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Volumn 14, Issue 3, 2009, Pages 1013-1031

Brominated thiophenes as precursors in the preparation of brominated and arylated anthraquinones

Author keywords

Anthraquinone; Oxidative cycloaddition; Suzuki cross coupling; UV spectroscopy.

Indexed keywords

3 CHLOROPERBENZOIC ACID; 3-CHLOROPERBENZOIC ACID; ANTHRAQUINONE DERIVATIVE; BROMINE; CHLOROBENZOIC ACID DERIVATIVE; NAPHTHOQUINONE; THIOPHENE DERIVATIVE;

EID: 63449112673     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14031013     Document Type: Article
Times cited : (13)

References (50)
  • 1
    • 78049336512 scopus 로고
    • The infrared study of the valence bond C=O in polycyclic compounds
    • Josien, J.M.; Fuson, N. The infrared study of the valence bond C=O in polycyclic compounds. Bull. Soc. Chim. Fr. 1952, 389-397.
    • (1952) Bull. Soc. Chim. Fr , pp. 389-397
    • Josien, J.M.1    Fuson, N.2
  • 2
    • 33846185522 scopus 로고    scopus 로고
    • Experimental evidence for carbonyl-π electron cloud interactions
    • Gautrot, J.E.; Hodge, P.; Cupertino, D.; Helliwell, M. Experimental evidence for carbonyl-π electron cloud interactions. New J. Chem. 2006, 30, 1801-1807.
    • (2006) New J. Chem , vol.30 , pp. 1801-1807
    • Gautrot, J.E.1    Hodge, P.2    Cupertino, D.3    Helliwell, M.4
  • 3
    • 46549098634 scopus 로고
    • A facile synthesis of functionalized 9,10-anthracenediones via tosylate and triflate phenolic activation
    • Showalter, H.D.H.; Berman, E.M.; Johnson, J.L.; Hunter, W.E. A facile synthesis of functionalized 9,10-anthracenediones via tosylate and triflate phenolic activation. Tetrahedron Lett. 1985, 26, 157-160.
    • (1985) Tetrahedron Lett , vol.26 , pp. 157-160
    • Showalter, H.D.H.1    Berman, E.M.2    Johnson, J.L.3    Hunter, W.E.4
  • 4
    • 63449083697 scopus 로고    scopus 로고
    • Shcheglova, N.A.; Shigorin, D.N.; Dokunikhin, N.S. Characteristics of luminescence and absorption spectra of 1- and 2-alkyl- and arylanthraquinones in solutions. II. Luminescence spectra at 77 K. Zh. Fiz. Khim. 1966, 40, 1048-1055; [Chem. Abstr. 1966, 65, 9958b].
    • Shcheglova, N.A.; Shigorin, D.N.; Dokunikhin, N.S. Characteristics of luminescence and absorption spectra of 1- and 2-alkyl- and arylanthraquinones in solutions. II. Luminescence spectra at 77 K. Zh. Fiz. Khim. 1966, 40, 1048-1055; [Chem. Abstr. 1966, 65, 9958b].
  • 5
    • 63449141667 scopus 로고    scopus 로고
    • Shcheglova, N.A.; Shigorin, D.N.; Dokunikhin, N.S. Spectra of luminescence and absorption of α - and β - alkyl and aryl derivatives of anthraquinone in solutions. I. Absorption spectra of α - and β - alkyl and aryl derivatives of anthraquinone. Zh. Fiz. Khim. 1965, 39, 3039-3043; [Chem. Abstr. 1965, 64, 12058f].
    • Shcheglova, N.A.; Shigorin, D.N.; Dokunikhin, N.S. Spectra of luminescence and absorption of α - and β - alkyl and aryl derivatives of anthraquinone in solutions. I. Absorption spectra of α - and β - alkyl and aryl derivatives of anthraquinone. Zh. Fiz. Khim. 1965, 39, 3039-3043; [Chem. Abstr. 1965, 64, 12058f].
  • 6
    • 63449103732 scopus 로고    scopus 로고
    • Orser, D.A, General Electric Company, Schenectady, N.Y, USA Light-modulating medium for image projection apparatus. US Pat. 3764549, Oct. 9, 1973; [Chem. Abstr. 1973, 79, 141431j
    • Orser, D.A. (General Electric Company, Schenectady, N.Y., USA) Light-modulating medium for image projection apparatus. US Pat. 3764549, Oct. 9, 1973; [Chem. Abstr. 1973, 79, 141431j].
  • 7
    • 37049152403 scopus 로고
    • Phenylated phthalic acids and anthracene derivatives
    • Weizmann, C.; Bergmann, E.; Haskelberg, L. Phenylated phthalic acids and anthracene derivatives. J. Chem. Soc. 1939, 391-397.
    • (1939) J. Chem. Soc , pp. 391-397
    • Weizmann, C.1    Bergmann, E.2    Haskelberg, L.3
  • 8
    • 33947437118 scopus 로고
    • Successive diene addition and dehydrogenation in nitrobenzene solution without isolation of the hydroaromatic intermediate
    • Bergmann, E.; Haskelberg, L.; Bergmann, F. Successive diene addition and dehydrogenation in nitrobenzene solution without isolation of the hydroaromatic intermediate. J. Org. Chem. 1942, 7, 303-306.
    • (1942) J. Org. Chem , vol.7 , pp. 303-306
    • Bergmann, E.1    Haskelberg, L.2    Bergmann, F.3
  • 9
    • 0342505353 scopus 로고
    • Synthesis of the 1-,2-,3-,4-hydroxy isomers of benz[a]anthracene-7,12-dione, benz[a]anthracene, and 7,12-dimethylbenz[a]anthracene
    • Muschik, G.M.; Tomaszewski, J.E.; Sato, R.I. Synthesis of the 1-,2-,3-,4-hydroxy isomers of benz[a]anthracene-7,12-dione, benz[a]anthracene, and 7,12-dimethylbenz[a]anthracene. J. Org. Chem. 1979, 44, 2150-2153.
    • (1979) J. Org. Chem , vol.44 , pp. 2150-2153
    • Muschik, G.M.1    Tomaszewski, J.E.2    Sato, R.I.3
  • 10
    • 63449139044 scopus 로고    scopus 로고
    • Puchkov, V.A. Synthesis of 1-phenylanthraquinone.Zh. Vsesoy. Khim. Obshch. im. D. I. Mendeleeva 1961, 6, 238-239; [Chem. Abstr. 1961, 55, 19877g].
    • Puchkov, V.A. Synthesis of 1-phenylanthraquinone.Zh. Vsesoy. Khim. Obshch. im. D. I. Mendeleeva 1961, 6, 238-239; [Chem. Abstr. 1961, 55, 19877g].
  • 13
    • 63449137507 scopus 로고    scopus 로고
    • Thiemann, T.; Li, Y.Q.; Mataka, S.; Tashiro, M. Intramolecular oxidative cycloaddition of thiophenes. J. Chem. Res. (S) 1995, 384-384, (M) 1995, 2364-2379.
    • Thiemann, T.; Li, Y.Q.; Mataka, S.; Tashiro, M. Intramolecular oxidative cycloaddition of thiophenes. J. Chem. Res. (S) 1995, 384-384, (M) 1995, 2364-2379.
  • 15
    • 0007243634 scopus 로고    scopus 로고
    • Lewis acid catalysed oxidative cycloaddition of thiophenes
    • Li, Y.Q.; Matsuda, M.; Thiemann, T.; Sawada, T.; Mataka, S. Lewis acid catalysed oxidative cycloaddition of thiophenes. Synlett. 1996, 461-464.
    • (1996) Synlett , pp. 461-464
    • Li, Y.Q.1    Matsuda, M.2    Thiemann, T.3    Sawada, T.4    Mataka, S.5
  • 16
    • 0000314020 scopus 로고    scopus 로고
    • Lewis acid catalysis in the oxidative cycloaddition of thiophenes
    • Li, Y.Q.; Thiemann, T.; Sawada, T.; Mataka, S.; Tashiro, M. Lewis acid catalysis in the oxidative cycloaddition of thiophenes. J. Org. Chem. 1997, 62, 7926-7936.
    • (1997) J. Org. Chem , vol.62 , pp. 7926-7936
    • Li, Y.Q.1    Thiemann, T.2    Sawada, T.3    Mataka, S.4    Tashiro, M.5
  • 17
    • 0002167428 scopus 로고    scopus 로고
    • Li, Y.Q.; Thiemann, T.; Mimura, K.; Sawada, T.; Mataka, S.; Tashiro, M. Oxidative cycloaddition of thiophenophanes - [n](2,5)-parathiophenophane (n=8,10-12.14). [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane. Eur. J. Org. Chem. 1998, 1841-1850.
    • Li, Y.Q.; Thiemann, T.; Mimura, K.; Sawada, T.; Mataka, S.; Tashiro, M. Oxidative cycloaddition of thiophenophanes - [n](2,5)-parathiophenophane (n=8,10-12.14). [8](2,4)metathiophenophane and [2.2](2,5)parametathiophenophane. Eur. J. Org. Chem. 1998, 1841-1850.
  • 18
    • 0036655559 scopus 로고    scopus 로고
    • for reviews, see: Thiemann T.; Dongol, K.G. Thiophene-S-oxides. J. Chem. Res. (S) 2002, 303-308; (M) 2002, 701-708 and ref.18.
    • for reviews, see: Thiemann T.; Dongol, K.G. Thiophene-S-oxides. J. Chem. Res. (S) 2002, 303-308; (M) 2002, 701-708 and ref.18.
  • 20
    • 0000224451 scopus 로고    scopus 로고
    • Exceptions are strained thiophenes: Nakayama J.; Kuroda, K. Synthesis and reactivities of a highly strained thiophene with two fused four-membered rings, 1,2,4,5-tetahydrodicyclobuta[b,d]thiophene. J. Am. Chem. Soc. 1993, 115, 4612-4617 and ref. 21, 22.
    • Exceptions are strained thiophenes: Nakayama J.; Kuroda, K. Synthesis and reactivities of a highly strained thiophene with two fused four-membered rings, 1,2,4,5-tetahydrodicyclobuta[b,d]thiophene. J. Am. Chem. Soc. 1993, 115, 4612-4617 and ref. 21, 22.
  • 21
    • 37049141736 scopus 로고    scopus 로고
    • Thiophenes with very effective electron-donor substituents: Barker, J.M.; Huddleston, P.R.; Shutler, S.W. Preparation and reactions of 2,5-dimethoxythiophene. J. Chem. Soc., Perkin Trans. 1 1975, 2483-2484.
    • Thiophenes with very effective electron-donor substituents: Barker, J.M.; Huddleston, P.R.; Shutler, S.W. Preparation and reactions of 2,5-dimethoxythiophene. J. Chem. Soc., Perkin Trans. 1 1975, 2483-2484.
  • 22
    • 49649133710 scopus 로고
    • One-step ring enlargement of a thiophene to a thiepin
    • Wynberg, H.; Helder, R. One-step ring enlargement of a thiophene to a thiepin. Tetrahedron Lett. 1972, 3647-3650.
    • (1972) Tetrahedron Lett , pp. 3647-3650
    • Wynberg, H.1    Helder, R.2
  • 23
    • 84993867948 scopus 로고    scopus 로고
    • This is underscored by theoretical calculations, see, cf, Jursic, B.S, Coupe, D. AM1 semiempirical searching for suitable thiophene derivatives that will enable thiophenes to act as a diene in the Diels-Alder reactions. J. Heterocycl. Chem. 1995, 32, 483-489
    • This is underscored by theoretical calculations, see, cf.: Jursic, B.S.; Coupe, D. AM1 semiempirical searching for suitable thiophene derivatives that will enable thiophenes to act as a diene in the Diels-Alder reactions. J. Heterocycl. Chem. 1995, 32, 483-489.
  • 25
    • 0030849375 scopus 로고    scopus 로고
    • Synthesis, isolation, and full characterization of the parent thiophene 1,1-dioxide
    • Nakayama, J.; Nagasawa, H.; Sugihara, Y.; Ishii, A. Synthesis, isolation, and full characterization of the parent thiophene 1,1-dioxide. J. Am. Chem. Soc. 1997, 119, 9077-9078.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 9077-9078
    • Nakayama, J.1    Nagasawa, H.2    Sugihara, Y.3    Ishii, A.4
  • 26
    • 0000144460 scopus 로고    scopus 로고
    • Xray crystallographic analysis of 2,5-bis(diphenylmethylsilyl) thiophene monooxide and the Diels-Alder reaction of thiophene monooxide with dienophiles
    • Furukawa, N.; Zhang, S.-Z.; Horn, E.; Takahashi, S.; Sato, S.; Yokoyama, M.; Yamaguchi, K. Xray crystallographic analysis of 2,5-bis(diphenylmethylsilyl) thiophene monooxide and the Diels-Alder reaction of thiophene monooxide with dienophiles. Heterocycles 1998, 47, 793-809.
    • (1998) Heterocycles , vol.47 , pp. 793-809
    • Furukawa, N.1    Zhang, S.-Z.2    Horn, E.3    Takahashi, S.4    Sato, S.5    Yokoyama, M.6    Yamaguchi, K.7
  • 27
    • 0000257674 scopus 로고    scopus 로고
    • Thiophene 1- oxides. V. comparison of the crystal structures and thiophene ring aromaticity of 2,5-diphenylthiophene, its sulfoxide and sulfone
    • Pouzet, P.; Erdelmeier, I.; Ginderow, D.; Mornon, J.-P.; Dansette, P.M.; Mansuy, D. Thiophene 1- oxides. V. comparison of the crystal structures and thiophene ring aromaticity of 2,5-diphenylthiophene, its sulfoxide and sulfone. J. Heterocycl. Chem. 1997, 34, 1567-1574.
    • (1997) J. Heterocycl. Chem , vol.34 , pp. 1567-1574
    • Pouzet, P.1    Erdelmeier, I.2    Ginderow, D.3    Mornon, J.-P.4    Dansette, P.M.5    Mansuy, D.6
  • 28
    • 8244240892 scopus 로고
    • Thiophene S-oxides: Convenient preparation, first complete structural characterization and unexpected dimerization of one of them, 2,5-diphenylthiophene 1-oxide
    • Pouzet, P.; Erdelmeier, I.; Ginderow, D.; Mornon, J.-P.; Dansette, P.M.; Mansuy, D. Thiophene S-oxides: convenient preparation, first complete structural characterization and unexpected dimerization of one of them, 2,5-diphenylthiophene 1-oxide. J. Chem. Soc., Chem. Commun. 1995, 473-474.
    • (1995) J. Chem. Soc., Chem. Commun , pp. 473-474
    • Pouzet, P.1    Erdelmeier, I.2    Ginderow, D.3    Mornon, J.-P.4    Dansette, P.M.5    Mansuy, D.6
  • 29
    • 0001394819 scopus 로고
    • Diels-Alder reactions of thiophene oxides generated in situ
    • Torssell, K. Diels-Alder reactions of thiophene oxides generated in situ. Acta Chem. Scand., Ser. B 1976, 30, 353-357.
    • (1976) Acta Chem. Scand., Ser. B , vol.30 , pp. 353-357
    • Torssell, K.1
  • 30
    • 2542496245 scopus 로고    scopus 로고
    • Thiemann, T.; Sa e Melo, M.L.; Campos Neves, A.S.; Li; Y.Q.; Mataka, S.; Tashiro, M.; Geiβler, U.; Walton, D. Preparation and electrooxidative SO-extrusion of halogenated 7-thiabicyclo[2.2.1]heptene 7-oxides. J. Chem. Res. (S) 1998, 346-347.
    • Thiemann, T.; Sa e Melo, M.L.; Campos Neves, A.S.; Li; Y.Q.; Mataka, S.; Tashiro, M.; Geiβler, U.; Walton, D. Preparation and electrooxidative SO-extrusion of halogenated 7-thiabicyclo[2.2.1]heptene 7-oxides. J. Chem. Res. (S) 1998, 346-347.
  • 31
    • 33847085898 scopus 로고
    • Annulations with tetrachlorothiophene 1,1-dioxide
    • Raasch, M.S. Annulations with tetrachlorothiophene 1,1-dioxide. J. Org. Chem. 1980, 45, 856-867.
    • (1980) J. Org. Chem , vol.45 , pp. 856-867
    • Raasch, M.S.1
  • 32
    • 0000949030 scopus 로고
    • Addition-rearrangement reactions of halogenated thiophene dioxides with furans
    • Raasch, M.S. Addition-rearrangement reactions of halogenated thiophene dioxides with furans. J. Org. Chem., 1980, 45, 867-870.
    • (1980) J. Org. Chem , vol.45 , pp. 867-870
    • Raasch, M.S.1
  • 33
    • 37049113302 scopus 로고
    • A simple construction of the iceane skeleton via an intramolecular Diels-Alder reaction
    • Hamon, D.P.G.; Spurr, P.R. A simple construction of the iceane skeleton via an intramolecular Diels-Alder reaction. J. Chem. Soc., Chem. Commun. 1982, 372-373.
    • (1982) J. Chem. Soc., Chem. Commun , pp. 372-373
    • Hamon, D.P.G.1    Spurr, P.R.2
  • 35
    • 63449118057 scopus 로고    scopus 로고
    • Wraight, E.S. Some Newer Phys. Methods Struct. Chem., Proc. Symp. 1967, 67-67; [Chem. Abstr. 1969, 70, 62337u].
    • Wraight, E.S. Some Newer Phys. Methods Struct. Chem., Proc. Symp. 1967, 67-67; [Chem. Abstr. 1969, 70, 62337u].
  • 36
    • 0000344234 scopus 로고
    • Electronic spectra of monosubstituted anthraquinones and solvent effects
    • Yoshida, Z.; Takabayashi, F. Electronic spectra of monosubstituted anthraquinones and solvent effects. Tetrahedron 1968, 24, 933-943.
    • (1968) Tetrahedron , vol.24 , pp. 933-943
    • Yoshida, Z.1    Takabayashi, F.2
  • 37
    • 37049157581 scopus 로고
    • Spectra of anthraquinone derivatives
    • Peters, R.H.; Sumners, H. Spectra of anthraquinone derivatives. J. Chem. Soc. 1953, 2101-2110.
    • (1953) J. Chem. Soc , pp. 2101-2110
    • Peters, R.H.1    Sumners, H.2
  • 38
    • 1842738247 scopus 로고    scopus 로고
    • 10 and Lawesson's reagent; a new method for the synthesis of dithieno[3,2-b;2',3'-d]thiophenes
    • 10 and Lawesson's reagent; a new method for the synthesis of dithieno[3,2-b;2',3'-d]thiophenes. Tetrahedron Lett. 2004, 45, 3405-3407.
    • (2004) Tetrahedron Lett , vol.45 , pp. 3405-3407
    • cf1    Ertas, E.2    Ozturk, T.3
  • 39
    • 0028765079 scopus 로고
    • + ion exchanger or ultrasonic irradiation
    • see also
    • + ion exchanger or ultrasonic irradiation. J. Mol. Cat. 1994, 88, 377-383.
    • (1994) J. Mol. Cat , vol.88 , pp. 377-383
    • Goldberg, Y.1    Alper, H.2
  • 40
    • 0040651368 scopus 로고
    • Substitution reactions of 2-phenylthiophene
    • Gjoes, N.; Gronowitz, S. Substitution reactions of 2-phenylthiophene. Acta Chem. Scand. 1972, 26, 1851-1859.
    • (1972) Acta Chem. Scand , vol.26 , pp. 1851-1859
    • Gjoes, N.1    Gronowitz, S.2
  • 41
    • 0034118525 scopus 로고    scopus 로고
    • This reaction has been reported to proceed under YbCl3 catalysis: Fang, X, Warner, B.P, Watkin, J.G. Ytterbium trichloride-catalyzed Diels-Alder reactions of un-activated dienes. Synth. Commun. 2000, 30, 2669-2676. We have found that it proceeds also in the presence of EuCl3
    • 3.
  • 42
    • 63449095717 scopus 로고    scopus 로고
    • 3N), also see ref. [43].
    • 3N), also see ref. [43].
  • 43
    • 0036098831 scopus 로고    scopus 로고
    • Synthesis of functionalized cis-syn-cis triquinanes
    • for HCl
    • Kotha, S.; Manivannan, E. Synthesis of functionalized cis-syn-cis triquinanes. Ind. J. Chem., Sect. B 2002, 41B, 808-811 (for HCl).
    • (2002) Ind. J. Chem., Sect. B , vol.41 B , pp. 808-811
    • Kotha, S.1    Manivannan, E.2
  • 44
    • 63449101855 scopus 로고    scopus 로고
    • We used Ag2O in benzene as the oxidation agent as described for the oxidation of other hydroquinones to quinones. The reaction gives quantitative yields of 6,7-dimethyl-5,8-dihydro-1,4-naphthoquinone, when carried out at rt. Specifically for the transformation of 6,7-dimethyl-5,8- dihydronaphthalene-1,4-diol to 6,7-dimethyl-5,8-dihydro-1,4-naphthoquinone, the use of MnO2 in acetone has been described, also: ref, 43
    • 2 in acetone has been described, also: ref. [43].
  • 45
    • 32244433188 scopus 로고    scopus 로고
    • Low-valent niobium-mediated double activation of C-F/C-H bonds: Fluorene synthesis from o-arylated alpha,alpha,alpha-trifluorotoluene derivatives
    • cf., Fuchibe K.; Akiyama, T. Low-valent niobium-mediated double activation of C-F/C-H bonds: fluorene synthesis from o-arylated alpha,alpha,alpha-trifluorotoluene derivatives. J. Am. Chem. Soc. 2006, 128, 1434-1435.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 1434-1435
    • cf1    Fuchibe, K.2    Akiyama, T.3
  • 47
    • 34250544590 scopus 로고
    • Substituted benzoylbenzoic acids
    • Hofmann, A. Substituted benzoylbenzoic acids. Monatsh. Chem. 1915, 36, 805-824.
    • (1915) Monatsh. Chem , vol.36 , pp. 805-824
    • Hofmann, A.1
  • 48
    • 63449122254 scopus 로고
    • The synthesis of some monomethylanthracenamines
    • Castle, R.N.; Kudo, H.; Lee, M.L. The synthesis of some monomethylanthracenamines. Coll. Czech Chem. Commun. 1991, 56, 2269-2277.
    • (1991) Coll. Czech Chem. Commun , vol.56 , pp. 2269-2277
    • Castle, R.N.1    Kudo, H.2    Lee, M.L.3
  • 49
    • 63449108253 scopus 로고
    • (Seiko Epson Corp.), Method of distinguishing right from left contact lenses by coloring. JP Pat. 04011214, 1992
    • Mizuno, H.; Kubota S. (Seiko Epson Corp.), Method of distinguishing right from left contact lenses by coloring. JP Pat. 04011214, 1992; [Chem. Abstr. 1992, 116, 221636].
    • (1992) Chem. Abstr , vol.116 , pp. 221636
    • Mizuno, H.1    Kubota, S.2
  • 50
    • 63449132337 scopus 로고
    • Syntheses based on Diels-Alder condensations. I. 1-Methyl-4-arylanthraquinones
    • Ganushchak, N.I.; Dombrovskii, A.V.; Vislobitskaya, O.A. Syntheses based on Diels-Alder condensations. I. 1-Methyl-4-arylanthraquinones. Zh. Obshch. Khim. 1963, 33, 2532-2534.
    • (1963) Zh. Obshch. Khim , vol.33 , pp. 2532-2534
    • Ganushchak, N.I.1    Dombrovskii, A.V.2    Vislobitskaya, O.A.3


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