Y. Yang et al. / Tetrahedron Letters 48 (2007) 3505–3509
3509
3
˚
under reduced pressure. The residue was dissolved in
dichloromethane (10 mL) and added dropwise into a
solution of triethylamine (0.2 g, 2 mmol) and acetohyd-
razide (0.15 g, 2 mmol) in CH2Cl2 (10 mL) over a period
of 30 min with ice-water bath equipped. After complete
addition, the ice-water bath was removed. The reaction
mixture was stirred at room temperature for another 2 h,
and more CH2Cl2 (30 mL) added. The solution was
washed with diluted 2 N HCl (20 mL), saturated Na2CO3
aqueous solution (20 mL), and saturated brine (20 mL)
successively. The organic layer was dried over anhydrous
Na2SO4. After the solvent was evaporated under reduced
pressure, the crude product was recrystallized from
methanol to give product 4 (0.367 g, 99.7% yield) as a
white solid. Mp: 158–159 ꢁC. 1H NMR (300 MHz,
DMSO-d6, ppm): d 10.33 (d, J = 3.6 Hz, 2H, H–N), 9.86
(d, J = 3.6 Hz, 2H, H–N), 7.82 (d, J = 8.5 Hz, 2H, H-Ar),
6.68–6.65 (m, 4H, H-Ar), 4.21–4.16 (m, 8H, CH2), 3.80–
3.76 (m, 8H, CH2), 3.58–3.48 (m, 12H, CH2), 3.32–3.33
(m, 4H, CH2), 1.92 (s, 6H, COCH3). 13C NMR (75 MHz,
DMSO-d6, ppm): d 164.9, 160.6, 160.2, 156.0, 130.6, 111.0,
105.1, 98.3, 68.1, 68.0, 67.7, 66.9, 66.6, 66.5, 65.7, 18.4. IR
(KBr, cmꢁ1): 3211.9, 2937.1, 1655.6, 1605.5, 1261.2. MS
(ESI): m/z 737 [M+H]+, 759 [M+Na]+. Elemental Anal.
Calcd for C34H48N4O14ÆH2O: C, 54.10; H, 6.68; N, 7.42.
Found: C, 53.83; H, 6.55; N, 7.33.
76.503(4)ꢁ, c = 71.592(4)ꢁ, U = 2057.5(8) A , Z = 2,
Dc = 1.283 Mg/m3, T = 293(2) K, l = 0.100 mmꢁ1, 7205
reflections measured, 3206 unique (Rint = 0.0260), R1 =
0.0724, wR2 = 0.1942.
17. Crystal data for 4Æ5 (CCDC 608204): C49H68F12N6O15P2,
Mw = 1271.03, crystal size: 0.22 · 0.18 · 0.16 mm3, crystal
ꢀ
˚
system: triclinic, space group: Pð1Þ, a = 11.045(2) A, b =
˚
˚
17.257(7) A, c = 17.451(8) A, a = 75.946(16)ꢁ, b =
3
˚
75.316(19)ꢁ, c = 77.803(14)ꢁ, U = 3081.5(19) A , Z = 2,
Dc = 1.370 Mg/m3,
T = 294(2) K,
l = 0.172 mmꢁ1
,
10,174 reflections measured, 5102 unique (Rint = 0.0510),
R1 = 0.1371, wR2 = 0.3729.
18. For nomenclature, see: (a) Etter, M. C. Acc. Chem. Res.
1990, 23, 120–126; (b) Etter, M. C.; Macdonald, J. C.;
Bernstein, J. Acta Crystallogr., Sect. B. 1990, 46, 256–262;
(c) Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L.
Angew. Chem., Int. Ed. Engl. 1995, 34, 1555–1573.
19. Gibson H.W. et al. recently reported water assisted
formation of a dimeric structure and formation of a
dimeric structure driven by dipole–dipole and face-to-face
p-stacking interactions. (a) Huang, F.; Zakharov, L. N.;
Rheingold, A. L.; Jones, J. W.; Gibson, H. W. Chem.
Commun. 2003, 2122–2123; (b) Huang, F.; Zhou, L.;
Jones, J. W.; Gibson, H. W.; Ashraf-Khorassani, M.
Chem. Commun. 2004, 2670–2671.
20. (a) Jurecˇka, P.; Hobza, P. J. Am. Chem. Soc. 2003, 125,
15608–15613; (b) Da˛bkowska, I.; Gonzalez, H. V.;
Jurecˇka, P.; Hobza, P. J. Phys. Chem. A. 2005, 109,
1131–1136; (c) Guo, D.; Sijbesma, R. P.; Zuilhof, H. Org.
Lett. 2004, 6, 3667–3670.
21. Huang et al. recently reported a supramolecular poly(tacꢁo
complex), in which hydrogen bonding of the PF6
counterions with the urethane linkages of the guest played
a key role. See Ref. 4c.
14. Tsukube, H.; Furuta, H.; Odani, A.; Takeda, Y.; Kudo,
Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K. In
Comprehensive Supramolecular Chemistry; Atwood, J. L.,
Davies, J. E. D., MacNicol, D. D., Vogtle, F., Lehn,
J.-M., Eds.; Elsevier: New York, 1996; Vol. 8, p 425.
15. Similar [3]complexes reported by Huang et al. from
BMP32C10 based cryptands and paraquat, see: (a)
Huang, F.; Gibson, H. W.; Bryant, W. S.; Nagvekar, D.
S.; Fronczek, F. R. J. Am. Chem. Soc. 2003, 125, 9367–
9371; (b) Huang, F.; Lam, M.; Mahan, E. J.; Rheingold,
A. L.; Gibson, H. W. Chem. Commun. 2005, 3268–3270.
16. Crystal data for compound 4 (CCDC 608205): C37H54-
N4O15, Mw = 794.84, crystal size: 0.30 · 0.30 · 0.20 mm3,
ꢁ
22. Examples of PF6 anion assisted the assemblies in the
solid state, see: (a) Ashton, P. R.; Cantrill, S. J.; Preece, J.
A.; Stoddart, J. F.; Wang, Z.-H.; White, A. J. P.; Williams,
D. J. Org. Lett. 1999, 1, 1917–1920; (b) Fyfe, M. C. T.;
Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.;
Williams, D. J. Angew. Chem., Int. Ed. 1997, 36, 2068–
2070.
ꢀ
˚
crystal system: triclinic, space group: Pð1Þ, a = 9.758(2) A,
˚
˚
b = 13.528(3) A, c = 17.004(4) A, a = 79.685(4)ꢁ, b =