Catalytic oxidative cyclocondensation of o-aminophenols to 2-amino-3H-phenoxazin-3-ones

Synthetic Communications

Volumn 37, Issue 11, 2007, Pages 1779-1789

  Giurg, Mirosław ^a   Piekielska, Katarzyna ^a   Gȩbala, Magdalena ^a   Ditkowski, Bartosz ^a   Wolański, Marcin ^a   Peczyńska Czoch, Wanda ^a   Młochowski, Jacek ^a  

^a WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

2 aminophenoxazin 3 ones; Enzymes; Hydroperoxides; O aminophenols; Organoselenium compounds; Oxidation

Indexed keywords

2 AMINO 1,4ALPHA DIHYDRO 4ALPHA,8 DIMETHYL 2H PHENOXAZIN 2 ONE; 2 AMINO 1,9 DICARBOXY 4,6 DIMETHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 1,9 DIMETHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 3H PHENOXAZIN 3 ONE DERIVATIVE; 2 AMINO 4,4ALPHA DIHYDRO 4ALPHA,7 DIMETHYL 3H PHENOXAZIN 3 ONE; 2 AMINO 7 CHLORO 3H PHENOXAZIN 3 ONE; 2 AMINO 8 CHLORO 3H PHENOXAZIN 3 ONE; 2 AMINOPHENOL; ACTINOCIN; ANTINEOPLASTIC AGENT; CHLORIDE; CHLORINE; CINNABARINIC ACID; DACTINOMYCIN; EBSELEN; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; LACCASE; METHYL GREEN; OXIDIZING AGENT; QUESTIOMYCIN A; SELENIDE; UNCLASSIFIED DRUG;

AIR; ARTICLE; ATOM; CATALYSIS; DRUG STRUCTURE; MOLECULE; POLYMERIZATION;

EID: 34250307914     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701316136     Document Type: Article

References (36)

1. (a) Estlin, E. L.; Veal, G. J. Clinical and cellular pharmacology in relation to solid tumours of childhood. Cancer Treatment Reviews 2003, 29, 253-273;
2. (b) Hollstein, U. Actinomycin: Chemistry and mechanisms of action. Chem. Rev. 1974, 74, 625-652.
3. Fomsgaard, I. S.; Mortensen, A. G.; Carlsen, S. C. K. Microbial transformation products of benzoxazolinone and benzoxazinone allelochemicals - A review. Chemosphere 2004, 54, 1025-1038.
4. Anzai, K.; Isono, K.; Ohkuma, K.; Suzuki, S. The new antibiotics, Questiomycin A and B. J. Antibiot. (Tokyo), Ser. A 1960, 13, 125-132.
5. (a) Iwata, A.; Yamagucchi, T.; Sato, K.; Izumi, R.; Tomoda, A. Antiviral activity of 2-amino-4,4α-dihydro-4α,7-methyl-3H-phenoxazine- 3-one on poliovirus. Tohoku J. Exp. Med. 2003, 200, 161-165;
6. (b) Schimamoto, T.; Tomoda, A.; Ishida, R.; Ohyashiki, K. Antitumor effects of a novel phenoxazine derivative on human leukemia cell lines in vitro and in vivo. Clin. Cancer Res. 2001, 7, 704-708.
7. Igarashi, Y.; Takagi, K.; Kajiura, T.; Furumai, T.; Oki, T. Glucosylquestiomycin, a novel antibiotic from Microbispora sp. TP-A0184: Fermentation, isolation, structure determination, synthesis and biological activities. J. Antibiot. 1998, 51, 915-920.
8. Shimizu, S.; Suzuki, M.; Tomoda, A.; Arai, S.; Taguchi, H.; Hanawa, T.; Kamiya, S. Phenoxazine compounds produced by the reactions with bovine hemoglobin show antimicrobial activity against non-Tuberculosis mycobacteria. Tohoku Exp. Med. 2004, 203, 47-52.
9. Dorrestein, P.; Begley, T. P. Oxidative cascades: A facile biosynthetic strategy for the assembly of complex molecules. Bioorganic Chemistry 2005, 33, 136-148.
10. Eggert, C. Laccase-catalyzed formation of cinnabarinic acid is responsible for antibacterial activity of Pycnoporus cinnabarinus. Microbiol. Res. 1997, 152, 315-318.
11. Hughes, M. A.; Baggs, M. J.; al-Dulayymi, J.; Baird, M. S.; Williams, P. A. 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. 2002, 68, 4965-4970.
12. (a) Nagasawa, H. T.; Gutmann, H. R.; Morgan, M. A. The oxidation of o-aminophenols by cytochrome c and cytochrome oxidase, II: Synthesis and identification of oxidation products. J. Biol. Chem. 1959, 234, 1600-1604;
13. (b) Cavill, G. W. K.; Clezy, P. S.; Whitfield, F. B. The chemistry of mould metabolites - IV: Reductive acetylation and reoxidation of some phenoxazin-3-one. Tetrahedron 1961, 12, 139-145;
14. (c) Nogami, T.; Hishida, T.; Yamada, M.; Mikawa, H.; Shirota, Y. Formation and reactions of o-benzoquinone mono- and di- imines. Bull. Chem. Soc. Jpn. 1975, 48, 3709-3714.
15. Kaizer, J.; Csonka, R.; Speier, G. TEMPO-initiated oxidation of 2-aminophenol to 2-aminophenoxazin-3-one. J. Mol. Catal. A: Chem. 2002, 180, 91-96.
16. Maruyama, K.; Moriguchi, T.; Mashino, T.; Nishinaga, A. Highly selective formation of 2-aminophenoxazin-3-one by catalytic oxygenation of o-aminophenol. Chem. Lett. 1996, 819-820.
17. (a) Maurya, M. R.; Sikarwar, S.; Joseph, T.; Halligudi, S. B. 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. 2005, 236, 132-138;
18. (b) Marinescu, L.; Mølbach, M.; Rousseau, C.; Bols, M. Supramolecular oxidation of anilines using hydrogen peroxide as stoichiometric oxidant. J. Am. Chem. Soc. 2005, 127, 17578-17579;
19. (c) Horvath, T.; Kaizer, J.; Speier, G. Functional phenoxazinone synthase models: Kinetic studies on the copper catalyzed oxygenation of 2-aminophenol. J. Mol. Catal. A: Chem. 2004, 215, 9-15;
20. (d) Simandi, L. I.; Simandi, T. M.; May, Z.; Besenyei, G. Catalytic activation of dioxygen by oximatocobalt(II) and oximatoiron (II) complexes for catecholase-mimic oxidations of o-substituted phenols. Coord. Chem. Rev. 2003, 245, 85-93.
21. Giurg, M.; Wiech, E.; Piekielska, K.; Gȩbala, M.; Młochowski, J.; Wolański, M.; Ditkowski, B.; Peczyńska- Czoch, W. A new approach to synthesis of questiomycin A: Oxidative cyclocondensation of ortho-aminophenol. Polish J. Chem. 2006, 80, 297-306.
22. (a) Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B. Large-scale oxidations in the pharmaceutical industry. Chem. Rev. 2006, 106, 2943-2989;
23. (b) Franz, G.; Scheldon, R. A. Ullman's Encyclopedia of Industrial Chemistry, 6th ed.; Wiley-VCH, Weinheim, 2003; Vol. 24, pp. 487-544.
24. (a) Wójtowicz, H.; Młochowski, J.; Syper, L.; Yadav, H. S. t-Butyl hydroperoxide oxidative dealkylation of hydroquinone ethers to 1,4-quinones. Synth. Commun. 2006, 36, 1991-2000;
25. (b) Giurg, M.; Brza̧szcz, M.; Młochowski, J. Hydroperoxide oxidation of different organic compounds catalyzed by silica-supported selenenamide. Polish J. Chem. 2006, 80, 417-428;
26. (c) Młochowski, J.; Brza̧szcz, M.; Chojnacka, M.; Giurg, M.; Wójtowicz, H. Diaryldiselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents. Arkivoc 2004, 3, 226-248;
27. (d) Młochowski, J.; Brza̧szcz, M.; Giurg, M.; Palus, J.; Wójtowicz, H. Selenium-promoted oxidation of organic compounds: Reactions and mechanisms. Eur. J. Org. Chem. 2003, 4329-4339.
28. (a) Riva, S. Laccases: Blue enzymes for green chemistry. Trends Biotechnol. 2006, 24, 219-226;
29. (b) Frey, P. A.; Hegeman, A. D.; Reed, G. H. Free radical mechanisms in enzymology. Chem. Rev. 2006, 106, 3302-3316.
30. (a) Osiadacz, J.; Aladhami, A. J. H.; Bajraszewska, D.; Fischer, P.; Peczyńska-Czoch, W. On the use of Trametes versicolor laccase for conversion of 4-methyl-3-hydroxyanthranilic acid to actinocin chromophore. J. Biotechnol. 1999, 72, 141-149;
31. (b) Młochowski, J.; Kloc, K.; Syper, L.; Ingot, D. A.; Piasecki, E. Aromatic and azaaromatic diselenides, benzisoselenazolones and related compounds as immunomodulators active in humans: Synthesis and properties. Liebigs Ann. Chem. 1993, 1239-1244.
32. Bolognese, A.; Correale, G.; Manfra, M.; Lavecchia, A.; Novellino, E.; Pele, S. Antitumor agents, 5: Synthesis, structure-activity relationships, and biological evaluation of dimethyl-5H-pyridophenoxazin-5-ones, and tetrahydro-5H-benzopyridophenoxazin-5-ones and 5H-benzo-pyridophe with potent antiproliferative activity. J. Med. Chem. 2006, 495, 5110-5118.
33. Chu, W.; Kamitori, S.; Shinomiya, M.; Carlson, R. G.; Takusagawa, F. Toward the design of an RNA:DNA hybrid binding agent. J. Am. Chem. Soc. 1994, 116, 2243-2253.
34. Musso, H. Phenoxazine. VII: Bildungsweisen für 4,5- dimethylphenoxazon-3-isocyanat. Chem. Ber. 1963, 96, 1945-1967.
35. 1U = 1.0 mmol of syringaldazine oxidized to quinone per 60 s at 25°C. Leonowicz, A.; Grzywnowicz, K. Oxidative estimation of laccase forma in some whiterot fungi using syringaldazine as substrate. Enzyme Microb. Techno. 1981, 3, 55-58.
36. 1U = 1.0 mg of purpurogallin formed from pyrogallol in 20 s at pH 6.0 at 20°C. Hewson, W. D.; Hager, L. P. The Porphyrins; Dolphin, D. (Ed.) Academic: New York 1979; Vol. 7, pp. 295-332.