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Synlett 2008(18): 2864-2868
DOI: 10.1055/s-0028-1083570
DOI: 10.1055/s-0028-1083570
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Azide-Mediated Detosylation of N-Tosylpyrroloiminoquinones and N-Tosylindole-4,7-quinones
Further Information
Received
28 April 2008
Publication Date:
21 October 2008 (online)
Publication History
Publication Date:
21 October 2008 (online)
![](https://www.thieme-connect.de/media/synlett/200818/lookinside/thumbnails/10.1055-s-0028-1083570-1.jpg)
Abstract
The utility of NaN3 as a reagent for the detosylation of N-tosylpyrroloiminoquinones and N-tosylindole-4,7-quinones is described. The NaN3-mediated detosylation is carried out in polar aprotic solvents such as DMF and DMSO. The reaction occurs under neutral, mild conditions and results in good to excellent yields of the detosylated quinones.
Key words
sodium azide - detosylation - quinones - indoloquinone - pyrroloiminoquinones.
- 1
Wuts PGM.Greene TW. Greene’s Protective Groups in Organic Synthesis Wiley-Interscience; Hoboken NJ: 2006. - 2
Murakami Y. Yakugaku Zasshi 1999, 119: 35 - 3
Hari Y.Kanie T.Miyagi T.Aoyama T. Synthesis 2006, 1249 - 4
Biolatto B.Kneeteman M.Paredes E.Mancini PME. J. Org. Chem. 2001, 66: 3906 - 5
Gilbert EJ.Chisholm JD.Van Vranken DL. J. Org. Chem. 1999, 64: 5670 - 6
Haskins CM.Knight DW. Tetrahedron Lett. 2004, 45: 599 - 7
Aubart KM.Heathcock CH. J. Org. Chem. 1999, 64: 16 - 8
Sadanandan EV.Cava MP. Tetrahedron Lett. 1993, 34: 2405 - 9
Kokoshka JM.Capson TL.Holden JA.Ireland CM.Barrows LR. Anti-Cancer Drugs 1996, 7: 758 - 10
Beneteau V.Pierre A.Pfeiffer B.Renard P.Besson T. Bioorg. Med. Chem. Lett. 2000, 10: 2231 - 11
Legentil L.Benel L.Bertrand V.Lesur B.Delfourne E. J. Med. Chem. 2006, 49: 2979 - 12
Legentil L.Lesur B.Delfourne E. Bioorg. Med. Chem. 2006, 16: 427 - 13
Antunes EM.Copp BR.Davies-Coleman MT.Samaai T. Nat. Prod. Rep. 2005, 22: 62 - 14
Cheng JF.Ohizumi Y.Walchli MR.Nakamura H.Hirata Y.Sasaki T.Kobayashi J. J. Org. Chem. 1988, 53: 4621 - 15
Barrows LR.Radisky DC.Copp BR.Swaffar DS.Kramer RA.Warters RL.Ireland CM. Anti-Cancer Drug Des. 1993, 8: 333 - 16
Chang LC.Otero-Quintero S.Hooper JN.Bewley CA. J. Nat. Prod. 2002, 65: 776 - 17
Harayama Y.Kita Y. Curr. Org. Chem. 2005, 9: 1567 - 18
Sadanandan EV.Pillai SK.Lakshmikantham MV.Billimoria AD.Culpepper JS.Cava MP. J. Org. Chem. 1995, 60: 1800 - 19
Kita Y.Tohma H.Inagaki M.Hatanaka K.Yakura T. J. Am. Chem. Soc. 1992, 114: 2175 - 20
Shinkre BA.Velu SE. Synth. Commun. 2007, 37: 2399 - 21
Shinkre BA.Raisch KP.Fan L.Velu SE. Bioorg. Med. Chem. Lett. 2007, 17: 2890 - 22
Shinkre BA.Raisch KP.Fan L.Velu SE. Bioorg. Med. Chem. 2008, 16: 2541 - 23
Beneteau V.Besson T. Tetrahedron Lett. 2001, 42: 2673