132
D. Saravanakumar et al. / Tetrahedron Letters 49 (2008) 127–132
(c) Gronert, S. J. Am. Chem. Soc. 1993, 115, 10258–
Supplementary data
10266.
14. (a) Amendola, V.; Boiocchi, D.; Colasson, B.; Fabbrizzi,
L. Inorg. Chem. 2006, 45, 6138–6147; (b) Boiocche, M.;
Boca, L. D.; Gomez, D. E.; Fabbrizzi, L.; Liccheli, M.;
Monzanic, E. Chem. Eur. J. 2005, 11, 3097–3104; (c)
Amendola, V.; Boiocchi, M.; Fabbrizzi, L.; Palchetti, A.
Chem. Eur. J. 2005, 11, 5648–5660; (d) Peng, X.; Wu, Y.;
Fan, J.; Tian, M.; Han, K. . J. Org. Chem. 2005, 70,
10524–10531; (e) Gunnlaugasson, T.; Kruger, P. E.;
Jensen, P.; Tierney, J.; Ali, H. D. P.; Hussey, G. M. J.
Org. Chem. 2005, 70, 10875–10878.
Supplementary data associated with this article can be
References and notes
1. (a) Amendola, V.; Esteban-Gomez, D.; Fabbrizzi, L.;
Licchelli, M. Acc. Chem. Res. 2006, 39, 343–353; (b) Beer,
P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486–
516.
15. Gayathri, D.; Velmurugan, D.; Ravikumar, K.; Sarava-
nakumar, D.; Kandaswamy, M. Acta Crystallogr. E 2007,
63, o2224–o2225.
16. (a) Selected data for receptor 1: C13H11N3O3: Yield: 1.09 g
(89%); mp: 180 ꢁC. Elemental Anal. Calcd: C, 60.70; H,
4.31; N, 16.33. Found: C, 60.69; H, 4.29; N, 16.32. EI mass
(m/z): 257 (M)+; IR (KBr, m cmÀ1): 3434 (OH), 3333 (NH),
1600 (C@N), 1496 (NO2). 1H NMR (400 MHz,
(CD3)2SO): d 11.65 (s, 1H), 10.64 (s, 1H), 8.50 (s, 1H),
8.14 (s, 1H), 8.03 (d, 2H, J = 8 Hz) 7.22 (t, 2H,
J = 7.8 Hz), 7.01 (d, 2H, J = 8.8 Hz), 6.76 (t, 1H,
J = 7 Hz); 13C NMR (100 MHz, (CD3)2SO): d 112.0,
116.3, 119.4, 121.2, 122.2, 124.4, 129.3, 132.4, 140.1, 144.5,
160.8. kmax (nm) in CH3CN: 348, 300, 232, 194; (b)
Selected data for receptor 2: C13H10N4O5: Yield: 1.23 g
(89%); mp: 254 ꢁC. Elemental Anal. Calcd: C, 51.66; H,
3.33; N, 18.54. Found: C, 51.66; H, 3.32; N, 18.54. EI mass
(m/z): 302 (M)+; IR (KBr, m cmÀ1): 3445 (OH), 3361 (NH),
1613 (C@N), 1471 (NO2). 1H NMR (400 MHz,
(CD3)2SO): d 11.78 (1H, s), 10.27 (s, 1H), 9.06 (1H, s),
8.38 (1H, s), 8.16 (1H, d, J = 9.2 Hz), 8.03 (1H, d,
J = 8 Hz), 8.16–8.28 (m, 4H); 13C NMR (100 MHz,
(CD3)2SO): d 112.1, 116.0, 119.3, 122.4, 123.2, 124.1,
129.3, 139.2, 145.4, 152.2, 161.1, 163.2. kmax (nm) in
CH3CN: 348, 301, 233, 192.
17. (a) Ahmed, I. T. Spectrochim. Acta Part A 2006, 65, 5–10;
(b) Lee, D. H.; Lee, H. Y.; Hong, J.-I. Tetrahedron Lett.
2002, 43, 7273–7276; (c) Fujii, A.; Ebata, T.; Mikami, N.
J. Phys. Chem. A 2002, 106, 8554–8560; (d) Gerhards, M.;
Unterberg, C.; Kleinermanns, K. Phys. Chem. Phys. 2000,
2, 5538–5544.
18. Varquez, M.; Fabbirizzi, L.; Taglietti, A.; Pedrido, R. M.;
Gonzalez-Noya, A. M.; Bermejo, M. R. Angew. Chem.,
Int. Ed. 2004, 43, 1962–1965.
2. (a) Geddes, C. D. Meas. Sci. Technol. 2001, 12, R53; (b)
Kleerekoper, M. Endocrinol. Metab. Clin. North Am. 1998,
27, 441–452; (c) Kirk, K. L. Biochemistry of Halogens and
Inorganic Halides; Plenum Press: New York, 1991.
3. (a) Xu, J.; Liu, K.; Di, D.; Shao, S.; Guo, Y. Inorg. Chem.
Commun. 2007, 10, 681–684; (b) Suksai, C.; Tuntulani, T.
Chem. Soc. Rev. 2003, 32, 192–202; (c) Wiskur, S. L.; Ait-
Haddou, H.; Lavigne, J. J. V.; Anslyn, E. Acc. Chem. Res.
2001, 34, 963–972; (d) Inouye, M. Color. Non-Text. Appl.
2000, 238–274; (e) Lohr, H. G.; Vogtle, F. Acc. Chem. Res.
1985, 18, 65–72.
4. Ghosh, T.; Maiya, B. G. J. Chem. Sci. 2004, 116, 17–20.
5. (a) Duke, R. M.; Gunnlaugsson, T. Tetrahedron Lett.
2007, 48, 8043–8047; (b) Jose, D. A.; Kumar, D. K.;
Ganguly, B.; Das, A. Org. Lett. 2004, 6, 3445–3448.
6. Kim, H. J.; Lee, J. H.; Kim, T. H.; Lyoo, W. S.; Kim, D.
W.; Lee, C.; Lee, T. S. J. Polym. Sci. Part A: Polym.
Chem. 2007, 45, 1456–1546.
7. (a) Yu, M.; Lin, H.; Zhao, G.; Lin, H. J. Mol. Recognit.
2007, 20, 69–73; (b) Luxami, V.; Kumar, S. Tetrahedron
Lett. 2007, 48, 3083–3087; (c) Fabbrizzi, L.; Marcotte, N.;
Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41,
3809–3811.
8. (a) Lee, C.; Lee, D. H.; Hong, J.-I. Tetrahedron Lett. 2001,
42, 8665–8668; (b) Lee, K. H.; Lee, H.-Y.; Lee, D. H.;
Hong, J.-I. Tetrahedron Lett. 2001, 42, 5447–5449; (c) Lee,
D. H.; Lee, K. H.; Hong, J.-I. Org. Lett. 2001, 3, 5–8; (d)
Lee, D. H.; Lee, H. Y.; Lee, K. H.; Hong, J.-I. Chem.
Commun. 2001, 1188–1189; (e) Anzenbacher, P., Jr.; Try,
A. C.; Miyaji, H.; Jursikova, K.; Lynch, V. M.; Marquez,
M.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 10232–
10268.
19. Shao, S.; Guo, Y.; He, L.; Jiang, S.; Yu, X. Tetrahedron
Lett. 2003, 44, 2175–2178.
9. (a) Gale, P. A.; Twyman, L. J.; Handlin, C. I.; Sessler, J.
L. Chem. Commun. 1999, 1851–1852; (b) Niikura, K.;
Bisson, A. P.; Anslyn, E. V. J. Chem. Soc., Perkin Trans. 2
1999, 1111–1114.
20. (a) Descalzo, A. B.; Jimenez, D.; Marcos, M. D.;
Martinez-Manez, R.; Soto, J.; El Haskouri, J.; Guillem,
C.; Beltran, D.; Amoros, P.; Borrachero, M. V. Adv.
Mater. 2002, 14, 966–969; (b) Bargossi, C.; Fiorini, M. C.;
Montalti, M.; Prodi, L.; Zaccheroni, N. Coord. Chem.
Rev. 2000, 208, 17–32.
21. (a) Gunnlaugsson, T.; Kruger, P. E.; Jensen, P.; Pfefer, F.
M.; Hussey, G. M. Tetrahedron Lett. 2003, 44, 8909–8913;
(b) Carmiolo, S.; Gale, P. A.; Hursthouse, M. B.; Light,
M. E. Org. Biomol. Chem. 2003, 1, 741–744; (c) Shender-
ovich, I. G.; Tolstoy, P. M.; Golubev, N. S.; Smirnov, S.
N.; Denisov, G. S.; Limbach, H.-H. J. Am. Chem. Soc.
2003, 11710.
10. (a) Chen, C. F.; Chen, Q. Y. New J. Chem. 2006, 30, 143–
147; (b) Libra, E. R.; Scott, M. J. Chem. Commun. 2006,
1485–1487; (c) Channa, A.; Steed, A. W. Dalton Trans.
2005, 2455–2461; (d) Ghosh, S.; Choudhury, A. R.; Row,
T. N. G.; Maitra, U. Org. Lett. 2005, 7, 1441–1444; (e)
Lee, K. H.; Lee, H. Y.; Lee, D. H.; Hong, J.-I. Tetra-
hedron Lett. 2001, 42, 5447–5449; (f) Lee, C.; Lee, D. H.;
Hong, J.-I. Tetrahedron Lett. 2001, 42, 8665–8668.
11. Ghosh, T.; Maiya, B. G.; Wong, M. W. J. Phys. Chem. A.
2004, 108, 11249–11259.
22. (a) Miyaji, H.; Sato, W.; Sessler, J. L. Angew. Chem., Int.
Ed. 2001, 40, 154–157; (b) Black, C. B.; Andrioletti, B.;
Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc.
1999, 121, 10438–10439.
23. Hammud, H. H.; Ghannoum, A.; Masoud, M. S. Spectro-
chim. Acta Part A 2006, 63, 255–265.
12. (a) Boiocchi, M.; Del Boca, L.; Gomez, D. E.; Fabbrizzi,
L.; Licchelli, M.; Monazani, E. J. Am. Chem. Soc. 2004,
126, 16507–16514; (b) Gomez, D. E.; Fabbrizzi, L.;
Lichelli, M.; Monazani, E. Org. Biomol. Chem. 2005, 3,
1495–1507.
13. (a) Peng, X.; Wu, Y.; Fan, J.; Tian, M.; Han, K. J. Org.
Chem. 2005, 70, 10524–10531; (b) Gomez, D. E.; Fab-
brizzi, L.; Liccheli, M. J. Org. Chem. 2005, 70, 5717–5720;
24. Kato, R.; Nishizawa, S.; Hayashita, T.; Teramae, N.
Tetrahedron Lett. 2001, 42, 5053–5056.