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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

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Pages 1779-1789 | Received 05 Oct 2006, Published online: 30 Jun 2007

References

  • Estlin , E. L. and Veal , G. J. 2003 . Clinical and cellular pharmacology in relation to solid tumours of childhood . Cancer Treatment Reviews , 29 : 253 – 273 .
  • Hollstein , U. 1974 . Actinomycin: Chemistry and mechanisms of action . Chem. Rev. , 74 : 625 – 652 .
  • Fomsgaard , I. S. , Mortensen , A. G. and Carlsen , S. C. K. 2004 . Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals—A review . Chemosphere , 54 : 1025 – 1038 .
  • Anzai , K. , Isono , K. , Ohkuma , K. and Suzuki , S. 1960 . The new antibiotics, Questiomycin A and B . J. Antibiot. (Tokyo), Ser. A , 13 : 125 – 132 .
  • Iwata , A. , Yamagucchi , T. , Sato , K. , Izumi , R. and Tomoda , A. 2003 . Antiviral activity of 2‐amino‐4,4α‐dihydro‐4α,7‐methyl‐3H‐phenoxazine‐3‐one on poliovirus . Tohoku J. Exp. Med. , 200 : 161 – 165 .
  • Schimamoto , T. , Tomoda , A. , Ishida , R. and Ohyashiki , K. 2001 . Antitumor effects of a novel phenoxazine derivative on human leukemia cell lines in vitro and in vivo . Clin. Cancer Res. , 7 : 704 – 708 .
  • Igarashi , Y. , Takagi , K. , Kajiura , T. , Furumai , T. and Oki , T. 1998 . Glucosylquestiomycin, a novel antibiotic from Microbispora sp. TP‐A0184: Fermentation, isolation, structure determination, synthesis and biological activities . J. Antibiot. , 51 : 915 – 920 .
  • Shimizu , S. , Suzuki , M. , Tomoda , A. , Arai , S. , Taguchi , H. , Hanawa , T. and Kamiya , S. 2004 . Phenoxazine compounds produced by the reactions with bovine hemoglobin show antimicrobial activity against non‐Tuberculosis mycobacteria . Tohoku Exp. Med. , 203 : 47 – 52 .
  • Dorrestein , P. and Begley , T. P. 2005 . Oxidative cascades: A facile biosynthetic strategy for the assembly of complex molecules . Bioorganic Chemistry , 33 : 136 – 148 .
  • Eggert , C. 1997 . Laccase‐catalyzed formation of cinnabarinic acid is responsible for antibacterial activity of Pycnoporus cinnabarinus . Microbiol. Res. , 152 : 315 – 318 .
  • Hughes , M. A. , Baggs , M. J. , al‐Dulayymi , J. , Baird , M. S. and Williams , P. A. 2002 . Accumulation of 2‐aminophenoxazin‐3‐one‐7‐carboxylate during growth of Pseudomonas putida TW3 on 4‐nitrosubstituted substrates requires 4-hydroxylaminobenzoate lyase (PnbB) . Appl. Environ. Microbiol. , 68 : 4965 – 4970 .
  • Nagasawa , H. T. , Gutmann , H. R. and Morgan , M. A. 1959 . The oxidation of o‐aminophenols by cytochrome c and cytochrome oxidase, II: Synthesis and identification of oxidation products . J. Biol. Chem. , 234 : 1600 – 1604 .
  • Cavill , G. W. K. , Clezy , P. S. and Whitfield , F. B. 1961 . The chemistry of mould metabolites—IV: Reductive acetylation and reoxidation of some phenoxazin‐3‐one . Tetrahedron , 12 : 139 – 145 .
  • Nogami , T. , Hishida , T. , Yamada , M. , Mikawa , H. and Shirota , Y. 1975 . Formation and reactions of o‐benzoquinone mono‐ and di‐ imines . Bull. Chem. Soc. Jpn. , 48 : 3709 – 3714 .
  • Kaizer , J. , Csonka , R. and Speier , G. 2002 . TEMPO‐initiated oxidation of 2-aminophenol to 2-aminophenoxazin-3-one . J. Mol. Catal. A: Chem. , 180 : 91 – 96 .
  • Maruyama , K. , Moriguchi , T. , Mashino , T. and Nishinaga , A. 1996 . Highly selective formation of 2‐aminophenoxazin‐3‐one by catalytic oxygenation of o‐aminophenol . Chem. Lett. , : 819 – 820 .
  • Maurya , M. R. , Sikarwar , S. , Joseph , T. and Halligudi , S. B. 2005 . Bis(2‐[α‐hydroxyethyl]benzimidazolato)copper(II) anchored onto chloromethylated polystyrene for the biomimetic oxidative coupling of 2‐aminophenol to 2‐aminophenoxazine‐3‐one . J. Mol. Catal. A: Chem. , 236 : 132 – 138 .
  • Marinescu , L. , Mølbach , M. , Rousseau , C. and Bols , M. 2005 . Supramolecular oxidation of anilines using hydrogen peroxide as stoichiometric oxidant . J. Am. Chem. Soc. , 127 : 17578 – 17579 .
  • Horvath , T. , Kaizer , J. and Speier , G. 2004 . Functional phenoxazinone synthase models: Kinetic studies on the copper catalyzed oxygenation of 2‐aminophenol . J. Mol. Catal. A: Chem. , 215 : 9 – 15 .
  • Simandi , L. I. , Simandi , T. M. , May , Z. and Besenyei , G. 2003 . Catalytic activation of dioxygen by oximatocobalt(II) and oximatoiron (II) complexes for catecholase-mimic oxidations of o-substituted phenols . Coord. Chem. Rev. , 245 : 85 – 93 .
  • Giurg , M. , Wiech , E. , Piekielska , K. , Gębala , M. , Młochowski , J. , Wolański , M. , Ditkowski , B. and Peczyńska-Czoch , W. 2006 . A new approach to synthesis of questiomycin A: Oxidative cyclocondensation of ortho‐aminophenol . Polish J. Chem. , 80 : 297 – 306 .
  • Caron , S. , Dugger , R. W. , Ruggeri , S. G. , Ragan , J. A. and Ripin , D. H. B. 2006 . Large‐scale oxidations in the pharmaceutical industry . Chem. Rev. , 106 : 2943 – 2989 .
  • Franz , G. and Scheldon , R. A. 2003 . Ullman's Encyclopedia of Industrial Chemistry , 6th ed. Vol. 24 , 487 – 544 . Weinheim : Wiley‐VCH .
  • Wójtowicz , H. , Młochowski , J. , Syper , L. and Yadav , H. S. 2006 . t‐Butyl hydroperoxide oxidative dealkylation of hydroquinone ethers to 1,4‐quinones . Synth. Commun. , 36 : 1991 – 2000 .
  • Giurg , M. , Brza¸szcz , M. and Młochowski , J. 2006 . Hydroperoxide oxidation of different organic compounds catalyzed by silica‐supported selenenamide . Polish J. Chem. , 80 : 417 – 428 .
  • Młochowski , J. , Brza¸szcz , M. , Chojnacka , M. , Giurg , M. and Wójtowicz , H. 2004 . Diaryldiselenides and benzisoselenazol‐3(2H)-ones as oxygen‐transfer agents . Arkivoc , 3 : 226 – 248 .
  • Młochowski , J. , Brza¸szcz , M. , Giurg , M. , Palus , J. and Wójtowicz , H. 2003 . Selenium‐promoted oxidation of organic compounds: Reactions and mechanisms . Eur. J. Org. Chem. , : 4329 – 4339 .
  • Riva , S. 2006 . Laccases: Blue enzymes for green chemistry . Trends Biotechnol. , 24 : 219 – 226 .
  • Frey , P. A. , Hegeman , A. D. and Reed , G. H. 2006 . Free radical mechanisms in enzymology . Chem. Rev. , 106 : 3302 – 3316 .
  • Osiadacz , J. , Aladhami , A. J. H. , Bajraszewska , D. , Fischer , P. and Peczyńska‐Czoch , W. 1999 . On the use of Trametes versicolor laccase for conversion of 4‐methyl‐3‐hydroxyanthranilic acid to actinocin chromophore . J. Biotechnol. , 72 : 141 – 149 .
  • Młochowski , J. , Kloc , K. , Syper , L. , Ingot , D. A. and Piasecki , E. 1993 . Aromatic and azaaromatic diselenides, benzisoselenazolones and related compounds as immunomodulators active in humans: Synthesis and properties . Liebigs Ann. Chem. , : 1239 – 1244 .
  • Bolognese , A. , Correale , G. , Manfra , M. , Lavecchia , A. , Novellino , E. and Pele , S. 2006 . Antitumor agents, 5: Synthesis, structure–activity relationships, and biological evaluation of dimethyl‐5H‐pyridophenoxazin‐5‐ones, and tetrahydro-5H‐benzo-pyridophenoxazin‐5‐ones and 5H-benzo-pyridophe with potent antiproliferative activity . J. Med. Chem. , 495 : 5110 – 5118 .
  • Chu , W. , Kamitori , S. , Shinomiya , M. , Carlson , R. G. and Takusagawa , F. 1994 . Toward the design of an RNA:DNA hybrid binding agent . J. Am. Chem. Soc. , 116 : 2243 – 2253 .
  • Musso , H. Phenoxazine . 1963 . VII: Bildungsweisen für 4,5‐dimethylphenoxazon‐3‐isocyanat . Chem. Ber. , 96 : 1945 – 1967 .
  • Leonowicz , A. and Grzywnowicz , K. 1981 . Oxidative estimation of laccase forma in some whiterot fungi using syringaldazine as substrate . Enzyme Microb. Techno. , 3 : 55 – 58 . 1U=1.0 µmol of syringaldazine oxidized to quinone per 60 s at 25°C
  • Hewson , W. D. and Hager , L. P. 1979 . The Porphyrins Edited by: Dolphin , D. Vol. 7 , 295 – 332 . New York : Academic . 1U=1.0 mg of purpurogallin formed from pyrogallol in 20 s at pH 6.0 at 20°C

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