Indigo chemiluminescence

Nikokavouras, J.; Vassilopoulos, G.

doi:10.1007/bf00904676

Cited by 5 publications

(5 citation statements)

References 6 publications

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“…This process may be involved in the fading of indigo in museum collection objects 158 and denim jeans 159,160 . The same conversion can be realized by ozonolysis 161 , acidic bromate 162 or by a chemiluminescent autoxidation of indigo 163 . N-Methylisatin is also obtained in the photooxidation of N-methylindole-3-acetic acid 164 .…”

Section: Synthesis Of Oxindoles and Dioxindolesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

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Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

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Section: Synthesis Of Oxindoles and Dioxindolesmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

860

447

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“…The outcomes of these reactions are summarized in Scheme 1. The use of the allyl bromide gave a 10% yield of the known 22 oxidative cleavage product N-allylisatin (Type A), together with the pink mono oxindolic N-allylated indirubin 9 (Type B) and the deep blue diallylindirubin 14 (Type C) in 24% and 19% yields, respectively. This initial reaction indicated that indirubin is significantly less reactive than the corresponding indigo.…”

Section: Synthesis and Product Identificationmentioning

confidence: 99%

“…22 Subsequent nucleophilic attack by allyl alcohol (formed from the bromide in the presence of carbonate) on the isatin C2-carbonyl and then addition to the C3 carbonyl, followed by fragmentation with loss of carbon dioxide and propene would give the minor anthranilate ester observed.…”

Section: Mechanistic Proposalsmentioning

confidence: 99%

A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin

et al. 2015

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. (2015). A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin. Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 71 (43), 8357-8367. A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin AbstractThe allylation of indirubin produced the expected indolic N′-allylindirubin and N,N′-diallylindirubin derivatives in moderate yields, together with the corresponding N-substituted isatin products. At higher temperatures, the base-initiated reaction with allylic halides yielded spiroindolinepyrido[1,2-a]indolediones in a one-pot cascade reaction sequence with yields of up to 70%. These readily accessed, new spiro compounds represent the first reported examples of indirubin participating in cascade reactions. Preliminary in vitro biological testing of some of the products indicated promising activity against some cancer cell lines and against Plasmodium falciparum for two spiro derivatives. Computational methods were used to gain a greater understanding of the UV/Vis spectroscopic data for the N′-substituted and N,N′-disubstituted indirubin derivatives.

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“…Chemiluminiscence of indigo solutions in polar aprotic solvents oxidised by air, ozone, hydrogen peroxide and/or potassium persulphate has been observed [10]. During this reaction indigo has once more been shown to decompose to form two molecules of isatin.…”

Section: Introductionmentioning

confidence: 98%

“…During this reaction indigo has once more been shown to decompose to form two molecules of isatin. A mechanism based on the cleavage of the central C=C group of indigo has again been suggested [10].…”

Section: Introductionmentioning

confidence: 99%

Photoegradation of indigo in dichloromethane solution

Novotná

Boon

Horst

et al. 2003

Coloration Technology

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The photodegradation of indigo has been studied with emphasis on the degradation products. Ultraviolet–visible spectrometry, high performance liquid chromatography and direct temperature‐resolved mass spectrometry were employed for the characterisation of aged samples. Indigo, isatin, isatoic anhydride, anthranilic acid and indirubin were detected, together with other unidentified compounds. A new degradation product, tryptanthrin, was identified by both high performance liquid chromatography and mass spectrometry techniques, and two other possible degradation products have also been suggested. The degradation of synthetic and natural indigo has been compared and an explanation for the higher rate of degradation of natural indigo proposed.

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Indigo chemiluminescence

Cited by 5 publications

References 6 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

A cascade synthetic route to new bioactive spiroindolinepyrido[1,2-a]indolediones from indirubin

Photoegradation of indigo in dichloromethane solution

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