Nov-Dec 2007 Synthesis of Novel Benzo-Substituted Macrocyclic Schiff Bases Containing Two Triazole Rings
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1998, 174, 51.
[6] Fenton, D. E.; Okawa, H. Chem. Ber., 1997, 130, 433.
(s, 3H, CH3C6H2), 3.70 (s, 3H, OCH3), 4.21 (s, 4H, SCH2), 5.19
(s, 4H, OCH2), 7.09-7.77 (m, 14H, ArH's), 8.81 (s, 2H, CH=N),
9.04 ppm (s, 2H, triazole H' s); ms: m/z (%) 689 (M++1, 0.7),
685 (0.8), 632 (1.2), 551 (13.2), 323 (6.8), 313 (62), 239 (41),
171 (30), 129 (77), 72 (100). Anal. Calcd for C36H32N8O3S2
(688.84): C, 62.77; H, 4.68; N, 16.27. Found: C, 63.00; H, 4.60;
N, 16.40.
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Synthesis of Macrocycle: The Design of Selective Complexing Agents,
Wiley, NY, 1987, p. 53.
13,17,32,36-Dimetheno-3,27-diphenyl-15-methyl-37-meth-
oxy-12H,-18H,27H,31H-bis[1,2,4]triazolo[4,3-f:3,4-q]dibenzo-
[b,u]-1,23-dioxa-5,6,18,19-tetraaza-8,16-dithiacyclotricontin
(35b). With the use of the general procedure 6b and 29 gave
crude 35b which was crystallized from ethanol as colorless
[12] Guerriero, P.; Tamburini, S.; Vigato, P. A. Coord. Chem.
Rev., 1995, 139, 17.
°
1
crystals (76%), mp 155-157 C; H nmr (DMSO-d6): ꢀ 2.03 (s,
3H, CH3C6H2), 3.71 (s, 3H, OCH3), 4.32 (s, 4H, S-CH2), 5.24 (s,
4H, OCH2), 7.13-7.98 (m, 24H, ArH's), 9.15 ppm (s, 2H,
CH=N); 13C nmr (DMSO-d6): ꢀ 20.27 (CH3C6H2), 37.72 (S-
CH2), 62.50 (O-CH3), 65.30 (O-CH2), 113.75, 120.24, 121.49,
126.66, 127.13, 127.84, 128.02, 128.56, 128.64, 128.72, 128.89,
129.48, 129.89, 133.42, 134.89, 136.62, 145.73, 151.92, 153.52,
158.53, 161.18 ppm (Aromatic C's, triazole C's, CH=N); ms:
m/z (%) 840 (M+, 0.7), 837 (0.9), 811 (0.7), 797 (0.8), 558
(15.9), 381 (25.6), 280 (100). Anal. Calcd for C48H40N8O3S2
(841.04): C, 68.55; H, 4.79; N, 13.32. Found: C, 68.70; H, 4.80;
N, 13.10.
[13] Murray, K. S. In: A. G. Sikes (Ed.), Advances in Inorganic
Chemistry, vol. 43, Academic Press, S. Diego, USA, 1995, p.261.
[14] Cooper, S. R. In “Crown Compounds: Towards future
Applications'' ed. S.R. Cooper, VCH, United Kingdom, UK, 1992.
[15] Melson, G. A. (Ed.), Coordination Chemistry of Macrocyclic
Compounds, Plenium Press, New York, 1979.
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216-217, 55.
[17] Gokel, G. W. Comprehensive Supramolecular Chemistry,
Vol. 1, Elsevier Science Ltd., 1996.
[18] Vögtle, F. Comprehensive Supramolecular Chemistry, Vol.
2, Elsevier Science Ltd., 1996.
[19] Hamilton, A. D. In: A. R. Katritzky, C. W. Rees (Eds.),
Comprehensive Heterocyclic Chemistry, Vol. 7, Pergamon Press, 1984,
pp. 731–761.
[20] Gokel, G. W.; Freder, M. F.; In: Katritzky, A. R.; Rees, C.
W.; Scriven, E. F. V. (Eds.), Comprehensive Heterocyclic Chemistry II,
Vol. 9, Pergamon Press, 1996, pp. 863–892;
[21] Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D.
J. Chem. Rev. 1989, 89, 929–972.
[22] Habata, Y.; Akabori, S.; Bradshaw, J. S.; Izatt, R. M. Ind.
Eng. Chem. Res. 2000, 39 3465.
[23] Elwahy, A. H. M. J. Heterocycl. Chem. 2003, 40, 1.
[24] Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004,
104, 2723.
[25] Vigato, P. A.; Tamburini, S. Coord. Chem. Rev. 2004, 248,
1717.
[26] Bradshaw, J. S.; Krakowiak, K. E.; Tarbet, B. J.; Bruening,
R. L.; Biernat, J. F.; Bochenska, M.; Izatt, R. M.; Christensen, J. J. Pure
Appl. Chem. 1989, 61, 1619.
13,17,32,36-Dimetheno-3,27-diphenyl-34-methyl-38-meth-
oxy-12H,18H,31H,37H-bis[1,2,4]triazolo[4,3-f:3,4-q]dibenzo-
[b,u]-1,23-dioxa-5,6,18,19-tetraaza-8,16-dithiacyclotricontin
(36). With the use of the general procedure 2 and 31 gave crude
36 which was crystallized from ethanol as colorless crystals
°
(71%), mp 210-212 C; 1H nmr (DMSO-d6): ꢀ 1.99 (s, 3H,
CH3C6H2), 3.63 (s, 3H, OCH3), 4.42 (s, 4H, S-CH2), 5.22 (s, 4H,
OCH2), 7.07-7.94 (m, 24H, ArH's), 8.98 ppm (s, 2H, CH=N);
13C nmr (DMSO-d6): ꢀ 19.89 (CH3C6H2), 32.12 (S-CH2), 62.29
(O-CH3), 69.65 (O-CH2), 113.65, 119.97, 121.49, 126.52,
127.07, 127.78, 128.07, 128.61, 128.71,129.89, 129.89, 131.77,
133.64, 134.88, 136.20, 136.26, 136.77, 145.68, 151.88, 154.73,
158.28, 160.45 ppm (Aromatic C's, triazole C's, CH=N); ms:
m/z (%) 841 (M++1, 3.1), 656 (4%), 604 (12), 578 (49), 481
(8.6), 367 (20.8), 313(100), 239 (40.7), 69 (73). Anal. Calcd for
C48H40N8O3S2 (841.04): C, 68.55; H, 4.79; N, 13.32. Found: C,
68.50; H, 4.50; N, 13.00.
[27] Elwahy, A. H. M.; Abbas, A. A. Tetrahedron, 2000, 56,
885.
13,17,32,36-Dimetheno-3,27-diphenyl-15,34-dimethyl-37,38-
dimethoxy-12H,18H,31H,37H-bis[1,2,4]triazole[4,3-f:3,4-q]-
dibenzo[b,u]-1,23-dioxa-5,6,18,19-tetraaza-8,16-dithiacyclo-
tricontin (37). With the use of the general procedure 29 and 31
gave crude 37 which was crystallized from benzene/n-pentane as
colorless crystals (78%), mp 154 °C; 1H nmr (DMSO-d6): ꢀ 1.93,
2.09 (2s, 6H, CH3C6H2), 3.41, 3.70 (2s, 6H, OCH3), 4.32 (s, 4H,
SCH2), 5.20 (s, 4H, OCH2), 7.16-7.99 ppm (m, 22H, ArH's),
9.14 (s, 2H, CH=N); ms: m/z (%) 884 (M+, 0.1), 799 (0.1), 652
(0.1), 554 (0.1), 480 (0.1), 386 (0.5), 279 (11.9), 167 (27.8), 149
(100). Anal. Calcd for C50H44N8O4S2 (885.09): C, 67.85; H, 5.01;
N, 12.66. Found: C, 68.10; H, 4.90; N, 12.50.
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