The synthesis of macrocyclic polyether‐diesters incorporating 1,10‐phenanthrolino and 1,8‐naphthyridino subunits

Chandler, Christopher J.; Deady, Leslie W.; Reiss, J. A.; TZIMOS, V.

doi:10.1002/jhet.5570190507

Cited by 75 publications

(54 citation statements)

References 16 publications

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“…The 2,6-bis(bromomethyl)pyridine [5] (3a; from la), 6,6'-bis(bromomethyl)-2,2'-bipyridine (3e; from le) (61, 1,1'-bis(bromomethyl)-3,3'-biisoquinoline (3f; from If) [7], 2,2'-dimethyl-4,4-bipyrimidine (li) [S], and 2,7-dimethyl-l,S-naphthyridine (lj) [9] were prepared as reported in the literature.…”

mentioning

confidence: 99%

New Heteroaromatic Complexing Agents and Luminescence of Their Europium(III) and Terbium(III) Chelates

Mukkala

Sund

Kwiatkowski

et al. 1992

Helvetica Chimica Acta

108

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Twelve heteroaromatic complexing agents 9a-1 were synthesized with the purpose to develop suitable labels for time-resolved luminescence-based bioaffinity assays. The relative luminescence yields, excitation maxima, and emission decay constants of their europium(II1) and terbium(lI1) chelates were determined. According to these results, 2,2',2",2"'-[(2,2'-bipyridine-6,6'-diyl)bis(methylenenitrilo)]tetrakis(acetic acid) (9e) and 2,2,2,2-[(2,2': 6',2"-terpyridine-6,6"-diyl)bis(methylenenitrilo)]tetrakis(a~tic acid) (91) are the most promising agents.Introduction. -Luminescent and fluorescent probes were the subject of intensive research during the last years. The most used fluorescent probes have such a short decay time that it is difficult to separate their fluorescence from the background and the scatterings of the sample [ 11. The long-lived luminescence characteristic of certain rareearth chelates was known for a long time [2]. These rare-earth chelates possess narrow emission bands and a large difference between the excitation and emission wavelengths, which can be exploited to decrease the interference caused by the background and the scatterings [ 11.General requirements for luminescent lanthanide chelates to be used as labels in immunoassays are the high quantum yield of the emission, high kinetic stability, good H,O solubility, and the existence of a functional group for covalent coupling to an antigen or antibody. Moreover, the coupling process should neither decrease the immunoreactivity of the labeled substances nor increase its unspecific binding to plastics etc. The chelates generally comprise a central metal ion and a chromophore, playing numerous roles in the complex. The chromophore absorbs light and transfers the excitation energy to the lanthanide ion. Furthermore, it shields the lanthanide ion from the interaction with H,O molecules, which would otherwise cause nonradiative deactivation of the excited state.

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mentioning

confidence: 99%

New Heteroaromatic Complexing Agents and Luminescence of Their Europium(III) and Terbium(III) Chelates

Mukkala

Sund

Kwiatkowski

et al. 1992

Helvetica Chimica Acta

108

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“…From this crude compound was sublimed (at 18 mm Hg, 125°) beautiful white needles of product (9.66 g, 37%). Alternatively, the crude compound could be dissolved in hot cyclohexane, filtered, allowed to cool, collected and dried to again give a white crystalline product, in comparable yield; mp 193-195°; ir This compound was prepared with minor modification according to the report of Chandler and co-workers [2]. To a stirring refluxing mixture of selenium dioxide (22.50 g, 202.8 mmol), 1,4-dioxan (750 mL) and 4 Å molecular sieves (5.50g), in 2 L three-necked, round bottom flask was added 2,7-dimethyl-1,8-naphthyridine (10.00 g, 63.2 mmol) via funnel.…”

Section: Methodsmentioning

confidence: 99%

“…This preparation, presumably that of nitrobenzenesulfonic acid, was adapted from several previous reports [2,3]: in a 1.00 L three-necked flask equipped with a stir bar was charged 30% oleum (230.0 g, 861.6 mmol) and at a steady temperature of 25°w as added nitrobenzene (52.6 g, 427.3 mmol) over a 30 minute period. Stirring was maintained at ca.…”

Section: Methodsmentioning

confidence: 99%

“…We prepared 1,8-naphthyridine-2,7-dicarboxaldehyde from 2,7-dimethyl-1,8-naphthyridine in ca. 60% yield, following the selenium dioxide protocol of Chandler and co-workers [2]. The dimethyl compound was generated from an adaptation of the Skraup synthesis, adapted by Good and coworkers, which we modified to improve the reported yield to ca.…”

Section: Introductionmentioning

confidence: 99%

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Elaboration of 1,8‐naphthyridine‐2,7‐dicarboxaldehyde into novel 2,7‐dimethylimine derivatives

Walker

Wells

et al. 2002

Journal of Heterocyclic Chem

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The known 1,8-naphthyridine-2,7-dicarboxaldehyde was prepared by SeO 2 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 = -C 6 H 11 , -CH 2 C 6 H 5 , -C(CH 3 ) 3 , -C 10 H 15 , and CH 2 CH 2 SCH 2 CH 3 ) in alcohol affords diimines 1(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) 1 H nmr shift and ν(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 1 H 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.

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“…Moreover the properties of the donor atoms in the heterocycle can easily be modified by substitution in the aromatic rings, and these derivatives can also be chromo-or fluorogenic, making them effective optical sensor molecules. Synthesis and molecular recognition studies of many crown ethers based on tricyclic heterocycles are reported in the literature, for example those of xanthone 10 -, dibenzofuran [11][12][13][14] -, phenanthroline [15][16][17][18][19][20][21][22] -, phenazine [23][24][25][26][27] -, or acridone-and acridine 23,[28][29][30][31][32][33][34][35][36][37] -based macrocycles. In the continuation of our research of crown ethers based on tricyclic ring systems, [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] our attention turned toward phenothiazine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel 18-crown-6 type ligands containing a phenothiazine 5,5-dioxide unit

Kormos¹,

Sveiczer²,

Fődi³

et al. 2013

Arkivoc

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The synthesis of macrocyclic polyether‐diesters incorporating 1,10‐phenanthrolino and 1,8‐naphthyridino subunits

Cited by 75 publications

References 16 publications

New Heteroaromatic Complexing Agents and Luminescence of Their Europium(III) and Terbium(III) Chelates

New Heteroaromatic Complexing Agents and Luminescence of Their Europium(III) and Terbium(III) Chelates

Elaboration of 1,8‐naphthyridine‐2,7‐dicarboxaldehyde into novel 2,7‐dimethylimine derivatives

Synthesis of novel 18-crown-6 type ligands containing a phenothiazine 5,5-dioxide unit

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