldehyde into novel 2,7-dimethylimine derivatives
Vu, Choua,Walker, DeeDee,Wells, Jason,Fox, Stephen
, p. 829 - 832 (2007/10/03)
The known 1,8-naphthyridine-2,7-dicarboxaldehyde was prepared by SeO2 oxidation of 2,7-dimethyl-1,8-naphthyridine. The dimethylated naphthyridine molecule was assembled from an adaptation of the Skraup synthesis using 2-amino-6-methylpyridine and crotonaldehyde to afford a reproducible 37% yield, and constitute a significant advance over the literature of this reaction. The condensation of 1,8-naphthyridine-2,7-dicarboxaldehyde with various primary amines (R = -C6H11, -CH2C6H5, -C(CH3)3, -C10H15, and CH2CH2SCH2CH3) in alcohol affords diimines l(a-e). The inherent crystallinity of 1(a-e) affords pure compounds in reasonable to excellent yields (ca. 70%) after evaporation of solvent and recrystallization. The anticipated spectroscopic features of (N=C-H) 1H nmr shift and v(C=N) in the ir spectrum appear around 8.50 δ and 1640 cm-1, respectively, for the series 1(a-e). These novel naphthyridines typically display the signature 1H nmr doublets at ca. 8.15-8.30 δ ascribed to the 3 and 4 naphthyridine protons, consistent with a mirror plane (through the quaternary carbons) perpendicular to the naphthyridine plane, and syn, syn relationships of the naphthyridine moiety with each imine nitrogen lone pair. Complexation studies of 1(a-e) with transition metals of biological relevance such as copper(I) and copper(II) will be reported elsewhere.
Design and synthesis of multidentate dinucleating ligands based on 1,8-naphthyridine
He, Chuan,Lippard, Stephen J
, p. 8245 - 8252 (2007/10/03)
Several novel multidentate dinucleating ligands based on 1,8-naphthyridine have been synthesized in which the 1,8-naphthyridine moiety serves as a bridging unit. These ligands can link two metal ions like the syn, syn coordination mode of bridging carboxylate groups encountered in a variety of dimetallic centers in biology. Stable dimetallic complexes with variable metal-metal separations and geometries readily form with the use of these ligands. (C) 2000 Elsevier Science Ltd.
The Synthesis of Macrocyclic Polyether-Diesters Incorporating 1,10-Phenanthrolino and 1,8-Naphthyridino Subunits
Chandler, Christopher J.,Deady, Leslie W.,Reiss, James A.,Tzimos, Vasilios
, p. 1017 - 1019 (2007/10/02)
The preparation of a series of macrocycles, formed by reaction of HO-(-CH2-CH2-O-)nH with 1,10-phenanthroline-2,9-dicarbonyl chloride (n=2,3,4) and 1,8-naphthyridine-2,7-dicarbonyl chloride (n=3,4), is described.An improved synthetic route to 2,7-dimethyl-1,8-naphthyridine 9 is also reported.
