22
P. S. Addy et al. / Tetrahedron Letters 53 (2012) 19–22
10. Facchetti, A.; Marks, T. J.; Yan, H. PCT Int. Appl. 2008, WO.2008085942 A2
20080717.
CD spectroscopy, and viscosity measurements confirmed the DNA-
binding ability of the synthesized quinines. The mode of binding
was also shown to be intercalative.
11. These were prepared by O-alkylation of the substituted propargyl alcohols
with the bromides of the other arm of the ether in presence of NaH in THF.
12. (a) Richardson, W. H. In Oxidation in Organic Chemistry; Wiberg, K. B., Ed.;
Academic: New York, 1965. Part A, Chapter IV; (b) Ho, T.-L. Synthesis 1973, 347;
(c) Jacob, P., III; Callery, P. S.; Shulgin, A. T.; Castagnoli, N., Jr. J. Org. Chem. 1976,
41, 3627; (d) Hauser, F. M.; Prasanna, S. J. Am. Chem. Soc. 1981, 103, 6378; (e)
Godard, A.; Rocca, P.; Fourquez, J. M.; Rovera, J. C.; Marsais, F.; Queguiner, G.
Tetrahedron Lett. 1993, 34, 7919; (f) Kitahara, Y.; Nakahara, S.; Shimizu, M.;
Yonezawa, T.; Kubo, A. Heterocycles 1993, 36, 1909.
Acknowledgments
Department of Science and Technology, Govt. of India, is
thanked for a research grant and also for 400 MHz and X-ray facil-
ities under the IRPHA and FIST programmes. PSA is grateful to CSIR,
Govt. of India for a fellowship.
13. Controlled oxidation can give rise to monoquinone. This aspect is currently
under investigation.
14. Selected spectral data: For 4-(1,4-Dimethoxy-naphthalen-2-yl)-5,10-
dimethoxy-1,3-dihydro-anthra[2,3-c]furan (18): State: Yellow gummy mass;
Yield 67%; dH (200 MHz, CDCl3): 8.39–8.36 (2H, m), 8.29 (1H, s), 8.22–8.16 (2H,
m), 7.67–7.46 (4H, m), 6.85 (1H, s), 5.40 (2H, s), 5.06 (1H, d, J = 14 Hz), 4.91 (1H,
d, J = 14 Hz), 4.21 (3H, s), 3.54 (3H, s), 3.40 (3H, s); dC (50 MHz, CDCl3): 150.9,
150.0, 148.5, 145.9, 139.5, 137.5, 129.4, 128.7, 127.5, 126.6, 126.2, 125.9, 125.6,
125.4, 125.2, 124.9, 123.7, 123.5, 122.5, 122.3, 113.5, 105.9, 94.7, 73.5, 63.2,
61.2, 55.9; MS: m/z 467 [MH+]; HRMS: Calcd for C30H26O5+H+ 467.1859, found
467.1863.
Supplementary data
Supplementary data (Spectral data.) associated with this article
For 4-(2,5-Dimethoxy-phenyl)-5,8-dimethoxy-1,3-dihydro naphtha [2,3-
c]furan (19): State: White gummy mass; yield 93%; dH (400 MHz, CDCl3):
8.15 (1H, s), 7.28 (1H, s), 6.89–6.84 (3H, m), 6.75–6.68 (3H, m), 5.32 (2H, s),
4.96 (1H, d, J = 13 Hz), 4.84 (1H, d, J = 13 Hz), 3.99 (3H, s), 4.78 (3H, s), 3.65 (3H,
s), 3.43 (3H, s); dC (100 MHz, CDCl3): 153.0, 151.4, 150.6, 149.9, 138.7, 137.0,
132.6, 127.4, 114.9, 114.6, 113.2, 112.2, 111.3, 106.3, 103.3, 73.8, 73.4, 56.4,
56.3, 55.8, 55.7; MS: m/z 367 [MH+]; HRMS: Calcd for C22H22O5+H+ 367.1546,
found 367.1548.
References and notes
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c]furan-5,10-dione (22): State: Golden yellow crystal; mp: 215 °C; Yield 78%;
dH (400 MHz, CDCl3): 8.37 (1H, s), 8.34 (1H, d, J = 1.6 Hz), 8.29 (1H, d,
J = 1.6 Hz), 8.19–8.17 (1H, m), 8.12 (1H, dd, J = 7.6 Hz, 1.2 Hz), 7.89–7.74 (4H,
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