Reactions of resonance stabilized carbanions. XXXI. Oxidation of carbanions. 4. Oxidation of indoxyl to indigo in basic solution

No abstract is available for this paper.

• Publication year

  1969

• Venue

  Journal of the American Chemical Society

• Publication date

  1969-07-01

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1021/JA01042A028
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• No references are available for this paper.

• A Two‐Phase Enzymatic Cascade for Indigo Synthesis from Anthranilate

  2025cites this paper
• Cytochrome P450-mediated carbon-carbon bond formation in drug metabolism

  2025cites this paper
• The chemistry of Obermayer test for indican in urine

  2025cites this paper
• A Scalable and Sustainable Synthesis of Indirubin Frameworks Enabled by Deep Eutectic Solvents

  2025cites this paper
• Hairy root culture of Strobilanthes cusia for the production and enhancement of indigo biosynthesis

  2024cites this paper
• Peptide-based metalloporphyrin catalysts: unveiling the role of the metal ion in indole oxidation.

  2023cites this paper
• Indirubin: Nature finding efficient light-activated protective molecular mechanisms

  2023cites this paper
• Following Nature's Footprint: Mimicking the High-Valent Heme-Oxo Mediated Indole Monooxygenation Reaction Landscape of Heme Enzymes.

  2022cites this paper
• Indigo dyeing from Isatis tinctoria L.: From medieval to modern use

  2022cites this paper
• Highly Selective Indole Oxidation Catalyzed by a Mn-Containing Artificial Mini-Enzyme

  2021cites this paper
• Synthesis of Indigo-Dyes from Indole Derivatives by Unspecific Peroxygenases and Their Application for In-Situ Dyeing

  2021cites this paper
• Enzymatically triggered chromogenic cross-linking agents under physiological conditions

  2020cites this paper
• Exploring an anomaly: the synthesis of 7,7′-diazaindirubin through a 7-azaindoxyl intermediate

  2020cites this paper
• Bisindole

  2020cites this paper
• Engineering of an archaeal phosphodiesterase to trigger aggregation-induced emission (AIE) of synthetic substrates

  2020cites this paper
• Elucidating Cysteine-Assisted Synthesis of Indirubin by a Flavin-Containing Monooxygenase

  2019cites this paper
• Characterization of the microbiota in long- and short-term natural indigo fermentation

  2019cites this paper
• Indirubin, a Constituent of the Chinese Herbal Medicine Qing-Dai, Attenuates Dextran Sulfate Sodium-induced Murine Colitis.

  2018cites this paper
• Formation and Cleavage of C-C Bonds by Enzymatic Oxidation-Reduction Reactions.

  2018cites this paper
• Synthesis, Photophysical, Electrochemical, and Halochromic Properties of peri-Naphthoindigo.

  2018cites this paper
• Exploring Novel Anticancer Approaches: Design, Synthesis and Biological Evaluation of Small Molecules and NGR Tumor-Homing Peptides

  2017cites this paper
• Identification of a Water-Soluble Indirubin Derivative as Potent Inhibitor of Insulin-like Growth Factor 1 Receptor through Structural Modification of the Parent Natural Molecule.

  2017cites this paper
• One step synthesis of indirubins by reductive coupling of isatins with KBH4

  2017cites this paper
• Drug Discovery from Mother Nature

  2016cites this paper
• Toward the Development of Specific G-Quadruplex Binders: Synthesis, Biophysical, and Biological Studies of New Hydrazone Derivatives.

  2016cites this paper
• The Role of Indirubins in Inflammation and Associated Tumorigenesis.

  2016cites this paper
• Towards a theory of innovation in handloom weaving in India

  2016cites this paper
• Indirubin derivatives: a patent review (2010 – present)

  2015cites this paper
• Planar and distorted indigo as the core motif in novel chromophoric liquid crystals

  2015cites this paper
• Indigo dye and reduction techniques

  2015cites this paper
• Metabolomics-Driven Discovery of a Prenylated Isatin Antibiotic Produced by Streptomyces Species MBT28.

  2015cites this paper
• Indigo dye production by enzymatic mimicking based on an iron(III)porphyrin

  2014cites this paper
• Biomimetic oxidation of indole by Mn(III)porphyrins

  2014cites this paper
• A colorful history: the evolution of indigoids.

  2014cites this paper
• Progress in the Chemistry of Organic Natural Products 99

  2014cites this paper
• A FACILE ONE-POT SYNTHESIS OF MODEL DIETHYL 6,6'-DIOXOTETRAHYDRO-5,5'-BI(1,2,4-TRIAZINE)-5,5'-DICARBOXYLATES

  2014cites this paper
• A novel indigoid anti-tuberculosis agent.

  2014cites this paper
• 7,7'-Diazaindirubin--a small molecule inhibitor of casein kinase 2 in vitro and in cells.

  2014cites this paper
• Reactivities of indoleamine 2,3-dioxygenases

  2013cites this paper
• Construction of biocatalysts using the myoglobin scaffold for the synthesis of indigo from indole

  2012cites this paper
• From Tyrian Purple to Kinase Modulators: Naturally Halogenated Indirubins and Synthetic Analogues

  2012cites this paper
• Indole peroxygenase activity of indoleamine 2,3-dioxygenase

  2012cites this paper
• Synthesis and Bioactivity of Carbohydrate Derivatives of Indigo, Its Isomers and Heteroanalogues

  2011cites this paper
• Analysis of the extracts of Isatis tinctoria by new analytical approaches of HPLC, MS and NMR.

  2011cites this paper
• Development of a Practical One-Pot Synthesis of Indigo from Indole

  2011cites this paper
• Spin delocalisation in heterocyclic captodative radicals1,2

  2010cites this paper
• Development of a highly efficient indigo dyeing method using indican with an immobilized beta-glucosidase from Aspergillus niger.

  2010cites this paper
• Synthesis and cytotoxicity of novel indirubin-5-carboxamides.

  2010cites this paper
• Voltammetry and spectroelectrochemistry of solid indigo dispersed in carbon paste

  2010cites this paper
• Cytochrome P450 BM-3 Evolved by Random and Saturation Mutagenesis as an Effective Indole-Hydroxylating Catalyst

  2008cites this paper
• The tryptophan aminotransferase Tam1 catalyses the single biosynthetic step for tryptophan‐dependent pigment synthesis in Ustilago maydis

  2008cites this paper
• Formation of the indigo precursor indican in genetically engineered tobacco plants and cell cultures.

  2007cites this paper
• Theoretical study of structure and properties of a molecular reactor based on the urea-linked β-cyclodextrin dimer

  2007cites this paper
• Complex reactions catalyzed by cytochrome P450 enzymes.

  2007cites this paper
• First synthesis of indirubin N-glycosides (red sugars)

  2006cites this paper
• Substitution and chemical environment effects on the absorption spectrum of indigo.

  2006cites this paper
• Analysis of Coumarin 7-Hydroxylation Activity of Cytochrome P450 2A6 using Random Mutagenesis*

  2005cites this paper
• Formation and metabolism of the tryptophan-derived 6-formylindolo[3,2-b]carbazole - a light-induced Ah-receptor ligand

  2005cites this paper
• Identification of indigoid dyes in natural organic pigments used in historical art objects by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry.

  2004cites this paper
• Aryl hydrocarbon receptor response to indigoids in vitro and in vivo.

  2004cites this paper
• Synthesis of heterocycles from anthranilic acid and its derivatives

  2004cites this paper
• Transient induction of cytochromes P450 1A1 and 1B1 in MCF-7 human breast cancer cells by indirubin.

  2003cites this paper
• Oxidative Destruction of Anthraquinone and Indigoid Compounds in Aqueous Solutions of Sodium Hydroxymethylsulfinate

  2003cites this paper
• Hydroxylation of Indole by Laboratory-evolved 2-Hydroxybiphenyl 3-Monooxygenase*

  2002cites this paper
• Sulfation of indoxyl by human and rat aryl (phenol) sulfotransferases to form indoxyl sulfate

  2002cites this paper
• Hepatic microsomal metabolism of indole to indoxyl, a precursor of indoxyl sulfate

  2001cites this paper
• The Thionium/N-Acyliminium Ion Cyclization Cascade as a Strategy for the Synthesis of Azapolycyclic Ring Systems

  2000cites this paper
• WHAT MAKES P450s WORK? SEARCHES FOR ANSWERS WITH KNOWN AND NEW P450s*

  2000cites this paper
• Synthesis of [b]-Anellated Pyrroles via an Acylation Approach

  1999cites this paper
• Formation of indigo by recombinant mammalian cytochrome P450.

  1999cites this paper
• Cyclodextrins as Molecular Templates

  1999cites this paper
• N,N'-Bis(6A-deoxy-β-cyclodextrin-6A-yl)urea as a molecular template in the formation of indigoid dyes

  1998cites this paper
• Bis(benzo[4,5]thieno)[3,2‐c:2′,3′‐e][1,2]dithiin, ein Valenzisomer von „Dithioxo‐thioindigo”︁

  1994cites this paper
• Cyclodehydration of 4-[(Carboxymethyl)amino]pyridin-2-ones. A New, Efficient Synthesis of Pyrrolo[3,2-c]pyridin-4-ones and Pyrido[3,4-b]pyrrolizidin-1-ones

  1994cites this paper
• Novel One-pot Synthesis of Indigo from Indole and Organic Hydroperoxide

  1994cites this paper
• 3-Oxo 3H-indole from dioxygen copper-catalyzed oxidation of indole: One-flask synthesis of 2-dialkylamino 3-oxo 3H-indoles.

  1993cites this paper
• Palladium-Catalyzed Coupling of 3-Indolyl Triflate. Syntheses of 3-Vinyl and 3-Alkynylindoles

  1992cites this paper
• Oxidation of mesoionic oxazolones by oxygen

  1991cites this paper
• Lichtabsorption sowie Kristall- und Molekülstruktur von N,'N'-Dimethylindigo : ein Beispiel für die Anwendung von Synchrotronstrahlung

  1991cites this paper
• Isolation of Four 2,3,5,6,11,11b-Hexahydro-3-oxo-1H-indolizino[8,7-b]indole-5-carboxylic Acids from Clerodendron Trichotomum Thunb and Properties of Their Derivatives

  1989cites this paper
• Oxidative formation of a blue pigment from a dihydropyrrolo[2,1-a]isoquinolin-3(2H)-one derivative.

  1988cites this paper
• Free Radical Chain Processes in Aliphatic Systems involving an Electron Transfer Reaction

  1988cites this paper
• Autoxidation of Indolo[3,2,1-de][1,5]naphthyridines

  1987cites this paper
• Isomers and aza‐analogues of indoxyl containing nitrogen at a ring‐fusion position: Coupling reactions with electrophiles and attempted oxidations

  1986cites this paper
• Investigation of the reactions of fluorinated isatins and N-acetylisatins with thiocarbohydrazide: Synthesis of a novel spiro system: 2-oxo-1′,2′,4′,5′-tetrahydrospiro[3H-indole-3,3′-1,2,4,5-tetrazine]-6′-thione†

  1986cites this paper
• Couplage okydatif facile d'anions substitues captodativement

  1985cites this paper
• The captodative effect

  1985cites this paper
• Radical anions from N,N′‐dimethylisoindigo and its methoxyderivatives

  1982cites this paper
• Kreuzkonjugierte Cyanine und Merocyanine aus Salzen 1‐substituierter 2,3‐Dimethylchinoxaline. 1. Mitteilung. Über die Isolierung der Farbbasen nach spontaner Umwandlung und nach Oxydation der Reaktanten mit Kupfer(II)acetat oder Silberoxid

  1981cites this paper
• Theoretische und spektroskopische Untersuchungen an Indigofarbstoffen, XXI. Synthese und spektroskopische Eigenschaften von 4,4,4′,4′-Tetramethyl[2,2′-bipyrrolidinyliden]-3,3′-dion, einer Verbindung mit dem Grundchromophorsystem des Indigos

  1980cites this paper
• The structure of 2,3,5-trisubstituted 2-pyrrolin-4-ones

  1980cites this paper
• Capto‐dative Substituent Effects in Syntheses with Radicals and Radicophiles [New synthetic methods (32)]

  1979cites this paper
• Decomposition at 90.degree.C of the cholinesterase substrate indoxyl acetate impregnated on paper supports

  1979cites this paper
• High resolution gas chromatographic/real-time high resolution mass spectrometric identification of organic acids in human urine.

  1979cites this paper
• Capto‐dative Substituenteneffekte bei der Synthese mit Radikalen und Radikophilen

  1979cites this paper
• Theoretische und spektroskopische Untersuchungen an Indigofarbstoffen, XIX: Synthese und spektroskopische Eigenschaften eines sechsgliedrigen Thioindigo‐Grundchromophor‐Ringsystems

  1978cites this paper
• Mehrstufige organische Redoxysteme — ein allgemeines Strukturprinzip

  1978cites this paper
• New Indigo Syntheses. Preliminary Communication

  1977cites this paper
• Favorskii rearrangements—I

  1976cites this paper
• Kinetics of the Autoxidation of Substituted Anthranols to Anthraquinones in Buffered Aqueous Dioxane

  1974cites this paper