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DOI: 10.1055/s-2005-861850
Oxidative Free Radical Cyclization of 2-(Ethoxycarbonylmethyl)-1,4-naphthoquinone Derivatives
Publication History
Publication Date:
09 March 2005 (online)

Abstract
A manganese(III)-mediated oxidative free radical cyclization of 2-(ethoxycarbonylmethyl)-1,4-naphthoquinone derivatives is described. These starting 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones can be synthesized effectively from the reaction of corresponding 1,4-naphthoquinones with ethyl nitroacetate. With 2-benzyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, naphthacene-5,12-diones were produced effectively in high selectivity. With ethyl 2-benzoyl-3-(ethoxycarbonylmethyl)-1,4-naphthoquinones, in addition to the expected 6-hydroxynaphthacene-5,12-diones, the novel naphtho[2,3-c]furan-4,9-diones were also formed as the major product.
Key words
manganese(III) acetate - oxidative - free radical - cyclization - 2-(ethoxycarbonylmethyl)-1,4-naphthoquinones
- 1a
Hart DJ. Science 1984, 223: 883 - 1b
Neumann WP. Synthesis 1987, 665 - 1c
Curran DP. Synthesis 1988, 417 - 1d
Curran DP. Synthesis 1988, 489 - 1e
Giese B.Kopping B.Göbel T.Dickhaut J.Thoma G.Kulicke KJ.Trach F. Org. React. 1996, 49: 301 - 1f
Bowman WR.Bridge CF.Brookes P. J. Chem. Soc., Perkin Trans. 1 2000, 1 - 1g
Zheng W. Tetrahedron 2001, 57: 7237 - 2a
Melikyan GG. Synthesis 1993, 833 - 2b
Iqbal J.Bhatia B.Nayyar NK. Chem. Rev. 1994, 94: 519 - 2c
Snider BB. Chem. Rev. 1996, 96: 3391 - 2d
Nair V.Panicker SB.Nair LG.George TG.Augustine A. Synlett 2003, 156 - 2e
Nair V.Balagopal L.Rajan R.Mathew J. Acc. Chem. Rev. 2004, 37: 21 - 3a
Kuntsmann MP.Mitscher LA. J. Org. Chem. 1966, 31: 2920 - 3b
Maehr H.Liu C.-M.Perrotta A.Smallheer JM.Williams TH.Blount JF. J. Antibiot. 1982, 35: 1627 - 3c
Hayakawa Y.Furihata K.Seto H.Otake N. Tetrahedron Lett. 1985, 26: 3471 - 3d
Hayakawa Y.Furihata K.Seto H.Otake N. Tetrahedron Lett. 1985, 26: 3475 - 4a
The Chemistry of The Quinoid Compounds
Patai S.Rappoport Z. Wiley; New York: 1988. - 4b
Thomson RH. Natural Occurring Quinones IV: Recent Advances Chapman & Hall; London: 1997. - 5a
Citterio A.Sebastiano R.Carvayal MC. J. Org. Chem. 1991, 56: 5335 - 5b
Cho I.-S.Muchowski JM. Synthesis 1991, 567 - 5c
Citterio A.Sebastiano R.Nicolini M. Tetrahedron 1993, 49: 7743 - 5d
Tanyeli C.Özdenirhen D.Sezen B. Tetrahedron 2002, 58: 9983 - 6a
Chuang C.-P.Wang S.-F. Tetrahedron Lett. 1994, 35: 4365 - 6b
Chuang C.-P.Wang S.-F. J. Chin. Chem. Soc. 1997, 44: 271 ; Chem. Abstr. 1997, 127, 190631t - 6c
Chuang C.-P.Wang S.-F. Tetrahedron 1998, 54: 10043 - 6d
Chuang C.-P.Wang S.-F. Heterocycles 1999, 50: 489 - 6e
Chuang C.-P.Wu Y.-L.Jiang M.-C. Tetrahedron 1999, 55: 11229 - 6f
Jiang M.-C.Chuang C.-P. J. Org. Chem. 2000, 65: 5409 - 6g
Wu Y.-L.Chuang C.-P.Lin P.-Y. Tetrahedron 2001, 57: 5543 - 6h
Tsai A.-I.Wu Y.-L.Chuang C.-P. Tetrahedron 2001, 57: 7829 - 6i
Tseng C.-C.Wu Y.-L.Chuang C.-P. Tetrahedron 2002, 57: 7625 - 7a
Jacobsen N.Torsell K. Acta Chem. Scand. 1973, 27: 3211 - 7b
Brown PM.Thomson RH. J. Chem. Soc., Perkin Trans. 1 1976, 997 - 7c
Citterio A.Arnoldi A.Minisci F. J. Org. Chem. 1979, 44: 2674 - 7d
Citterio A.Vismara E.Bernardi R. J. Chem. Res., Synop. 1983, 88 - 7e
Citterio A.Vismara E.Bernardi R. J. Chem. Res., Miniprint 1983, 876 - 7f
William DR.Clark MP. Tetrahedron Lett. 1998, 39: 7629 - 8
Aldersley MF.Chishti SH.Dean FM.Douglas ME.Ennis DS. J. Chem. Soc., Perkin Trans. 1 1990, 2163