3656
G. E. Collis, A. K. Burrell / Tetrahedron Letters 46 (2005) 3653–3656
15. The 1H, 13C NMR and melting point of this compound is
in agreement with that of the TCI sample.
References and notes
1
16. Selected data for 10-HBQ (1); mp 101–102 °C, H NMR
(300 MHz, DMSO-d6) d 14.82 (s, 1H, OH); 8.99 (dd, 1H,
J = 4.7, 1.6 Hz, H2); 8.59 (dd, 1H, J = 8.1, 1.6 Hz, H4);
7.96 (A part of ABq, 1H, J = 8.9 Hz, H6); 7.88 (B part of
ABq, 1H, J = 8.9 Hz, H5); 7.80 (dd, 1H, J = 8.1, 4.7 Hz,
H3); 7.66 (app t, 1H, H8); 7.52 (br d, 1H, J = 7.8 Hz, H7);
7.16 (dd, 1H, J = 7.8, 0.9 Hz, H9). 13C NMR (75.5 MHz,
DMSO-d6) d 158.7, 147.2, 145.9, 137.1, 134.7, 129.9, 128.7,
125.9, 125.1, 121.7, 118.1, 115.0, 113.3.
1. Eisenbud, E. Appl. Occup. Environ. Hyg. 1998, 13, 25;
Saltini, C.; Amicosante, M.; Franchi, A.; Lombardi, G.;
Richeldi, L. Eur. Resp. J. 1998, 12, 1463; Rossman, M. D.;
Preuss, O. P.; Powers, M. B. Beryllium: Biomedical
and Environmental Aspects; Williams and Wilkens: Balti-
more, 1991.
2. Chou, P.-T.; Wei, C.-Y. J. Phys. Chem. 1996, 100, 17059;
Roberts, E. L.; Chou, P. T.; Alexander, T. A.; Agbaria, R.
A.; Warner, I. M. J. Phys. Chem. 1995, 99, 5431.
3. Hamada, Y.; Sano, T.; Fujita, M.; Fujii, T.; Nishio, Y.;
Shibata, K. Chem. Lett. 1993, 905.
17. Although a synthesis for this compound has been cited, it
contains no experimental or characterization data; Tula-
gin, V.; Coles, R. F. Chem. Abstr. 1957, 914.
4. Matsumiya, H.; Hoshino, H.; Yotsuyanagi, T. Analyst
2001, 126, 2082.
1
18. Selected data for 7-HBQ (9); mp 254 °C decomposes, H
NMR (300 MHz, DMSO-d6) d 10.29 (br s, 1H, OH); 8.98
(dd, 1H, J = 4.3, 1.7 Hz, H2); 8.65 (d, 1H, J = 8.2 Hz,
H10); 8.38 (dd, 1H, J = 8.0, 1.7 Hz, H4); 8.18 (d, 1H,
J = 9.1 Hz, H6); 7.78 (d, 1H, J = 9.1 Hz, H5); 7.65 (dd,
1H, J = 8.0, 4.3 Hz, H3); 7.54 (app t, 1H, H9); 7.15 (dd,
1H, J = 7.7, 1.0 Hz, H8). 13C NMR (75.5 MHz, DMSO-
d6) d 153.5, 148.9, 145.6, 136.0, 132.3, 127.5, 126.1, 123.9,
123.4, 122.2, 121.4, 114.5, 111.8.
5. Schenkel-Rudin, H.; Schenkel-Rudin, M. Helv. Chim.
Acta 1944, 27, 1456.
6. (a) Chou, P.-T.; Wu, G.-R.; Liu, W.-S.; Chiou, C.-S. J.
Phys. Chem. A 2002, 106, 5967; (b) Collis, G. E.; Burrell,
A. K., unpublished results.
7. Correct IUPAC nomenclature for (4) is 7,8-didehydro-
quinoline, but the name commonly used is 7,8-quinolyne.
8. Kauffmann, T.; Udluft, K. Angew. Chem. 1963, 75,
89.
9. Fleming, I.; Mah, T. J. Chem. Soc., Perkin Trans. 1 1976,
1577.
19. Kubicki, M.; Borowiak, T. Acta Crystallogr. 1951, C51,
1173.
20. Maggiani, A.; Tubul, A.; Brun, P. Tetrahedron Lett. 1998,
39, 4485.
10. Lee, Y.-H.; Seo, J.; Yoon, I.; Park, K.-M.; Lee, S. S. Anal.
Sci. 2001, 17, 805.
´
´
21. Rebstock, A.-S.; Mongin, F.; Trecourt, F.; Queguiner, G.
Org. Biomol. Chem. 2004, 2, 291.
11. Giles, R. G. F.; Hughes, A. B.; Sargent, M. V. J. Chem.
Soc., Perkin Trans. 1 1991, 1581.
22. (a) Benzo[g]quinoline-5,10-dione: Okunade, A. L.; Clark,
A. M.; Hufford, C. D.; Oguntimein, B. O. Planta Med.
1999, 65, 447; (b) Benzo[g]isoquinoline-5,10-dione: Solis,
P. N.; LangÕat, C.; Gupta, M. P.; Kirby, G. C.; Warhurst,
D. C.; Phillipson, J. P. Planta Med. 1995, 61, 62.
23. Collis, G. E.; Wege, D. Aust. J. Chem. 1997, 50, 505.
24. Selected data for (16); mp 134 °C, 1H NMR (300 MHz,
CDCl3) d 14.49 (s, 1H, OH); 8.85 (dd, 1H, J = 4.6, 1.7 Hz,
H2); 8.30 (d, 1H, J = 9.1 Hz, H6); 8.27 (dd, 1H, J = 8.0,
1.7 Hz, H4); 7.66 (d, 1H, J = 9.1 Hz, H5); 7.59 (dd, 1H,
J = 8.0, 4.6 Hz, H3); 7.19 (A part of ABq, 1H, J = 8.6 Hz,
H9); 7.14 (B part of ABq, 1H, J = 8.6 Hz, H8); 4.01 (s, 3H,
OMe).
12. Jung, K.-Y.; Koreeda, M. J. Org. Chem. 1989, 54,
5667.
13. Gershon, H.; McNeil, M. W.; Grefig, A. T. J. Org. Chem.
1969, 34(11), 3268.
14. Selected data for endoxide (8); mp 115 °C, 1H NMR
(300 MHz, CDCl3) d 8.86 (dd, 1H, J = 4.1, 1.6 Hz, H2);
8.12 (dd, 1H, J = 8.4, 1.6 Hz, H4); 7.59 (A part of ABq,
1H, J = 7.8 Hz, H6); 7.55 (B part of ABq, 1H, J = 7.8 Hz,
H5); 7.33–7.25 (m, 2H, H3 and 8); 7.20 (dd, 1H, J = 5.5,
1.8 Hz, H9); 6.54 (br s, 1H, H7); 5.95 (br s, 1H, H10). 13
C
NMR (75.5 MHz, CDCl3) d 153.2, 150.9, 148.8, 144.4,
144.2, 142.0, 136.7, 126.7, 125.8, 120.5, 119.9.