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Synthesis 2015; 47(19): 2957-2960
DOI: 10.1055/s-0034-1381045
DOI: 10.1055/s-0034-1381045
special topic
Synthesis of Tribenzotropone by Ring Expansion of Phenanthrene-9,10-dione
Further Information
Publication History
Received: 15 April 2015
Accepted after revision: 05 June 2015
Publication Date:
07 August 2015 (online)
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Abstract
Tribenzotropone was efficiently synthesized by a ring-expansion method from readily available phenanthrene-9,10-dione via a ring-opened diketone as a key intermediate; the diketone was prepared by nucleophilic addition of allyl and vinyl groups, followed by an oxidative ring-opening reaction with lead(IV) acetate. Ring closure by an intramolecular Diels–Alder reaction and subsequent dehydrogenation produced tribenzotropone in 38% overall yield. Ring closure by a Morita–Baylis–Hillman reaction, on the other hand, produced a dibenzo-fused nonanedione in 22% overall yield.
Key words
annulations - cycloadditions - Diels–Alder reactions - fused-ring systems - ring expansionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1381045.
- Supporting Information
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References
- 1 Pauson PL. Chem. Rev. 1955; 55: 9
- 2 Mori A, Takeshita H. J. Am. Chem. Soc. 1990; 112: 8635
- 3 Mori A, Taya H, Takeshita H, Ujiie S. J. Mater. Chem. 1998; 8: 595
- 4 Hashimoto M, Ujiie S, Mori A. Adv. Mater. (Weinheim, Ger.) 2003; 15: 797
- 5 Stiles M, Libbey AJ. Jr. J. Org. Chem. 1957; 22: 1243
- 6 Bergman ED, Klein J. J. Org. Chem. 1958; 23: 512
- 7 Shukla D, Lukeman M, Shi Y, Wan P. J. Photochem. Photobiol., A 2002; 154: 93
- 8 Taljaard B, Taljaard JH, Imrie C, Caira MR. Eur. J. Org. Chem. 2005; 2607
- 9 Luo J, Song K, Gu F.l, Miao Q. Chem. Sci. 2011; 2: 2029
- 10 Udayakumar BS, Schuster GB. J. Org. Chem. 1993; 58: 4165
- 11 Dahnke KR, Paquette LA. Org. Synth. Coll. Vol. IX . Wiley; London: 1998: 181
- 12 Tochtermann W, Oppenländer K, Walter U. Chem. Ber. 1964; 97: 1329
- 13 Yeo JE, Yang X, Kim HJ, Koo S. Chem. Commun. 2004; 236
- 14 Do Y.-S, Sun R, Kim HJ, Yeo JE, Bae S.-H, Koo S. J. Org. Chem. 2009; 74: 917
- 15a Fallis AG. Can. J. Chem. 1984; 62: 183
- 15b Takao K.-i, Munakata R, Tadano K.-i. Chem. Rev. 2005; 105: 4779
- 15c Phillips AJ, Morris JC, Abell AD. Tetrahedron Lett. 2000; 41: 2723
- 16 Min J.-H, Jung S.-Y, Wu B, Oh JT, Lah MS, Koo S. Org. Lett. 2006; 8: 1459
For intramolecular Diels–Alder reactions with ring expansion, see: