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7.76–7.84 (m, 2H, Qui-H), 7.72 (s, 1H, Trz-H), 7.28–7.61 (m, 2H,
Qui-H), 5.83 (s, 2H, Qui-CH2), 4.79 (d, J = 1.2 Hz, 2H, Trz-CH2). 13C
NMR (CDCl3, 75 MHz) dC 154.4 (1C, Qui-C), 148.5 (1C, Trz-C),
147.6 (1C, Qui-C), 137.7 (1C, Qui-C), 130.2 (1C, Qui-C), 127.2–
129.1 (4C, Qui-C), 122.3 (1C, Trz-C), 119.6 (1C, Qui-C), 56.52 (1C,
Qui-CH2), 56.3 (1C, Trz-CH2). HR-EIMS: calcd for C13H12N4O
[M+1], 240.2606, found: 240.2605. Anal. Calcd for C13H12N4O: C,
64.99; H, 5.03; N, 23.32. Found: C, 64.45; H, 5.47; N, 23.66.
pyranose, 13 (2.47 mmol, 0.81 g) in 1:1 ratio of THF/H2O, afforded
compound, 21. Oily liquid (0.86 g, 72%); Rf = 0.20 (1:9 MeOH–
CHCl3); 1H NMR (CDCl3, 300 MHz) : dH 7.72–7.79 (m, 2H, Qui-H),
7.59 (s, 1H, Trz-H), 7.57–7.49 (m, 2H, Qui-H), 7.36–7.26 (m, 2H,
Qui-H), 5.46 (s, 2H, Qui-CH2), 5.22–4.77 (m, 4H, Sacc-H), 4.67 (d,
J = 7.8 Hz, 1H ano-H), 4.23–3.35 (m, 5H, Sacc-H), 2.04 (s, 3H, Ace-
H), 1.989 (s, 3H, Ace-CH3), 1.32 (d, J = 5.1 Hz, 3H, Ethy-CH3). 13C
NMR (CDCl3, 75 MHz): dC 170–169.5 (2C, Ace-C@O), 153.9 (1C,
Qui-C), 145.1 (1C, Trz-C), 142.8–128.4 (3C, Qui-C), 125 (1C, Trz-
C), 124.1–116.7 (5C, Qui-C), 99.8 (1C, Ano-C), 92.1 (1C, Ace-C),
71.8–66.9 (5C, Sacc-C), 49.3 (1C, Trz-CH2), 29.9 (1C, Qui-CH2),
20.7–20.6 (2C, Ace-CH3), 20.1 (1C, Ethy-CH3). Anal. Calcd for
6.4.1. 2-((4-Phenyl-1H-1,2,3-triazol-1-yl)methyl)quinoline (18)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.45 g) and
phenyl acetylene, 10 (2.47 mmol, 0.27 g) in 1:1 ratio of THF/H2O,
afforded compound, 18. White solid (0.61 g, 87%); mp 160–162 °C;
Rf = 0.35 (1:9 MeOH–CHCl3); 1H NMR (CDCl3, 300 MHz): dH 8.08–
8.18 (m, 2H, Qui-H), 7.93 (s, 1H, Trz-H), 7.74–7.83 (m, 2H, Qui-H),
7.56–7.61 (m, 2H, Qui-H), 7.32–7.43 (m, 5H, Phe-H), 5.89 (s, 2H,
Qui-CH2). 13C NMR (CDCl3, 75 MHz) dC 154.6 (1C, Qui-C), 148.3
(1C, Trz-C), 147.6 (1C, Qui-C), 137.7 (1C, Qui-C), 130.4 (1C, Qui-C),
130.19 (1C, Qui-C), 128.7–129.1 (3C, Qui-C), 127.1–128.1 (5C, Phe-
C), 125.7 (1C, Trz-C), 120.2 (1C, Phe-C), 119.6 (1C, Qui-C), 56.4 (1C,
Qui-CH2). HR-EIMS: calcd for C18H14N4 [M+1], 286.3306, found:
286.3354. Anal. Calcd for C18H14N4: C, 75.50; H, 4.93; N, 19.57.
Found: C, 75.94; H, 4.58; N, 19.13.
C25H28N4O8 (512.51): C, 58.59; H, 5.51; N, 10.93. Found: C, 58.91;
H, 5.29; N, 10.56.
6.4.5. 2-((4-((2,3-Di-O-acetyl-4,6-O-butylidene-b-D-glucopyrano
syloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-quinoline (22)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.453 g)
and
2-propyn-1-yl-2,3-di-O-acetyl-4,6-O-butylidene-b-D-gluco-
pyranose, 14 (2.47 mmol, 0.87 g) in 1:1 ratio of THF : H2O, afforded
compound, 22. Oily liquid (0.96 g, 69%); Rf = 0.23 (1:9 MeOH–
CHCl3); 1H NMR (CDCl3, 300 MHz) : dH 8.06–8.19 (m, 2H, Qui-H),
7.74–7.84 (m, 2H, Qui-H), 7.7 (s, 1H, Trz-H), 7.3–7.61 (m, 2H,
Qui-H), 5.83 (s, 2H, Qui-CH2), 4.77–5.16 (m, 4H, Sacc-H), 4.66 (d,
J = 7.8 Hz, 1H ano-H), 3.37–4.49 (m, 5H, Sacc-H), 2.02 (s, 3H, Ace-
H), 1.83 (s, 3H, Ace-H), 1.55–1.62 (m, 2H, Buty-CH2), 1.32–1.4 (m,
2H, Buty-CH2), 0.86–0.91 (m, 3H, Buty-CH3). 13C NMR (CDCl3) dC
169.9–169.5 (2C, Ace-C@O), 154.3 (1C, Qui-C), 147.6 (1C, Trz-C),
144.6 (1C, Qui-C), 137.8 (1C, Qui-C), 130.2 (1C, Qui-C), 127.2–
129.1 (4C, Qui-C), 123.3 (1C, Trz-C), 119.7 (1C, Qui-C), 102.5 (1C,
Ano-C), 100.1 (1C, Ace-C), 72.1–66.5 (5C, Sacc-C), 62.8 (1C, Trz-
CH2), 56.3 (1C, Qui-CH2), 35.9 (1C, Buty-CH2), 20.5–20.7 (2C, Ace-
CH3), 17.3 (1C, Buty-CH3), 13.8 (1C, Buty-CH2). Anal. Calcd for
6.4.2. 2-((4-((2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyloxy)
methyl)-1H-1,2,3-triazol-1-yl)methyl)-quinoline (19)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.45 g)
and 2-propyn-1-yl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside, 11
(2.47 mmol, 0.95 g) in 1:1 ratio of THF/H2O, afforded compound,
19. Oily liquid (0.96 g, 68%); Rf = 0.23 (1:9 MeOH–CHCl3); 1H
NMR (CDCl3, 300 MHz) : dH 8.06–8.19 (m, 2H, Qui-H), 7.74–7.84
(m, 2H, Qui-H), 7.73 (s, 1H, Trz-H), 7.30–7.61 (m, 2H, Qui-H),
5.84 (s, 2H, Qui-CH2), 4.81–5.20 (m, 4H, Sacc-H), 4.66 (d,
J = 7.8 Hz, 1H ano-H), 4.08–4.27 (m, 4H, Sacc-H), 1.97–2.06 (m,
12H, Ace-H). 13C NMR (CDCl3) dC 169.2–170.6 (4C, Ace-C@O),
154.4 (1C, Qui-C), 147.7 (1C, Trz-C), 144.9 (1C, Qui-C), 137.7 (1C,
Qui-C), 130.2 (1C, Qui-C), 127.2–129.2 (4C, Qui-C), 123.4 (1C, Trz-
C), 119.6 (1C, Qui-C), 99.6 (1C, Ano-C), 68.2–72.0 (3C, Sacc-C),
62.8 (1C, Trz-CH2), 60.4–61.8 (2C, Sacc-C), 56.3 (1C, Qui-CH2),
20.4–21.0 (4C, Ace-CH3). HR-EIMS: calcd for C27H30N4O10 [M+1],
C27H32N4O8 (540.56): C, 59.99; H, 5.97; N, 10.36. Found: C, 59.58;
H, 5.54; N, 10.87.
6.4.6. 2-((4-((2,3,4,6-Tetra-O-acetyl-a-D-mannopyranosyl
oxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-quinoline (23)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.453 g)
and 2-propyn-1-yl-2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside,
570.5479, found: 570.5467. Anal. Calcd for C27H30N4O10
56.84; H, 5.30; N, 9.82. Found: C, 56.43; H, 5.47; N, 9.66.
:
C,
15 (2.47 mmol, 0.95 g) in 1:1 ratio of THF/H2O, afforded compound,
23. Oily liquid (0.87 g, 62%); Rf = 0.27 (1:9 MeOH–CHCl3); 1H NMR
(CDCl3, 300 MHz) : dH 8.08–8.21 (m, 2H, Qui-H), 7.77–7.85 (m, 1H,
Qui-H), 7.76 (s, 1H, Trz-H), 7.73–7.74 (s, 1H, Qui-H), 7.55–7.61 (m,
1H, Qui-H), 7.32–7.35 (m, 1H, Qui-H), 5.86 (s, 2H, Qui-CH2), 5.21–
5.30 (m, 2H, Sacc-H), 4.95 (d, J = 1.6 Hz, 1H ano-H), 4.66–4.86 (m,
2H, Sacc-H), 4.25–4.31 (m, 2H, Sacc-H), 4.05–4.15 (m, 2H, Sacc-
H), 1.97–2.13 (m, 12H, Ace-H). 13C NMR (CDCl3) dC 169.7–170.7
(4C, Ace-C@O), 154.2 (1C, Qui-C), 144 (1C, Trz-C), 137.9 (1C, Qui-
C), 130.2 (1C, Qui-C), 127.2–129.2 (5C, Qui-C), 123.7 (1C, Trz-C),
119.7 (1C, Qui-C), 96.9 (1C, Ano-C), 66.2–69.4 (4C, Sacc-C), 62.3
(1C, Trz-CH2), 61.0 (1C, Sacc-C), 56.3 (1C, Qui-CH2), 20.6–20.8
(4C, Ace-CH3). Anal. Calcd for C27H30N4O10 (570.55): C, 56.84; H,
5.30; N, 9.82. Found: C, 56.43; H, 5.71; N, 9.56.
6.4.3. 2-((4-((2,3,4,6-Tetra-O-acetyl-b-
methyl)-1H-1,2,3-triazol-1-yl)methyl)-quinoline (20)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.453 g)
and 2-propyn-1-yl-2,3,4,6-tetra-O-acetyl-b- -galactopyranoside,
D-galactopyranosyloxy)
D
12 (2.47 mmol, 0.95 g) in 1:1 ratio of THF/H2O, afforded compound,
20. Oily liquid (0.78 g, 55%); Rf = 0.26 (1:9 MeOH–CHCl3); 1H NMR
(CDCl3, 300 MHz) dH 8.06–8.20 (m, 2H, Qui-H), 7.73–7.84 (m, 2H,
Qui-H), 7.76 (s, 1H, Trz-H), 7.28–7.61 (m, 2H, Qui-H), 5.84 (s, 2H,
Qui-CH2), 5.16–5.38 (m, 2H, Sacc-H), 4.81–5.01 (m, 2H, Sacc-H),
4.63 (d, J = 7.8 Hz, 1H ano-H), 3.9–4.14 (m, 4H, Sacc-H), 1.84–2.13
(m, 12H, Ace-H). 13C NMR (CDCl3) dC 169.4–170.4 (4C, Ace-C@O),
154.3 (1C, Qui-C), 147.6 (1C, Trz-C), 144.7 (1C, Qui-C), 137.8 (1C,
Qui-C), 130.2 (1C, Qui-C), 127.2–129.1 (4C, Qui-C), 123.4 (1C, Trz-
C), 119.7 (1C, Qui-C), 100.2 (1C, Ano-C), 67–70.8 (3C, Sacc-C),
62.7 (1C, Trz-CH2), 61.2 (1C, Sacc-C), 56.3 (1C, Qui-CH2), 41 (1C,
Sacc-C), 20.5–20.6 (4C, Ace-CH3). HR-EIMS: calcd for C27H30N4O10
6.4.7. 2-((4-((2,3,4-Tri-O-acetyl-b-D-ribopyranosyloxy)methyl)-
1H-1,2,3-triazol-1-yl)methyl)-quinoline (24)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.453 g)
and
2-propyn-1-yl-2,3,4,-tri-O-acetyl-b-
D
-ribopyranoside,
16
[M+1], 570.5479, found: 570.5493. Anal. Calcd for C27H30N4O10
C, 56.84; H, 5.30; N, 9.82. Found: C, 56.24; H, 5.52; N, 9.54.
:
(2.47 mmol, 0.77 g) in 1:1 ratio of THF/H2O, afforded compound,
24. Oily liquid (0.72 g, 58%); Rf = 0.21 (1:9 MeOH–CHCl3); 1H
NMR (CDCl3, 300 MHz): dH 8.06–8.18 (m, 2H, Qui-H), 7.8–7.83
(m, 1H, Qui-H), 7.78 (s, 1H, Trz-H), 7.29–7.75 (m, 3H, Qui-H),
5.84 (s, 2H, Qui-CH2), 5.23–5.46 (m, 2H, Sacc-H), 4.84–5.14 (m,
2H, Sacc-H), 4.66 (d, J = 13.8 Hz, 1H ano-H), 4.35–4.31 (m, 2H,
Sacc-H), 3.81–4.29 (m, 1H, Sacc-H), 2.01–2.11 (m, 9H, Ace-H). 13C
6.4.4. 2-((4-((2,3-Di-O-acetyl-4,6-O-ethylidene-b-
syloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-quinoline (21)
A mixture of 2-azidomethyl quinoline, 8 (2.47 mmol, 0.453 g)
and 2-propyn-1-yl-2,3-di-O-acetyl-4,6-O-ethylidene-b- -gluco-
D-glucopyrano
D