Synthesis of 7- and 8-Functionalized 2-Aminophenoxazinones via Cyclocondensation of 2-Aminophenols

Abstract

An efficient protocol for the synthesis of 7- and 8-functionalized 4- and 2-amino-3H-phenoxazin-3-ones and 2-amino-1H-phenoxazin-1-ones by oxidation of 2-aminophenols using hydrogen peroxide activated by ebselen is presented. We demonstrate that formation of the 2-amino-3H-phenoxazin-3-one core requires that the substituents present on one of the reacting substrate molecules be eliminated under oxidative reaction conditions.

Key words

catalysis - ebselen - heterocycles - peroxides - 2-aminophenols

• References

• 1 New address: Jarosław M. Granda, Institute of Organic Chemistry, Polish Academy of Science, Kasprzaka 44/52, 01-224 Warsaw, Poland.
• 2 New address: Katarzyna Piekielska-Kulp, Analytische Chemie – Elektroanalytik & Sensorik, Ruhr-Universität Bochum, Universitätsstraße 150, D-44780 Bochum, Germany.
• 3a Graf E, Schneider K, Nicholson G, Stroebele M, Jones AL, Goodfellow M, Beil W, Suessmuth RD, Fiedler H.-P. J. Antibiot. 2007; 60: 277
• 3b Gomes PB, Nett M, Dahse H.-M, Hertweck C. J. Nat. Prod. 2010; 73: 1461
• 3c Gomes PB, Nett M, Dahse H.-M, Sattler I, Martin K, Hertweck C. Eur. J. Org. Chem. 2010; 231
• 3d Ren J, Liu D, Tian L, Wei Y, Proksch P, Zeng J, Lin W. Bioorg. Med. Chem. Lett. 2013; 23: 301
• 3e Barnes EC, Bezerra-Gomes P, Nett M, Hertweck C. J. Antibiot. 2015; in press: doi: 10.1038/ja.2015.10
• 4a Shimizu S, Suzuki M, Tomoda A, Arai S, Toguchi H, Hanawa T, Kamiya S. Tohoku J. Exp. Med. 2004; 203: 47
• 4b For an excellent review, see: Belz RG. Pest. Manag. Sci. 2007; 63: 308
• 4c Hayashi K, Hayashi T, Miyazawa K, Tomoda A. J. Pharmacol. Sci. 2010; 114: 85
• 4d Bruyneel F, Basosi R, Bols C.-M, Enaud E, Hercher C, Jager JI, Jarosz-Wilkolazka A, Marchand-Brynaert J, Pogni R, Polak J, Vanhulle S. US 2010/0000032 A1, 2010 ; Chem. Abstr. 2010, 152, 121883.
• 5 Pasceri R, Siegel D, Ross D, Moody CJ. J. Med. Chem. 2013; 56: 3310
• 6 Carr G, Tay W, Bottriell H, Andersen SK, Mauk AG, Andersen RJ. Org. Lett. 2009; 11: 2996
• 7 Jabri SY, Overman LE. J. Org. Chem. 2013; 78: 8766
• 8 For a review, see: Hollstein U. Chem. Rev. 1974; 74: 625
• 9 Gebala M, Stoica L, Neugebauer S, Schuhmann W. Electroanalysis 2009; 21: 325
• 10 Yue S, Liu J, Bradford J. WO2010062536, 2010 ; Chem. Abstr. 2010, 153, 11996.
• 11 Jose J, Burgess K. Tetrahedron 2006; 62: 11021
• 12a Diepolder E. Chem. Ber. 1896; 29: 1756
• 12b Kuhn R, Hammer O. Chem. Ber. 1950; 83: 413
• 13 Keum S.-R, Gregory DH, Bruice TC. J. Am. Chem. Soc. 1990; 112: 2711 ; and ref. 6 cited therein
• 14 Ruan JW, Huang ZS, Huang JF, Du CJ, Huang SL, Shi Z, Fu LW, Gu LQ. Chin. Chem. Lett. 2006; 17: 1141
• 15 Korczynski A, Obarski S. Bull. Soc. Chim. Fr. 1923; 33: 1823
• 16 Jabri SY, Overman LE. J. Am. Chem. Soc. 2013; 135: 4231
• 17 Giurg M, Piekielska K, Gębala M, Ditkowski B, Wolański M, Peczyńska-Czoch W, Młochowski J. Synth. Commun. 2007; 37: 1779
• 18a Forte S, Polak J, Valensin D, Taddei M, Basosi R, Vanhulle S, Jarosz-Wilkolazka A, Pogni R. J. Mol. Catal. B: Enzym. 2010; 63: 116
• 18b Sousa AC, Oliveira MC, Martins LO, Robalo MP. Green Chem. 2014; 16: 4127
• 19 Maruyama K, Moriguchi T, Mashino T, Nishinaga A. Chem. Lett. 1996; 819
• 20a Ahuja G, Mathur P. Inorg. Chem. Commun. 2012; 17: 42
• 20b Mahiya K, Kumar R, Lloret F, Mathur P. Spectrochim. Acta, Part A 2014; 133: 663
• 20c Jawale DV, Gravel E, Geertsen V, Li H, Shah N, Namboothiri IN. N, Doris E. ChemCatChem 2014; 6: 719
• 21 Zhong W, Yang J, Hilton BD, Martin GE, Yin J, Muppalla K, Tong W, Fu X. J. Heterocycl. Chem. 2012; 49: 1163

For reviews, see:
• 22a Młochowski J, Brząszcz M, Giurg M, Palus J, Wójtowicz H. Eur. J. Org. Chem. 2003; 4329
• 22b Młochowski J. Phosphorus, Sulfur, Silicon Relat. Elem. 2008; 183: 931
• 22c Freudendahl DM, Santoro S, Shahzad SA, Santi C, Wirth T. Angew. Chem. Int. Ed. 2009; 48: 8409
• 22d Młochowski J, Peczyńska-Czoch W, Piętka-Ottlik M, Wójtowicz-Młochowska H. Open Catal. J. 2011; 4: 54
• 22e Santoro S, Azeredo JB, Nascimento V, Sancineto L, Braga AL, Santi C. RSC Adv. 2014; 4: 31521

For selected recent articles, see:
• 23a Garcia-Marin H, van der Toorn JC, Mayoral JA, Garcia JI, Arends IW. C. E. J. Mol. Catal. A: Chem. 2011; 334: 83
• 23b de Torres M, Arends IW. C. E, Mayoral JA, Pires E, Jimenez-Oses G. Appl. Catal. A 2012; 425–426: 91
• 23c Cheng XY, Li KF, Wang QJ, Wang CY, Ying TK. Chin. Chem. Lett. 2012; 23: 801
• 23d Alberto EE, Braga AL, Detty MR. Tetrahedron 2012; 68: 10476
• 23e Nascimento V, Alberto EE, Tondo DW, Dambrowski D, Detty MR, Nome F, Braga AL. J. Am. Chem. Soc. 2012; 134: 138
• 23f Mercier EA, Smith CD, Parvez M, Back TG. J. Org. Chem. 2012; 77: 3508
• 23g Buckley BR, Elliott CE, Chan Y, Dreyfus N, Bulman Page PC. Synlett 2013; 24: 2266
• 23h Yu L, Wang J, Chen T, Wang Y, Xu Q. Appl. Organomet. Chem. 2014; 28: 652
• 23i Yu L, Wu Y, Cao H, Zhang X, Shi X, Luan J, Chen T, Pan Y, Xu Q. Green Chem. 2014; 16: 287
• 23j Yu L, Li HY, Zhang X, Ye JQ, Liu JP, Xu Q, Lautens M. Org. Lett. 2014; 16: 1346
• 23k Zhao D, Johansson M, Backvall J.-E. Eur. J. Org. Chem. 2007; 4431
• 24 Giurg M, Wiech E, Piekielska K, Gębala M, Młochowski J, Wolański M, Ditkowski B, Peczyńska-Czoch W. Polish J. Chem. 2006; 80: 297
• 25 Barton DH. R, Finet J.-P, Thomas M. Tetrahedron 1988; 44: 6397
• 26a Wójtowicz H, Brząszcz M, Kloc K, Młochowski J. Tetrahedron 2002; 57: 9743
• 26b Młochowski J, Lisiak R, Wójtowicz-Młochowska H In Patai’s Chemistry of Functional Groups, The Chemistry of Organic Selenium and Tellurium Compounds . Part 2, Vol. 3; Patai S, Rappoport Z. Wiley; Chichester: 2012: 1083
• 27 Sarma BK, Mugesh G. Chem. Eur. J. 2008; 14: 10603
• 28a Dorrestein P, Begley TP. Bioorg. Chem. 2005; 33: 136
• 28b Bruyneel F, Dive G, Marchand-Brynaert J. Org. Biomol. Chem. 2012; 10: 1834
• 29 Yadav A, Mathur P. Catal. Commun. 2014; 55: 1
• 30 Nagasawa HT, Gutmann HR, Morgan MA. J. Biol. Chem. 1959; 234: 1600
• 31a Barton DH. R, Wang T.-L. Tetrahedron Lett. 1994; 35: 5149
• 31b Suzuki H, Furusho Y, Higashi T, Ohnishi Y, Horinouchi S. J. Biol. Chem. 2006; 281: 824
• 31c Choi J.-K, Chang Y.-K, Hong SY. Tetrahedron Lett. 1988; 29: 1967
• 32a Młochowski J, Kloc K, Syper L, Inglot DA, Piasecki E. Liebigs Ann. Chem. 1993; 1239
• 32b Reich HJ, Renga JM, Reich IL. J. Am. Chem. Soc. 1975; 97: 5434
• 32c Giurg M, Kowal E, Muchalski H, Syper L, Młochowski J. Synth. Commun. 2009; 39: 251
• 33 Sun H.-B, Hua R, Yin Y. J. Org. Chem. 2005; 70: 9071
• 34 Wąsińska M, Korczewska A, Giurg M, Skarżewski J. Synth. Commun. 2015; 45: 143
• 35 Shavaleev NM, Scopelliti R, Gumy F, Bunzli J.-CG. Inorg. Chem. 2009; 48: 2908
• 36 Tikhonina NA, Timofeeva GI, Matrosov VI, Gilyarov VA, Kabachnik MI. Zh. Obshch. Khim. 1975; 45: 2414 ; Chem. Abstr. 1976, 84, 43949
• 37 Shavaleev NM, Scopelliti R, Gumy F, Bunzli J.-CG. Inorg. Chem. 2009; 48: 7937
• 38 Perez-Bolivar C, Takizawa S.-Y, Nishimura G, Montes VA, Anzenbacher P. Chem. Eur. J. 2011; 17: 9076 ; see also the Supporting Information
• 39 Sharma U, Kumar P, Kumar N, Kumar V, Singh B. Adv. Synth. Catal. 2010; 352: 1834
• 40 Hanzlik RP, Weller PE, Desai J, Zheng J, Hall LR, Slaughter DE. J. Org. Chem. 1990; 55: 2736
• 41 Othmen K, Boule P. J. Photochem. Photobiol. A: Chem. 1999; 121: 161
• 42 Suzuki HS, Ohnishi Y, Furusho Y, Sakuda S, Horinouchi S. J. Biol. Chem. 2006; 281: 36944
• 43 Hughes MA, Baggs MJ, al-Dulayymi J, Baird MS, Williams PA. Appl. Environ. Microbiol. 2002; 68: 4965
• 44 Jansze SM, Saggiomo V, Marcelis AT. M, Lutz M, Velders AH. Tetrahedron Lett. 2015; 56: 1060
• 45 Balkrishna SJ, Bhakuni BS, Chopra D, Kumar S. Org. Lett. 2010; 12: 5394