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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 11
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Original Articles

Catalytic Oxidative Cyclocondensation of o‐Aminophenols to 2‐Amino‐3H‐phenoxazin‐3‐ones

Mirosław Giurg Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, PolandCorrespondence[email protected]
,
Katarzyna Piekielska Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, Poland
,
Magdalena Gębala Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, Poland
,
Bartosz Ditkowski Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, Poland
,
Marcin Wolański Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, Poland
,
Wanda Peczyńska‐Czoch Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, Poland
&
Jacek Młochowski Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, Wrocław, Poland
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Pages 1779-1789 | Received 05 Oct 2006, Published online: 30 Jun 2007

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K. Helios, H. Maniak, M. Sowa, W. Zierkiewicz, M. Wąsińska-Kałwa, M. Giurg, P. Drożdżewski, A. Trusek-Hołownia, M. Malik & K. Krauze. (2017) Silver(I) complex with 2-amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazin-3-one (Phx-1) ligand: crystal structure, vibrational spectra and biological studies. Journal of Coordination Chemistry 70:20, pages 3471-3487.
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Mirosław Giurg & Ludwik Syper. (2008) Diaryl Diselenides and Related Compounds as Oxygen-Transfer Agents. Phosphorus, Sulfur, and Silicon and the Related Elements 183:4, pages 970-985.
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Articles from other publishers (43)

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M. A. Giricheva, A. V. Pokrovskaya, D. A. Davydov & A. V. Budruev. (2023) Synthesis of 2-aminophenoxazin-3-ones by photolysis of 2-azidophenol and 2-aminophenols. Russian Chemical Bulletin 72:9, pages 2133-2137.
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Poosa Mallesham, Venkatesh Miriyala, Satyanarayana Yennam, Paul Douglas Sanasi & Manoranjan Behera. (2023) Propylphosphonic Anhydride (T3P®)‐ Mediated Efficient Synthesis of Substituted 2‐Amino Phenoxazinones. ChemistrySelect 8:26.
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Veronika Hahn. (2023) Potential of the enzyme laccase for the synthesis and derivatization of antimicrobial compounds. World Journal of Microbiology and Biotechnology 39:4.
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Thomas G. Back. 2023. Chalcogen Chemistry: Fundamentals and Applications. Chalcogen Chemistry: Fundamentals and Applications 334 383 .
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Annett Mikolasch & Veronika Hahn. (2021) Laccase-Catalyzed Derivatization of Antibiotics with Sulfonamide or Sulfone Structures. Microorganisms 9:11, pages 2199.
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Ana Catarina Sousa, Lígia O. Martins & M. Paula Robalo. (2021) Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores. Molecules 26:12, pages 3719.
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Ashish Kumar Dhara, Sayantan Maity & Basab Bijayi Dhar. (2021) Visible-Light-Mediated Synthesis of Substituted Phenazine and Phenoxazinone Using Eosin Y as a Photoredox Catalyst. Organic Letters 23:9, pages 3269-3273.
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Fei Peng, Bingjie Zheng, Yao Zhang, Aroosha Faheem, Yanyan Chai, Tao Jiang, Xuguang Chen & Yonggang Hu. (2020) Biocatalytic Oxidation of Aromatic Compounds by Spore-Based System. ACS Sustainable Chemistry & Engineering 8:37, pages 14159-14165.
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Narayan Ch. Jana, Paula Brandão & Anangamohan Panja. (2020) The first report of a tetra-azide bound mononuclear cobalt( iii ) complex and its comparative biomimetic catalytic activity with tri-azide bound cobalt( iii ) compounds . New Journal of Chemistry 44:27, pages 11527-11536.
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Nataliya Voloshchuk, Vadim Schütz, Laura Laschke, Andrii P. Gryganskyi & Margot Schulz. (2020) The Trichoderma viride F-00612 consortium tolerates 2-amino-3H-phenoxazin-3-one and degrades nitrated benzo[d]oxazol-2(3H)-one. Chemoecology 30:2, pages 79-88.
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Laura Gasque, Alan Mendieta & Gerardo Ferrer-Sueta. (2020) Comment on “Mixed azido/phenoxido bridged trinuclear Cu( ii ) complexes of Mannich bases: synthesis, structures, magnetic properties and catalytic oxidase activities”, Dalton Trans. , 2018, 47 , 9385–9399 and “Tri- and hexa-nuclear Ni II –Mn II complexes of a N 2 O 2 donor unsymmetrical ligand: synthesis, structures, magnetic properties and catalytic oxidase activities”, Dalton Trans. , 2018, 47 , 13957–13971 . Dalton Transactions 49:10, pages 3365-3368.
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Jonas Kühlborn, Matthias Konhäuser, Jonathan Groß, Peter R. Wich & Till Opatz. (2019) Xylochemical Synthesis of Cytotoxic 2-Aminophenoxazinone-Type Natural Products Through Oxidative Cross Coupling. ACS Sustainable Chemistry & Engineering 7:4, pages 4414-4419.
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Ewelina Węglarz-Tomczak, Michał Talma, Mirosław Giurg, Hans V. Westerhoff, Robert Janowski & Artur Mucha. (2018) Neutral metalloaminopeptidases APN and MetAP2 as newly discovered anticancer molecular targets of actinomycin D and its simple analogs. Oncotarget 9:50, pages 29365-29378.
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Ana Catarina Sousa, M. Conceição Oliveira, Lígia O. Martins & M. Paula Robalo. (2017) A Sustainable Synthesis of Asymmetric Phenazines and Phenoxazinones Mediated by CotA‐Laccase. Advanced Synthesis & Catalysis 360:3, pages 575-583.
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Christopher I. Olivares, Camila L. Madeira, Reyes Sierra-Alvarez, Warren Kadoya, Leif Abrell, Jon Chorover & Jim A. Field. (2017) Environmental Fate of 14 C Radiolabeled 2,4-Dinitroanisole in Soil Microcosms . Environmental Science & Technology 51:22, pages 13327-13334.
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Pavel Arsenyan & Jelena Vasiljeva. (2017) Selenazolium salts as catalysts in oxidation reactions. Mendeleev Communications 27:6, pages 621-622.
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Odissa Abou Mehrez, Florence Dossier-Berne & Bernard Legube. (2016) Oxidation of 2-aminophenol to 2-amino-3H-phenoxazin-3-one with monochloramine in aqueous environment: A new method for APO synthesis?. Chemosphere 145, pages 464-469.
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Shaik Mustafa, K. Santhosh Reddy & M.S. Surendra Babu. (2015) Unexpected one pot C (aryl)–N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives. Tetrahedron Letters 56:44, pages 6104-6107.
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Jacek Młochowski & Halina Wójtowicz-Młochowska. (2015) Developments in Synthetic Application of Selenium(IV) Oxide and Organoselenium Compounds as Oxygen Donors and Oxygen-Transfer Agents. Molecules 20:6, pages 10205-10243.
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Suzanne M. Jansze, Vittorio Saggiomo, Antonius T.M. Marcelis, Martin Lutz & Aldrik H. Velders. (2015) 2-Amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazin-3-one as an unexpected product from reduction of 5-methyl-2-nitrophenol. Tetrahedron Letters 56:9, pages 1060-1062.
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Kuldeep Mahiya, Ravinder Kumar, Francisco Lloret & Pavan Mathur. (2014) Oxidation of substituted phenols using copper(II) metallatriangles formed through ligand sharing. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 133, pages 663-668.
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Ana Catarina Sousa, M. Conceição Oliveira, Lígia O. Martins & M. Paula Robalo. (2014) Towards the rational biosynthesis of substituted phenazines and phenoxazinones by laccases. Green Chem. 16:9, pages 4127-4136.
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Salman Y. Jabri & Larry E. Overman. (2013) Enantioselective Total Syntheses of Plectosphaeroic Acids B and C. The Journal of Organic Chemistry 78:17, pages 8766-8788.
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Raffaele PasceriDavid Siegel, David Ross & Christopher J. Moody. (2013) Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A. Journal of Medicinal Chemistry 56:8, pages 3310-3317.
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Salman Y. Jabri & Larry E. Overman. (2013) Enantioselective Total Synthesis of Plectosphaeroic Acid B. Journal of the American Chemical Society 135:11, pages 4231-4234.
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Wendy Zhong, Jiong Yang, Bruce D. Hilton, Wenqing Feng, Gary E. Martin, Jianguo Yin, Kiran Muppalla, Weidong Tong & Xiaoyong Fu. (2013) Structural Characterization of a Benzoxazinophenoxazine Formed as a By‐Product During the Synthesis of a 3‐Amino‐ N , N ‐dimethylsalicylamide . Journal of Heterocyclic Chemistry 50:2, pages 435-437.
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Daniela Gamenara, Gustavo A. Seoane, Patricia Saenz‐Méndez & Pablo Domínguez de María. 2012. Redox Biocatalysis. Redox Biocatalysis 303 432 .
Wendy Zhong, Jiong Yang, Bruce D. Hilton, Gary E. Martin, Jianguo Yin, Kiran Muppalla, Weidong Tong & Xiaoyong Fu. (2012) Structural Characterization of a Phenoxazine Analog Formed as a By‐product of the Synthesis of a 3‐Amino‐ N,N ‐dimethylsalicylamide . Journal of Heterocyclic Chemistry 49:5, pages 1163-1168.
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Gauri Ahuja & Pavan Mathur. (2012) Bis-benzimidazolyl diamide copper (II) complexes: Synthesis, crystal structure and oxidation of substituted amino phenols. Inorganic Chemistry Communications 17, pages 42-48.
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Keshar Prasain, Thi D.T. Nguyen, Maureen J. Gorman, Lydia M. Barrigan, Zeyu Peng, Michael R. Kanost, Lateef U. Syed, Jun Li, Kun Yan Zhu & Duy H. Hua. (2012) Redox potentials, laccase oxidation, and antilarval activities of substituted phenols. Bioorganic & Medicinal Chemistry 20:5, pages 1679-1689.
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Szilvia Hajdok, Jürgen Conrad & Uwe Beifuss. (2011) Laccase-Catalyzed Domino Reactions between Hydroquinones and Cyclic 1,3-Dicarbonyls for the Regioselective Synthesis of Substituted p -Benzoquinones . The Journal of Organic Chemistry 77:1, pages 445-459.
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Daniela Monti, Gianluca Ottolina, Giacomo Carrea & Sergio Riva. (2011) Redox Reactions Catalyzed by Isolated Enzymes. Chemical Reviews 111:7, pages 4111-4140.
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Zvi RappoportJacek Młochowski, Rafał Lisiak & Halina Wójtowicz‐Młochowska. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Yanchun Zhao, Xiulin Yang, Jianniao Tian, Fengyang Wang & Lu Zhan. (2010) Highly dispersed Pd nanoparticles on 2-aminophenoxazin-3-one functionalized MWCNTs surface for methanol electro-oxidation in alkaline media. Materials Science and Engineering: B 171:1-3, pages 109-115.
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Komala Pandurangan, Shane Gallagher, Grace G. Morgan, Helge Müller-Bunz & Francesca Paradisi. (2010) Structure and antibacterial activity of the silver(i) complex of 2-aminophenoxazine-3-one. Metallomics 2:8, pages 530.
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Yanchun Zhao, Xiulin Yang & Jianniao Tian. (2009) Electrocatalytic oxidation of methanol at 2-aminophenoxazin-3-one-functionalized multiwalled carbon nanotubes supported PtRu nanoparticles. Electrochimica Acta 54:27, pages 7114-7120.
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Gavin Carr, Wendy Tay, Helen Bottriell, Sarah K. Andersen, A. Grant Mauk & Raymond J. Andersen. (2009) Plectosphaeroic Acids A, B, and C, Indoleamine 2,3-Dioxygenase Inhibitors Produced in Culture by a Marine Isolate of the Fungus Plectosphaerella cucumerina . Organic Letters 11:14, pages 2996-2999.
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Suteera Witayakran & Arthur J. Ragauskas. (2009) Synthetic Applications of Laccase in Green Chemistry. Advanced Synthesis & Catalysis 351:9, pages 1187-1209.
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Miroslaw Giurg, Katarzyna Piekielska, Magdalena Gebala, Bartosz Ditkowski, Marcin Wolanski, Wanda Peczynska‐Czoch & Jacek Mlochowski. (2007) Catalytic Oxidative Cyclocondensation of o‐Aminophenols to 2‐Amino‐3H‐phenoxazin‐3‐ones.. ChemInform 38:45.
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