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Synthesis 2004(13): 2131-2134
DOI: 10.1055/s-2004-829187
DOI: 10.1055/s-2004-829187
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Simple Synthesis of Angular Anthrathiophenediones via Acetylenic Derivatives of Anthraquinone
Further Information
Received
24 February 2004
Publication Date:
30 July 2004 (online)
Publication History
Publication Date:
30 July 2004 (online)
Abstract
Condensation of 2-alkynyl-1-chloro- and 1-alkynyl-2-chloroanthraquinones with Na2S under mild conditions afforded anthra[1,2-b]thiophene-6,11-diones and anthra[2,1-b]thiophene-6,11-diones, respectively. A variety of angular anthrathiophenediones was synthesized by this method. The acetylenic precursors were prepared by a modified procedure of the Sonogashira reaction.
Key words
quinones - alkynes - cross-coupling - ring closure - sulfur
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Kesteleyn B.De Kimpe N. Tetrahedron Lett. 2000, 41: 755 - 2
Kita Y.Kirihara M.Sekihachi J.Okunaka R.Sasho M.Mohri S.Honda T.Akai S.Tamura Y.Shimooka K. Chem. Pharm. Bull. 1990, 38: 1836 - 3
Ohba Y.Murakami Y.Sone T.Awano H. J. Heterocycl. Chem. 1997, 34: 781 - 4
Deng X.Liebeskind LS. J. Am. Chem. Soc. 2001, 123: 7703 - 5
McDonald FE.Burova SA.Huffman LG. Synthesis 2000, 970 - 6
Yue D.Larock RC. J. Org. Chem. 2002, 67: 1905 - 7
Piskunov AV.Shvartsberg MS. Mendeleev Commun. 1995, 155 - 8
Shvartsberg MS.Ivanchikova ID.Lebedeva NI. Tetrahedron Lett. 2000, 41: 5757 - 9
Shvartsberg MS.Barabanov II.Fedenok LG. Mendeleev Commun. 1997, 98 - 10
Shvartsberg MS.Ivanchikova ID. Tetrahedron Lett. 2000, 41: 771 - 11
Barabanov II.Ivanchikova ID.Shvartsberg MS. Mendeleev Commun. 2000, 188 - 12
Fedenok LG.Barabanov II.Ivanchikova ID. Tetrahedron 2001, 57: 1331 - 13
Flynn BL.Verdier-Pinard P.Hamel E. Org. Lett. 2001, 3: 651 - 14
Malte AM.Castro CE. J. Am. Chem. Soc. 1967, 89: 6770 - 15
Lendel VG.Pakh VJ.Petrus VV.Kijak MY.Migalina YV. Khim. Geterotsikl. Soedin. 1990, 1331 - 16
Smirnov-Zamkov IV.Zborovsky YL. Zh. Organ. Khim. 1977, 667 - 17
Sakamoto T.Kondo Y.Watanabe R.Yamanaka H. Chem. Pharm. Bull. 1986, 34: 2719 - 18
Gorelik MV. Chemistry of Antraquinones and Their Derivatives Khimiya; Moscow: 1983. p.296 - 19
Piskunov AV.Moroz AA.Shvartsberg MS. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1986, 35: 785 - 20
Piskunov AV.Moroz AA.Shvartsberg MS. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1987, 36: 755 - 21
Shvartsberg MS.Piskunov AV.Moroz AA. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1990, 39: 987 - 22
Dokunikhin NS.Kolokolov BN. Zh. Vses. Khim. Obshchstva im D.I. Mendeleeva 1963, 8: 710 ; Chem. Abstr. 1964, 60, 9216