Some γ-Substituted Benzoquinoline Derivatives<sup>1</sup>

Foster, Robert E.; Lipscomb, Robert D.; Thompson, T. J.; Hamilton, Cliff S.

doi:10.1021/ja01211a070

Cited by 12 publications

(3 citation statements)

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“…4-Tolyl-6-phenylpicolinic acid (tppicH 2 ) 31 and 2,6-di(2-thienyl)pyridine (dthpyH 2 ) were prepared according to procedures reported previously. 4-Hydroxybenzo[ h ]quinoline-2-carboxylic acid (hbqcH 2 ) was supplied by Avecia Ltd. as the ethyl ester, and hydrolyzed to the acid using 5% NaOH(aq) at reflux. The synthesis and characterization data for 3 and 2b were reported in the Supporting Information of our previous communication …”

Section: Methodsmentioning

confidence: 99%

Luminescent Complexes of Iridium(III) Containing N∧C∧N-Coordinating Terdentate Ligands

et al. 2006

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A family of bis-terdentate iridium(III) complexes is reported which contain a cyclometalated, N/\C[wedge]N-coordinating 1,3-di(2-pyridyl)benzene derivative. This coordination mode is favored by blocking competitive cyclometalation at the C4 and C6 positions of the ligand. Thus, 1,3-di(2-pyridyl)-4,6-dimethylbenzene (dpyxH) reacts with IrCl3 x 3H2O to generate a dichlorobridged dimer [Ir(dpyx-N,C,N)Cl(mu-Cl)]2, 1. This dimer is cleaved by DMSO to give [Ir(dpyx)(DMSO)Cl2], the X-ray crystal structure of which is reported here, confirming the N/\C/\N coordination mode of dpyx. The dimer 1 can also be cleaved by a variety of other ligands to generate novel classes of mononuclear complexes. These include charge-neutral bis-terdentate complexes of the form [Ir(N/\C/\N)(C/\N/\C)] and [Ir(N/\C/\N)(C/\N/\O)], by reaction of 1 with C/\N/\C-coordinating ligands (e.g., 2,6-diphenylpyridine and derivatives) and C/\N/\O-coordinating ligands (based on 6-phenylpicolinate), respectively. Treatment of 1 with terpyridines leads to dicationic complexes of the type [Ir(N/\C/\N)(N/\N/\N)]2+, while 2-phenylpyridine gives [Ir(dpyx-N/\C/\N)(ppy-C,N)Cl]. All of the charge-neutral complexes are luminescent in fluid solution at room temperature. Assignment of the emission to charge-transfer excited states with significant MLCT character is supported by DFT calculations. In the [Ir(N/\C/\N)(C/\N/\C)] class, fluorination of the C/\N/\C ligand at the phenyl 2' and 4' positions leads to a blue-shift in the emission and to an increase in the quantum yield (lambda(max) = 547 nm, phi = 0.41 in degassed CH(3)CN at 295 K) compared to the nonfluorinated parent complex (lambda(max) = 585 nm, phi = 0.21), as well as to a stabilization of the compound with respect to photodissociation through cleavage of mutually trans Ir-C bonds. [Ir(dpyx-N/\C/\N)(ppy-C,N)Cl] is an exceptionally bright emitter: phi = 0.76, lambda(max) = 508 nm, in CH(3)CN at 295 K. In contrast, the [Ir(N/\C/\N)(C/\N/\O)] complexes are much less emissive, shown to be due to fast nonradiative decay of the excited state, probably involving reversible Ir-O bond cleavage. The [Ir(N/\C/\N)(N/\N/\N)]2+ complexes are very feeble emitters even at 77 K, probably due to the almost exclusively interligand charge-transfer nature of the lowest-energy excited state in these complexes.

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Section: Methodsmentioning

confidence: 99%

Luminescent Complexes of Iridium(III) Containing N∧C∧N-Coordinating Terdentate Ligands

et al. 2006

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“…This Gould–Jacobs-type protocol is the first reported to directly access 4-amino heterocyclic compounds in a “one-pot” fashion. These highly desirable scaffolds are otherwise generally accessed through a tedious and harsh chlorination–substitution sequence from the hydroxyl moiety of typical Gould–Jacobs products …”

Section: Resultsmentioning

confidence: 99%

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

et al. 2017

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Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.

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“…Diethyl 2-[(naphthalen-1-ylamino)methylidene]malonate (2) was synthesized by modifying a method described in the literature [23]. Ethyl 4-oxo-1,4-dihydrobenzo[h]quinoline-3-carboxylate (3) was synthesized following a published method [24].…”

Section: Methodsmentioning

confidence: 99%

Synthesis of novel 1,3,4-oxadiazole derivatives and their nucleoside analogs with antioxidant and antitumor activities

Fadda

Abdel‐Rahman

El‐Sayed³

et al. 2011

Chem Heterocycl Comp

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A series of new (1,3,4-oxadiazol-2-yl)-1H-benzo[h]quinolin-4-one derivatives were synthesized, including glucose and xylose hydrazones that were obtained by the reaction of hydrazides with monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded substituted oxadiazoline derivatives. The newly synthesized compounds were evaluated for their antioxidant properties and cytotoxicity, and showed moderate to high activities.A significant part of drug discovery efforts in the past few years has been focused on prevention or treatment of cancer. This is not surprising because in most developed countries, and to an increasing extent, cancer is among the three most common causes of death. Among the five-membered nitrogen heterocycles, 1,3,4-oxadiazoles are associated with a broad spectrum of biological activities. The 1,3,4-oxadiazole ring has been found in the structures of fungicidal, bactericidal, analgesic, antipyretic, antiphlogistic, anticompulsive, anti-inflammatory, paralytic, hypnotic, and sedative agents [1-3]. Several 1,3,4-oxadiazole derivatives have been shown to possess insecticidal, hypoglycemic, hypotensive, antiviral [4], as well as antitumor activities [5]. Certain 1,3,4-oxadiazoline-2(3H)-thiones are known to possess antibacterial, antifungal, antimicrobial, and antiviral activities [4], as well as tyrosinase-inhibiting effect [6]. Nucleosides and their analogs possess a wide range of medicinal properties, including antibiotic, antiviral, and antitumor activity [7][8][9][10][11][12][13][14][15][16]. Consequently, and considering the possible enhancement of biological activity resulting from the attachment of carbohydrate moieties to 1,3,4-oxadiazole heterocycles, our attention was turned to the synthesis of new 1,3,4-oxadiazole derivatives and their nucleoside analogs [17,18].

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Some γ-Substituted Benzoquinoline Derivatives¹

Cited by 12 publications

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Luminescent Complexes of Iridium(III) Containing N∧C∧N-Coordinating Terdentate Ligands

Luminescent Complexes of Iridium(III) Containing N∧C∧N-Coordinating Terdentate Ligands

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

Synthesis of novel 1,3,4-oxadiazole derivatives and their nucleoside analogs with antioxidant and antitumor activities

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Some γ-Substituted Benzoquinoline Derivatives1

Cited by 12 publications

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Luminescent Complexes of Iridium(III) Containing N∧C∧N-Coordinating Terdentate Ligands

Luminescent Complexes of Iridium(III) Containing N∧C∧N-Coordinating Terdentate Ligands

Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor

Synthesis of novel 1,3,4-oxadiazole derivatives and their nucleoside analogs with antioxidant and antitumor activities

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Some γ-Substituted Benzoquinoline Derivatives¹