1312
D. T. Gryko et al.
LETTER
Sykes, T. R.; Noujaim, A. A. Synthesis 1997, 1010. (h) Gok,
Y; Atalay, Y. J. Inclus. Phenom. Mol. 1997, 28, 287. (i)
Arnaud, N.; Picard, C.; Cazaux, L.; Tisnes, P. Tetrahedron
1997, 53, 13757. (j) Chekhlov, A.A.; Baulin, V.E.; Martynov,
I.V. Dokl. Acad. Nauk. 1998, 358, 74. (k) Solovev, V.P.;
Strakhova, N.N.; Kazachenko, V.P.; Solotnov, A. F.; Baulin,
V. E.; Raevsky, O. A.; Rudiger, V.; Eblinger, F.; Schneider,
H. J. Eur. J. Org. Chem. 1998, 7, 1379.
References and Notes
(1) (a) Sutherland, I. O. Chem. Soc. Rev. 1986, 15, 63. (b) Kimura,
E. J. Coord. Chem. 1986, 15, 1. (c) Kimura, E. Tetrahedron
1992, 48, 6175. (d) Kimura, E.; Sasada, S.; Shionoya, T.;
Koike, T.; Kurasaki, H.; Shiro, M. J. Biol. Inorg. Chem. 1997,
2, 74. (e) Bu, X. H.; Cao, X. C.; An, D. L.; Zhang, R. H.;
Thomas, C.; Kimura, E. J. Chem. Soc. Dalton 1998, 433.
(f) Bu, X. H.; An, D. L.; Cao,X. C.; Zhang, R. H.; Clifford, T.;
Kimura, E. J. Chem. Soc. Dalton 1998, 2247.
(2) (a) Gokel, G. W.; Korzeniowski, S. H. Macrocyclic Polyether
Synthesis; Springer, Berlin, 1982. (b) Bradshaw, J. S.;
Krakowiak, K. E.; Izatt, R. M. Aza-Crown Macrocycles,
Wiley, New York, 1993.
(11) Bunnet, J. F.; Davis G. T. J. Am. Chem. Soc. 1960, 82, 665.
(12) (a) Betts, R. L.; Hammett, L. P. J. Am. Chem. Soc. 1937, 59,
1568. (b) Jencks, W. P.; Carriudo J. J. Am. Chem. Soc. 1960,
82, 675. (c) De Feoand, R. J.; Strickler, P. D. J. Org. Chem.
1963, 28, 2915.
(13) General procedure: Sodium (230 mg, 10 mmol) was added
to 8anhydrous methanol (100 mL). Then the mixture was
cooled to 5 °C and the α,ω-diamine (10 mmol) and dimethyl
dicarboxylate (10 mmol) were added. This mixture was left at
ambient temperature over a period of 8 hours (or longer). Then
the solvent was evaporated together with a small amount of
silica gel and the residue was chromatographed on silica gel
using 0-10% mixtures of methanol in CH2Cl2 as eluants. All
new compounds afforded correct elemental analysis and
spectroscopic data. For example:1-Thia-7,9-dioxa-4,13-
diazacyclopentadecane-3,14-dione (17): mp 126-128°C; IR
(KBr): ν = 3297, 2911, 1666, 1647, 1554, 1440, 1312, 1180,
1138, 1074, 1022; 1H NMR (200 MHz, CDCl3): δ = 3.33 (s,
4H), 3.4-3.5 (m, 4H), 3.6-3.7 (m, 8H), 7.13 (bs, 2H); 13C NMR
(50 MHz, CDCl3): δ = 36.8, 39.3, 68.9, 69.5, 167.8; MS (EI)
m/z (%):44 (38.7), 70 (26.2), 85 (73.2), 86 (53.5), 87 (20.6),
88 (23.6), 130 (17.3), 157 (21.7), 173 (18.5), 216 (22.6), 219
(20.8), 262 (100) [M+]; HREIMS: calcd C10H18O4N2S [M+]
262.0987; found 262.0992; C10H18O4N2S (262): calcd C
45.79, H 6.92, N 10.68, S 12.22; found C 45.83, H 7.08, N
10.73, S 12.24. 1,16-Dithia-7,10,22,25-tetraoxa-4,13,19,28-
tetraazatriacontane-3,14,18,29-tetraone (25): mp 222-
224°C; IR (KBr): ν = 3264, 3062, 2878, 1645, 1558, 1142,
1104; 1H NMR (200 MHz, CF3COOD): δ = 3.7-3.9 (m, 16H),
3.9-4.0 (m, 16H); 13C NMR (50 MHz, CF3COOD): δ = 37.8,
42.8, 70.6, 71.8, 177.2; MS (LSIMS) m/z (%) :525 (39)
[MH+], 547 (4) [MNa+]; HRLSIMS: calcd C20H37O8N4S
[M+H+] 525.2053; found 525.2085; C20H36O8N4S2 (524):
calcd C 45.79, H 6.92, N 10.68, S 12.22; found C 46.04, H
7.20, N 10.47, S 12.31.
(3) Dietrich, B.; Lehn, J.-M.; Sauvage, J.-P. Tetrahedron Lett.
1969, 10, 2885.
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S. K.; Tetmas, R.; Weatherby, D. J. Chem. Soc., Chem.
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Stankiewicz, T.; Salanski, P.; Kasprzyk, S.; Lipkowski, P.
Tetrahedron 1993, 49, 1478.
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7957. (b) Lipkowski, P.; Gryko, D. T.; Jurczak, J.; Lipkowski,
J. Tetrahedron Lett. 1998, 39, 3833. (c) Gryko, D. T.; Piπtek,
P.; SalaÒski, P.; Jurczak, J. Tetrahedron: Asymm. 1998, 9,
1771. (d) Gryko, D. T.; Piπtek, P.; Pπcak, A.; PaÍys, M.;
Jurczak, J. Tetrahedron 1998, 54, 7505. (e) Gryko, D. T.;
Piπtek, P.; Jurczak, J. Synthesis 1999, 336.
(10) (a) Dierck, I.; Herman, G. G.; Goemine, A. M.; Van der Kelen,
G. P. Bull. Chem. Soc. Belg. 1993, 102 (1), 63. (b) Mason, A.;
Sutherland, I. O. J. Chem. Soc., Chem. Commun. 1994, 1131.
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Fukada, N.; Ohtsu, T.; Miwa, M.; Mashino, M.; Takeda, Y.
Bull. Chem. Soc. Jpn. 1996, 69, 1397. (e) Koike, T.; Inoue, M.;
Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 3091. (f)
Gok, Y. New J. Chem. 1996, 20, 971. (g) Moreau, P.; Tinkl,
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Maharajk, R. B.; Kwok, C. S.; Somayaji, V. V.; Peng, Z.;
Article Identifier:
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Synlett 1999, No. 8, 1310–1312 ISSN 0936-5214 © Thieme Stuttgart · New York