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Synthesis 2006(9): 1405-1407
DOI: 10.1055/s-2006-926417
DOI: 10.1055/s-2006-926417
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Effective One-Pot Synthesis of 5-Hydroxy-1,4-naphthoquinone Derivatives
Further Information
Received
16 November 2005
Publication Date:
04 April 2006 (online)
Publication History
Publication Date:
04 April 2006 (online)
Abstract
In the presence of triethylamine, Diels-Alder reaction, involving decarboxylation-oxidation reaction of 3-hydroxy-2-pyrones with 1,4-benzoquinones gave 5-hydroxy-1,4-naphthoquinone derivatives in excellent to reasonable yields.
Key words
Diels-Alder reaction - oxidations - quinones - polycycles - tandem reaction
- 1
Inbaraj JJ.Chignell CF. Chem. Res. Toxicol. 2004, 17: 55 -
2a
Cai L.Wei G.Bijl P.Wu CD. J. Agric. Food Chem. 2000, 48: 909 -
2b
Gu J.-Q.Graf TN.Lee D.Chai H.-B.Mi Q.Kardono LBS.Setyowati FM.Ismail R.Riswan S.Farnsworth NR.Cordell GA.Pezzuto JM.Swanson SM.Kroll DJ.Falkinham JO.Wall ME.Wani MC.Kinghorn AD.Oberlies NH. J. Nat. Prod. 2004, 67: 1156 - 3
Tandon VK.Chhor RB.Singh RV.Rai S.Yadav DB. Bioorg. Med. Chem. Lett. 2004, 14: 1079 - 4
Couladouros EA.Strongilos AT. Eur. J. Org. Chem. 2002, 3341 -
5a
Boger DL.Huter O.Mbiya K.Zhang M. J. Am. Chem. Soc. 1995, 117: 11839 -
5b
Wulff WD.Su J.Tang P.-C.Xu Y.-C. Synthesis 1999, 415 -
5c
Xu Y.-C.Kohlman DT.Liang SX.Erikkson C. Org. Lett. 1999, 1: 1599 -
6a
Hauser FM.Rhee RP. J. Org. Chem. 1980, 45: 3061 -
6b
Hauser FM.Prasanna S. J. Org. Chem. 1982, 47: 383 -
7a
Crouse DJ.Wheeler MM.Goemann M.Tobin PS.Basu SK.Wheeler DMS. J. Org. Chem. 1981, 46: 1814 -
7b
Laatsch H. Liebigs Ann. Chem. 1985, 1847 -
7c
Barret R.Daudon M. Tetrahedron Lett. 1990, 31: 4871 -
8a
Komiyama T.Takaguchi Y.Tsuboi S. Tetrahedron Lett. 2004, 45: 6299 -
8b
Komiyama T.Takaguchi Y.Gubaidullin AT.Mamedov VA.Litvinov IA.Tsuboi S. Tetrahedron 2005, 61: 2541 -
8c
Komiyama T.Takaguchi Y.Tsuboi S. Heterocycles 2005, 66: 503 -
9a
Okamura H.Iwagawa T.Nakatani M. Tetrahedron Lett. 1995, 36: 5939 -
9b
Shimizu H.Okamura H.Iwagawa T.Nakatani M. Tetrahedron 2001, 57: 1903 -
10a
Jung ME.Node M.Pfluger RW.Lyster MA.Lowe JA. J. Org. Chem. 1982, 47: 1150 -
10b
Ahmed SA.Bardshiri E.Simpson TJ. J. Chem. Soc., Chem. Commun. 1987, 883 - 11
Warren JD.Lee VJ.Angier RB. J. Heterocycl. Chem. 1979, 16: 1617 - 12
Gupta S.Ali M.Alam MS. Phytochemistry 1993, 33: 723