10070
J. Hirano et al. / Tetrahedron 62 (2006) 10065–10071
1
Calcd for C H NO: C, 75.45; H, 5.70; N, 8.80. Found: C,
1.56 (1H, br s, H-1). FABMS m/z¼160.1 (M+H). Anal.
References and notes
1
0 9
7
5.28; H, 5.71; N, 8.84.
1. Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103,
4
419–4476.
. Gale, P. A. Coord. Chem. Rev. 2003, 240, 191–221.
. Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40,
2
3
4.1.6. 7-Methoxy-4-quinolone (5). Colorless needles.
Yield: 6.9%. Mp 219–220 C. H NMR (500 MHz,
ꢁ
DMSO-d ): d ppm 3.84 (3H, s, CH O–), 5.92 (1H, d,
1
4
86–516.
. Kang, J.; Kim, H. S.; Jang, D. O. Tetrahedron Lett. 2005, 46,
079–6082.
6
3
4
5
6
J¼7.3 Hz, H-3), 6.88–6.90 (2H, m, H-5, 8), 7.78 (1H, d,
6
J¼7.3 Hz, H-2), 7.97 (2H, dd, J¼0.9, 8.2 Hz, H-6), 11.48
. Gunnlaugsson, T.; Davis, A. P.; Hussey, G. M.; Tierney, J.;
Glynn, M. Org. Biomol. Chem. 2004, 2, 1856–1863.
. Gunnlaugsson, T.; Davis, A. P.; O’Brien, J. E.; Glynn, M. Org.
Lett. 2002, 4, 2449–2452.
(
for C H NO : C, 68.56; H, 5.18; N, 8.00. Found: C,
1H, br s, H-1). FABMS m/z¼176.1 (M+H). Anal. Calcd
10 9 2
6
8.43; H, 5.19; N, 7.96.
7
8
. Kim, S. K.; Yoon, J. Chem. Commun. 2002, 770–771.
. Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun.
4
4
.1.7. 7-Acetyl-4-quinolone (6). Colorless prisms. Yield:
ꢁ
.5%. Mp 290–291 C. H NMR (500 MHz, DMSO-d ):
6
1
2
001, 2556–2557.
. Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116,
397–9398.
d ppm 2.65 (3H, s, CH CO–), 6.09 (1H, d, J¼7.3 Hz,
3
9
H-3), 7.81 (1H, dd, J¼1.5, 8.4 Hz, H-6), 7.99 (1H, d,
J¼7.6 Hz, H-2), 8.11 (1H, d, J¼0.9 Hz, H-8), 8.17 (1H, d,
J¼8.5 Hz, H-5), 11.90 (1H, br s, H-1). FABMS m/z¼188.1
9
1
1
1
0. Aldakov, D.; Palacios, M. A.; Anzenbacher, P., Jr. Chem.
Mater. 2005, 17, 5238–5241.
1. Curiel, D.; Cowley, A.; Beer, P. D. Chem. Commun. 2005,
2
2. Wen, Z.-C.; Jiang, Y.-B. Tetrahedron 2004, 60, 11109–11115.
(
M+H). Anal. Calcd for C H NO : C, 70.58; H, 4.85; N,
11 9 2
7
.48. Found: C, 70.37; H, 4.91; N, 7.40.
36–238.
4
.2. Computational method
13. Kovalchuk, A.; Bricks, J. L.; Reck, G.; Rurack, K.; Schulz, B.;
Szumna, A.; Weibhoff, H. Chem. Commun. 2004, 1946–
1947.
14. Pohl, R.; Aldakov, D.; Kubat, P.; Jursikova, K.; Marquez, M.;
Anzenbacher, P., Jr. Chem. Commun. 2004, 1282–1283.
15. Xu, G.; Tarr, M. A. Chem. Commun. 2004, 1050–1051.
16. Aldakov, D.; Anzenbacher, P., Jr. Chem. Commun. 2003, 1394–
1395.
All calculations were carried out using Spartan’04(W). The
geometry optimizations were performed with B3LYP at the
6
gies, and atomic charges were estimated at single-point
calculations (B3LYP/6-311+G(d,p)) using the geometries
optimized at the B3LYP/6-31G(d) levels.
-31G(d) level. The HOMO levels, LUMO levels, total ener-
1
1
7. Wu, F.-Y.; Jiang, Y.-B. Chem. Phys. Lett. 2002, 355, 438–444.
8. Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler,
J. L. J. Am. Chem. Soc. 1999, 121, 10438–10439.
4
.3. Absorption and fluorescence studies
1
9. Zhang, X.; Guo, L.; Wu, F.-Y.; Jiang, Y.-B. Org. Lett. 2003, 5,
The absorption and corrected fluorescence emission spectra
were recorded using a JASCO V-530 UV–vis spectropho-
tometer and an F-6500 spectrofluorometer. All 4-QO deriv-
atives were dissolved in DMSO at a 10 mM concentration.
They were diluted to the appropriate concentrations with
2
667–2670.
0. Choi, K.; Hamilton, A. D. Angew. Chem., Int. Ed. 2001, 40,
912–3915.
2
3
2
2
1. Beer, P. D. Acc. Chem. Res. 1998, 31, 71–80.
2. Wu, J.-S.; Zhou, J.-H.; Wang, P.-F.; Zhang, X.-H.; Wu, S.-K.
Org. Lett. 2005, 7, 2133–2136.
CH CN and used for the measurements. The titration experi-
3
ments were performed by adding the anion solutions in
CH CN to the solutions of the 4-QO derivatives. For estima-
2
2
2
3. Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999,
1
3
21, 9463–9464.
4. Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem.
Soc., Perkin Trans. 2 1998, 2325–2327.
tion of the association constants, the absorbance data from
the titration experiments were treated by Rose–Drago
method.
5. Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew.
Chem., Int. Ed. 2002, 41, 3811–3814.
Acknowledgements
26. Wiskur, S. L.; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V.
Acc. Chem. Res. 2001, 34, 963–972.
This work was partially supported by the Research Fellow-
ships of the Japan Society for the Promotion of Science for
Young Scientists (J.H.). The authors thank Dr. Masanori
Inagaki and Dr. Mariko Aso of Kyushu University for their
help in the high-resolution FABMS measurements.
27. Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37,
649–652.
28. Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc.
1998, 120, 8533–8534.
29. Hirano, J.; Hamase, K.; Fukuda, H.; Tomita, T.; Zaitsu, K.
J. Chromatogr., A 2004, 1059, 225–231.
3
0. Hirano, J.; Hamase, K.; Akita, T.; Zaitsu, K. Anal. Sci. 2005,
21, x45–x46.
Supplementary data
3
1. Wilson, J. N.; Bunz, U. H. F. J. Am. Chem. Soc. 2005, 127,
4124–4125.
Changes in absorption and fluorescence emission spectra of
2
of the calculated structures are available. Supplementary
ꢀ
, 4, and 5 upon the addition of F , and Cartesian coordinates
32. Urano, Y.; Kamiya, M.; Kanda, K.; Ueno, T.; Hirose, K.;
Nagano, T. J. Am. Chem. Soc. 2005, 127, 4888–4894.
33. Gabe, Y.; Urano, Y.; Kikuchi, K.; Kojima, H.; Nagano, T. J. Am.
Chem. Soc. 2004, 126, 3357–3367.