RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2015; 47(15): 2270-2280
DOI: 10.1055/s-0034-1380657
DOI: 10.1055/s-0034-1380657
paper
Selective Oxidation of 1-Tetralones to 1,2-Naphthoquinones with IBX and to 1,4-Naphthoquinones with Oxone® and 2-Iodobenzoic Acid
Weitere Informationen
Publikationsverlauf
Received: 21. Januar 2015
Accepted after revision: 26. März 2015
Publikationsdatum:
07. Mai 2015 (online)
Abstract
The preparation of naphthoquinones by oxidation of 1-tetralone derivatives is reported. 1,2-Naphthoquinones were prepared by oxidation with IBX and 1,4-naphthoquinones were prepared by oxidation using Oxone® and 2-iodobenzoic acid. The mechanistic pathways are also discussed.
Key words
selective oxidation - IBX - 1,2-naphthoquinones - 1,4-naphthoquinones - hypervalent iodine reagentsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380657.
- Supporting Information
-
References
- 1a Quideau S, Pouységu L. Org. Prep. Proced. Int. 1999; 31: 617
- 1b Scott JD, Williams RM. Chem. Rev. 2002; 102: 1669
- 1c Pouységu L, Deffieux D, Quideau S. Tetrahedron 2010; 66: 2235
- 1d Danishefsky SJ, Mazza S, McCurry P. J. Org.Chem. 1974; 39: 3610
- 1e Stavber S, Zupan M. Tetrahedron 1992; 48: 5875
- 1f Takuwa A, Kai R, Kawasaki KI, Nishigaichi Y, Iwamoto H. J. Chem. Soc., Chem. Commun. 1996; 703
- 2 Shearer MJ, Newman P. Thromb. Haemostasis 2008; 100: 530
- 3a Wu A, Duan Y, Harvey RG. Tetrahedron 2010; 66: 2111
- 3b Nicolaou KC, Montagnon T, Baran PS. Angew. Chem. Int. Ed. 2002; 41: 993
- 4 Huang W, Li J, Zhang W, Zhou Y, Xie C, Lou Y, Li Y, Wang J, Li J, Lu W. Bioorg. Med. Chem. Lett. 2006; 16: 1905
- 5 Dohi T, Nakae T, Takenaga N, Uchiyama T, Fukushima K, Fujioka H, Kita Y. Synthesis 2012; 44: 1183
- 6 Gelman DM, Perlmutter P. Tetrahedron Lett. 2009; 50: 39
- 7a Stang PJ, Zhdankin VV. Chem. Rev. 1996; 96: 1123
- 7b Kita Y, Takada T, Tohma H. Pure Appl. Chem. 1996; 68: 627
- 7c Varvoglis A. Tetrahedron 1997; 53: 1179
- 7d Kitamura T, Fujiwara Y. Org. Prep. Proced. Int. 1997; 29: 409
- 7e Kirschning A. Eur. J. Org. Chem. 1998; 11: 2267
- 7f Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
- 7g Tohma H, Kita Y. Adv. Synth. Catal. 2004; 346: 111
- 7h Moriarty RM. J. Org. Chem. 2005; 70: 2893
- 7i Wirth T. Angew. Chem. Int. Ed. 2005; 44: 3656
- 7j Ochiai M. Chem. Rec. 2007; 7: 12
- 8 Arman S. Tetrahedron Lett. 2009; 50: 4693
- 9 Gallen MJ, Goumont R, Clark T, Terrier F, Williams CM. Angew. Chem. Int. Ed. 2006; 45: 2929
- 10 Ojha LR, Kudugunti S, Maddukuri PP, Kommareddy A, Gunna MR, Dokuparthi P, Gottam HB, Botha KK, Parapati DR, Vinod TK. Synlett 2009; 117
- 11a Gennaro PD, Galli E, Bestetti G. Tetrahedron 1999; 55: 4467
- 11b Er S, Suh C, Marshak MP, Aspuru-Guzik A. Chem. Sci. 2015; 6: 885
- 11c Klaus D, Gerhard H, Eberhard A, Gisela L, Hartmut L. German Patent DE 3926747 A1 19910214, 1991
- 11d Ivashkina NV, Yakovleva EA, Ivanchikova ID, Moroz AA, Shvartsberg MS. Russ. Chem. Bull. 2005; 54: 1509
- 11e Harinath BB, Subba RN. V. Proc. Indian Acad. Sci. A 1967; 66: 301
- 11f Willam AR, Philip NJ, Martin JW. J. Org. Chem. 1963; 28: 1169
- 12a Mital A, Negi VS, Ramachandran U. Med. Chem. 2008; 4: 492
- 12b Mitchell LJ, Lewis W, Moody CJ. Green Chem. 2013; 15: 2830
- 12c Reichwagen J, Henning H, Jean-Pierre D, Andre DG, Henri B. Synthesis 2005; 3505
- 12d Bell F, Gibson JA, Wilson RD. J. Chem. Soc. 1956; 2335
- 12e Shi G, Schlosser M. Tetrahedron 1993; 49: 1445
- 12f Shi F, Tse MK, Beller M. Adv. Synth. Catal. 2007; 349: 303
- 12g Lyons J, Thomson RH. J. Chem. Soc. 1953; 2910
- 12h Thomson RH. J. Chem. Soc. 1950; 1737