F. Delattre et al. / Tetrahedron 60 (2004) 1557–1562
1561
H-3, H-4, H-5, H-6A,B), 3.95 (3H, s, –OCH3), 4.33–4.59
(6H, m, –OH6), 4.78–4.97 (7H, m, H-1), 5.54–6.07 (14H,
m, –OH2, OH3), 7.14 0(2H, d, J¼8.7 Hz, H meta/CO), 7.73
(1H, d, J¼7.4 Hz, H3 ), 7.89 (2H,d, J¼8.66 Hz, H ortho/
gen mit einer C,N-Doppelbindungen; Thieme: Stuttgart, 1991.
(b) Mangalagiu, I.; Druta, I.; Constantinescu, M.; Humelnicu,
I.; Petrovanu, M. Tetrahedron 1996, 52, 8853. (c) Druta, I.;
Dinica, R.; Bacu, E.; Humelnicu, I. Tetrahedron 1998, 54, 1081.
(d) Caprosu, M.; Olariu, I.; Mangalagiu, I.; Constantinescu,
M.; Petrovanu, M. Eur. J. Org. Chem. 1999, 3501. (e) De Bue,
G.; Nasielski, J. Bull. Soc. Chim. Belg. 1997, 106, 97. (f)
Padwa, A.; Austin, D. J.; Precedo, L.; Zhi, L. J. Org. Chem.
1993, 58, 1144. (g) Miki, Y.; Hachiken, H.; Takemura, S.
Heterocycles 1984, 22, 701. (h) Tsuge, O.; Kanemasa, S.;
Kuraoko, S.; Takenaka, S. Chem. Lett. 1984, 279. (i)
Katritzky, A. R.; Guofang, Q.; Baozhen, Y.; Hai-Ying, H.
J. Org. Chem. 1999, 64, 7614. (j) Georgescu, F.; Georgescu,
E. I.; Chiraleu, F.; Zugravescu, I. Rev. Roum. Chim. 1981,
26(6), 879. (k) Georgescu, F.; Georgescu, E. I.; Draghici, C.;
Caproiu, M. T. Rev. Roum. Chim. 1997, 42(3), 205. (l)
Marchalin, S.; Cvopova, K.; Pham-Huu, D. P.; Chudik, M.;
0
0
CO), 8.21 (1H, s, H6 ), 8.23 (2H, d, J¼6.1 Hz, H2 ), 8.40 (m,
0
0
1H, NH), 8.88 (2H, d, J¼6.1 Hz, H1 ), 9.03 (1H, s, H5 ), 9.82
0
(1H, d, J¼7.38 Hz, H4 ); 13C NMR (DMSO-d6, 100 MHz) d
ppm: 56.39 (–OCH3), 60.54, 60.75, 60.93 (C6), 71.05,
72.23–74.34 (C2, C3, C5), 82.02–82.70, 84.96 (C4), 102.62,
0
123.45 (C2 ), 126.22 (C6 ), 129.32 (C4 ), 132.30 (C7 ),
0
102.79, 103.05 (C1), 113.76 (C3 ), 114.77 (C8 ), 119.36 (C5),
0
0
0
0
0
146.52 (C1 ), 163.19 (NH–CO), 184.52 (CO-w); IR(KBr,
cm21) 3399 (OH free, NH), 2916 (C–H strech), 1618 (CO);
m/z (%): 1511 (MþNa, 100), 1489 (MþH, 20). Anal. calcd
for C64H85N3O37·6H2O: C, 48.15; H, 6.12; N, 2.63. Found:
C, 48.41; H, 6.25; N, 2.72.
4.1.7. N-(6A-Deoxy-b-cyclodextrin-6A-yl)-1-(aminocar-
bonyl)-3-(4-chlorobenzoyl)-7-pyridin-4-ylindolizine 9e.
1H NMR (DMSO-d6, d, J, Hz): 3.23–3.90 (42H, m, H-2,
H-4 H-3, H-5, H-6A,B), 4.20–4.57 (6H, m, –OH6), 4.76–
4.94 (7H, m, H-1), 5.51–5.99 (14H, m, –OH2, OH3), 7.64
(2H, d, J¼8.5 Hz, H meta/CO), 7.70 (1H, dd, J¼7.4 Hz,
Kozisek, J.; Svoboda, I.; Daıch, A. Tetrahedron Lett. 2001, 42,
5663.
¨
3. (a) Harell, N. B.; Doerge, R. F. J. Pharm. Sci. 1967, 56, 225.
(b) Grubin, J.; Vogalaer, H.; Inion, H.; Houben, C.; Lucchetti,
J.; Mahaux, J.; Rossels, G.; Peiren, M.; Clinet, M.; Polster, P.;
Chatelain, P. J. Med. Chem. 1993, 36, 1425. (c) Grubin, J.;
Descamp, H.; Chatelain, P. Eur. Pat. Appl. EP235111, 1987;
Chem. Abstr. 1988, 109, 6405b.
0
H3 ), 7.81 (2H, d, J¼8.5 Hz, H ortho/CO), 7.83 (2H, d,
0
0
J¼6.1 Hz, H2 ), 8.15 (01H, s, H6 ), 8.26 (1H, m, NH), 8.7
0
(2H, d, J¼6.1 Hz, H1 ), 8.94 (1H, s, H5 ), 9.87 (1H, d,
4. (a) Vlahovici, A.; Andrei, M.; Druta, I. J. Lumin. 2002, 96,
279. (b) Sonnenschein, H.; Hennrich, G.; Resch-Genger, U.;
Schulz, B. Dyes Pigments 2000, 46, 23. (c) Vlahovici, A.;
Druta, I.; Andrei, M.; Cotlet, M.; Dinica, R. J. Lumin. 1999,
82, 155.
0
J¼7.5 Hz, H4 ); 13C NMR (DMSO-d6, d): 60.42, 60.53,
60.82 (C6), 71.11, 72.76–74.04 (C2, C3, C5), 81.92, 82.05,
82.10, 82.48, 82.61, 82.87, 85.07 (C4), 102.71, 102.86,
0
0
0
103.12 (C1), 114.43 (C3 ), 117.86 (C5 ), 121.69 (C2 ), 127.06
0
0
0
0
0
(C6 ), 129.41 (C4 ), 129.46 (C8 ), 131.75 (C7 ), 151.49 (C1 ),
164.22 (NH–CO), 184.21 (CO-w); IR (KBr, cm21): 3397
(OH free, NH), 2918 (C–H strech), 1601 (CO); m/z (%):
1516 (MþNa, 32), 1514 (MþNa22). Anal. calcd for
C63H82ClN3O36·5H2O: C, 47.81; H, 5.86; N, 2.65. Found:
C, 48.02; H, 5.99; N, 2.84.
5. (a) Lehn, J. M. Supramolecular chemistry; VCH: Vergagsge-
sellshaft, 1995. (b) Czarnik, A. W. Fluorescent chemosensors
for ion and molecule recognition. ACS Symposium Series 538;
American Chemical Society: Washington, DC, 1992. (c)
Grynkiewicz, G.; Poenie, M.; Tsien, R. J. Biol. Chem. 1985,
260, 3440. (d) Fabrizzi, L.; Poggi, A. Chem. Soc. Rev. 1995,
24, 197. (e) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302. (f)
De Silva, A. P.; Gunaratne, H. Q. N.; McVeigh, C.; Maguire,
G. E. M.; Maxwell, P. R. S.; O’Hanlon, E. Chem. Commun.
1996, 2191. (g) Chen, C. T.; Wagner, H.; Still, W. C. Science
1998, 279.
4.1.8. N-(6A-Deoxy-b-cyclodextrin-6A-yl)-1-(aminocar-
bonyl)-3-(4-nitrobenzoyl)-7-pyridin-4-ylindolizine
9f.
1H NMR (DMSO-d6, d, J, Hz): 3.21–4.04 (42H, m, H-2,
H-3, H-4, H-5, H-6A,B), 4.42–4.71 (6H, m, –OH6), 4.80–
5.06 (7H, m, H-1), 5.72–6.01 (14H, m, –OH2, –OH3), 7.83
6. (a) De Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.;
Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E.
Chem. Rev. 1997, 97, 1515. (b) Prodi, L.; Bolleta, F.; Monalti,
M.; Zaccheroni, N. Coord. Chem. Rev. 2000, 205, 59. (c) De
Silva, A. P.; Fox, D. B.; Huxley, A. J. M.; Moody, T. S. Chem.
0
0
(1H, d, J¼7.5 Hz, H3 ), 7.92 (2H, d, J¼5.8 Hz, H2 ), 8.14
0
(2H, d, J¼8.5 Hz, H meta/CO), 8.22 (1H, s, H6 ), 8.47 (2H,
d, J¼8.5 Hz, H ortho/CO), 8.40 0(1H, m, NH), 8.80 (2H, d,
0
J¼05.8 Hz, H1 ), 9.02 (1H, s, H5 ), 9.98 (1H, d, J¼7.5 Hz,
H4 ); 13C NMR (DMSO-d6, d): 59.88, 60.42 (C6), 73.02,
73.56, 74.34 (C2, C3, C5), 80.53, 80.98, 81.37, 82.42 (C4),
´
Rev. 2000, 205, 41. (d) Granda Valdes, M.; Badia, R.; Pina
Luis, G.; Diaz-Garcia, M. E. Quim. Anal. 2000, 19, 1910. (e)
James, T. D.; Samankuramara Sandanayake, K. R. A.;
0
123.73 (C2 ), 124.51 (C6 ), 129.17 (C8 ), 130.82 (C4 ),
0
0
102.09, 102.38, 103.01 (C1), 115.39 (C3 ), 119.02 (C5 ),
0
0
0
¨
Shinkaı, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1910. (f)
Tong, A. J.; Yanauchi, A.; Hayashita, T.; Zang, A. Y.; Smith,
B. D.; Teramae, N. Anal. Chem. 2001, 73, 1530.
0
0
131.33 (C7 ), 151.53 (C1 ), 160.48 (NH–CO), 178.57 (CO-
w); IR (KBr, cm21): 3402 (OH free, NH), 2915 (C–H
strech), 1649 (CO); m/z (%): 1526 (MþNa, 100), 1504
(Mþ1, 30). Anal. calcd for C63H82N4O38·5H2O: C, 47.49;
H, 5.82; N, 3.52. Found: C, 47.76; H, 5.96; N, 3.61.
7. (a) Nakashima, H.; Takenka, Y.; Higashi, M.; Yoshida, N.
J. Chem. Soc., Perkin Trans. 2 2001, 2096. (b) Wagner, M.;
Engrand, P.; Regnouf-de-Vains, J. B.; Marsura, A. Tetra-
hedron Lett. 2001, 42, 5207. (c) Corradini, R.; Dossena, A.;
Galaverna, G.; Marchelly, R.; Paragia, A.; Sartor, G. J. Org.
Chem. 1997, 62, 6283. (d) Ueno, A.; Minato, I.; Suzuki, M.;
Osa, T. Anal. Chem. 1990, 62, 2461. (e) Ueno, A.; Suzuki, M.;
Fukushima, M.; Ohkubo, M.; Osa, T.; Hamada, F.; Murai, K.
Chem. Lett. 1990, 605. (f) McAlpine, S. R.; Garibay, M. A. G.
J. Am. Chem. Soc. 1996, 118, 2750. (g) Hubbard, B. K.;
Beisltein, L. A.; Heath, C. E.; Abelt, C. J. J. Chem. Soc.,
References and notes
1. Huisgen, R. 1,3-Dipolar cycloaddition chemistry; Padwa, A.,
Ed.; Wiley: New York, 1984; Vol. 1, pp 1–176.
2. (a) Houben, J.; Weyl, T. R. Organische Stickstoff-Verbindun-