Synthesis of New Pyridinoazacrown Ethers Containing Aromatic and Heteroaromatic Proton Ionizable Substituents

Bordunov, Andrei V.; Hellier, Paul C.; Bradshaw, Jerald S.; Dalley, N. Kent; Kou, Xiaolan; Zhang, Xian Xin; Izatt, Reed M.

doi:10.1021/jo00124a022

Cited by 45 publications

(33 citation statements)

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“…Reduction of the dinitro functionalities afforded the corresponding air-sensitive diamines (16؊19), which were used directly in the final quinoxalineproducing step. This step involved reaction of 1,2-bis(1H-pyrrol-2-yl)ethanedione (20) amine 16؊19 in an approximately 1:1 mixture of EtOH and acetic acid, under reflux conditions. This produced the ''crowned'' dipyrrolylquinoxalines 1Ϫ4 in moderate to quantitative yields (49Ϫ100%) (Scheme 2).…”

Section: Synthesismentioning

confidence: 99%

Synthesis, Structural Characterization and Complexation Properties of the First “Crowned” Dipyrrolylquinoxalines

et al. 2002

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Section: Synthesismentioning

confidence: 99%

Synthesis, Structural Characterization and Complexation Properties of the First “Crowned” Dipyrrolylquinoxalines

et al. 2002

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“…11 The synthetic procedures for 3-6 are represented in the Supporting Information. L was prepared by the reaction of 6 and 9-chloromethylanthracene in CH 3 CN in the presence of K 2 CO 3 and KI under reflux condition.…”

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Synthesis, Complexation and Fluorescence Properties of N-Anthracenylmethyl Dipodal Ligand with Quinoline End-Group

Kang¹,

Moon

Park³

et al. 2007

Bulletin of the Korean Chemical Society

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Recently, many efforts have been devoted to design and construction of fluorescent chemosensors that are capable of detecting metal ions. [1][2][3][4][5] In many cases, the fluorescent chemosensors have been made through the combination of a receptor molecule and a fluorophore. Owing to their selective complexation with metal species, macrocyclic ligands make them ideal candidates for the receptor molecules. However, the introduction of such cyclic receptors is often limited by high cost and the synthetic complexity. The alternate way to avoid such limitations is to develop the acyclic analogues for the cyclic receptors. Our interest has focused on the dipodal receptors containing quinoline moiety because this receptor has shown not only similar behaviors with cyclic receptors, 6,7 and the unique coordination ability for some transition metal ions 8,9 but also been synthesized easily in high yields. 10 Recently, we reported the unique pseudo-cyclic Cd(II) complexes, in which the dipodal receptor with quinoline end-groups wraps around the cadmium atom in a helical manner. 9 In connection with this reason, we have synthesized N-anthracenylmethyl dipodal receptor (L) with quinoline end-groups and have further carried out the exploration of its complexation and metal-induced fluorescence properties.In the synthesis of L (see Scheme 1), the starting material 2 was prepared as previously reported.11 The synthetic procedures for 3-6 are represented in the Supporting Information. L was prepared by the reaction of 6 and 9-chloromethylanthracene in CH 3 CN in the presence of K 2 CO 3 and KI under reflux condition. Purification by column chromatography afforded L as a yellow oil in 63% yield. This ligand was fully characterized by conventional methods.The photophysical properties of L were measured in CH 3 CN. In fluorescent spectrum of free L, upon excitation at 367 nm, typical emission bands from anthracene moiety were observed at 399, 419 and 442 nm. The quantum yield of fluorescence was determined as ca. 0.10 using 9-methylanthracene (0.284) as a reference compound. This fact would imply that quenching occurs in L, which might suggest that there was an effective quenching of the excited state of fluorophore by the receptor moiety, via photoinduced electron transfer (PET) before addition of metal ions (prior to metal ion recognition). Scheme 1. Synthesis of the dipodal fluorophore L.

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“…3,4 For synthesis of such phenolic azacrown compounds, Bradshaw group has found one-step method based on Mannich reaction for which N-(methoxymethyl)azacrown and appropriate phenols were used. 5 Compared with the alkylation of azacrown ethers with 2-hydroxybenzyl halide, this Mannich reaction has at least two advantages: (i) the substituted phenols are readily available and (ii) due to the electrophilic character of the reaction it is not necessary to protect the functional groups of the substituted phenols, sensitive to nucleophilic attack by the azacrown ether nitrogen. 5 Lagow recently also reported one-pot synthesis using 1,10-diaza-18-crown-6 and parasubstituted phenol in the presence of paraformaldehyde to give the Mannich reaction product.…”

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confidence: 99%

“…5 Compared with the alkylation of azacrown ethers with 2-hydroxybenzyl halide, this Mannich reaction has at least two advantages: (i) the substituted phenols are readily available and (ii) due to the electrophilic character of the reaction it is not necessary to protect the functional groups of the substituted phenols, sensitive to nucleophilic attack by the azacrown ether nitrogen. 5 Lagow recently also reported one-pot synthesis using 1,10-diaza-18-crown-6 and parasubstituted phenol in the presence of paraformaldehyde to give the Mannich reaction product. 6 Recently, we have been intrigued by the synthesis of ditopic receptor that is defined with bis-calixazacrown molecule capable of binding two guest ions in the azacrown cavity.…”

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confidence: 99%

Proton-diionizable Bis-calix[4]azacrown Ether through Mannich Reaction

Kim

Lee

et al. 2002

Bulletin of the Korean Chemical Society

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Synthesis of New Pyridinoazacrown Ethers Containing Aromatic and Heteroaromatic Proton Ionizable Substituents

Cited by 45 publications

References 1 publication

Synthesis, Structural Characterization and Complexation Properties of the First “Crowned” Dipyrrolylquinoxalines

Synthesis, Structural Characterization and Complexation Properties of the First “Crowned” Dipyrrolylquinoxalines

Synthesis, Complexation and Fluorescence Properties of N-Anthracenylmethyl Dipodal Ligand with Quinoline End-Group

Proton-diionizable Bis-calix[4]azacrown Ether through Mannich Reaction

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