Synthesis and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones

Tominaga, Yoshinori; Yoshioka, Noriko; Kataoka, Seigo; Shigemitsu, Yasuhiro; Hirota, Takashi; Sasaki, Kenji

doi:10.3987/com-98-s(h)20

Cited by 12 publications

(5 citation statements)

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“…This research finding triggered the development of fluorescence 2H-pyrone derivatives. [20][21][22][23][24][25][26] Scheme 1 The arrangement of suitable chromophores and auxochromes within the molecules both in the solution and solid states is necessary to confer fluorescent properties to a compound. In this respect, heterocycles synthesized using ketene dithioacetals have good substituents show fluorescence, due to ketene dithioacetals having strong electro-donating groups such as a methylsulfanyl group and strong electro-withdrawing groups such as cyano and ester groups.…”

Section: Synthesis Of 4-methylsulfanyl-2-pyrone Derivativesmentioning

confidence: 99%

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

Tominaga¹,

Mizuyama

Shigemitsu³

et al. 2009

HETEROCYCLES

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-In recent years, organic electro luminescent (EL) materials have received considerable attention due to their potential application in next-generation display devices with high brightness levels, wide color ranges, and wide viewing angles. Fluorescent 2-pyrone derivatives have been synthesized using a convenient method involving ketene dithioacetals, which emit fluorescence (red, green, and blue) in both solution (dichloromethane and ethanol) and solid state. The structure-activity relationships of various 2-pyrone derivatives have been clarified.

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Section: Synthesis Of 4-methylsulfanyl-2-pyrone Derivativesmentioning

confidence: 99%

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

Tominaga¹,

Mizuyama

Shigemitsu³

et al. 2009

HETEROCYCLES

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“…Though, there are limited reports about the construction of pyrroloquinolinediones. Mostly, they are synthesized via multistep reactions, and initiated from the substituted maleimide (Scheme 1a), [8][9] or substituted quinoline precursors (Scheme 1b). [10][11][12] Therefore, the development of effective approaches for the production of pyrroloquinolinediones from readily accessible substrates has become a significant task for synthetic chemists.…”

Section: Introductionmentioning

confidence: 99%

PhIO Mediated One‐Pot Synthesis of Pyrroloquinolinediones from ortho‐Carbonyl Anilines and Maleimides

Alahmdi,

Mukhtar,

Parveen

et al. 2024

Eur J Org Chem

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An effective, green, mild, and metal‐free hypervalent iodine‐mediated approach for the synthesis of pyrroloquinolinediones from ortho‐carbonyl anilines and maleimides in a one‐pot manner at room temperature has been developed. This proposed protocol can synthesize biologically active pyrroloquinolinediones in a one‐pot manner utilizing readily available starting materials. This protocol generates H2O as the only by‐product during the reaction and shows a high atom economy. Operational simplicity, moderate reaction conditions, high atom economy, and high yield are some key features of this protocol.

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“…Of a number of various phthalhydrazides, luminol (2-aminophthalhydrazide) is the most popular and frequently used as a chemiluminescent compound, whose noticeable feature is to act as an analytical tools by emitting light as the signal indicating the presence as well as the amount of widespread target substances such as blood for a criminal investigation (2). There have been various extensions of the phthalhydrazide chemiluminescence, many of which are structural modifications not only to enhance the emission efficiency, but also used for determination of certain chemical species (3,4). However, only a few chemiluminophores with ionophores (5,6) have been studied to date, and the potential application as a molecular recognition system is suggested.…”

Section: Introductionmentioning

confidence: 99%

Chemiluminescence of 4‐styrylphthal‐hydrazides with crown ether as ionophore

et al. 2008

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Two 4-styrylphthalhydrazides bearing crown ether moieties as ionophores were prepared and their chemiluminescence behavior was investigated. Their aerobic oxidation in the presence of excess tert-BuOK in DMSO provided the chemiluminescence with much shorter emission wavelengths than those of the corresponding phthalate dianions, indicating that the emission arose from the excited pthalates incorporated with potassium ions at the ionophore sites.Such incorporation of potassium ions with the crown sites also reduced the fluorescence intensities of the phthalate dianions which caused an energy transfer chemiluminescence, resulting in the additional emissions of the phthalhydrazide monoanions in much longer wavelength regions. On the other hand, only the emission from the excited phthalate dianion was detected under aqueous conditions using aqueous hydrogen peroxide in acetonitrile as the oxidant, but no meaningful difference in the chemiluminescence intensity depending on the kind of metal cations was observed.

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Synthesis and Chemiluminescence of 10-Hydroxy- and 10-Aminopyridazino[4,5-b]quinoline-1,4(2H,3H)-diones

Cited by 12 publications

References 0 publications

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

Development of Fluorescent 2-Pyrone Derivatives Using Ketene Dithioacetals for Organic EL Devices

PhIO Mediated One‐Pot Synthesis of Pyrroloquinolinediones from ortho‐Carbonyl Anilines and Maleimides

Chemiluminescence of 4‐styrylphthal‐hydrazides with crown ether as ionophore

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