Med Chem Res
FT-IR (KBr): 3120 (C–H str., triazole ring), 3076 (C–H str.,
aromatic ring), 2997 (C–H str., aliphatic), 1753 (C=O str.,
ester), 1639, 1457 (C=C str., aromatic ring), 1209 (C–O
7.47 (s, 1H, C–H triazole) ppm; 13C NMR (100 MHz,
CDCl3): δ = 28.85, 50.84, 67.12, 123.32 (C5 triazole),
126.53, 128.98, 129.02, 129.57, 129.92, 132.99, 134.86,
135.45, 145.66 (C4 triazole), 165.95 (C=O ester) ppm;
HRMS (m/z) calculated for C18H16ClN3O2S [M + H]+:
374.0730 (35Cl), 376.0701 (37Cl). Found: 374.0726 (35Cl),
376.0696 (37Cl).
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asym. str., ester), 1053 (C–O sym. str., ester) cm−1; H
NMR (400 MHz, CDCl3): δ = 4.25 (s, 2H, SCH2), 5.12 (s,
2H, NCH2), 5.20 (s, 2H, OCH2), 7.18–7.36 (m, 10H,
Ar–H), 7.47 (s, 1H, C–H triazole) ppm; 13C NMR (100
MHz, CDCl3): δ = 28.88, 50.93, 68.01, 123.46 (C5 tria-
zole), 126.53, 128.56, 128.77, 128.86, 129.02, 129.61,
134.52, 135.45, 145.65 (C4 triazole), 165.99 (C=O ester)
ppm; HRMS (m/z) calculated for C18H17N3O2S [M + H]+:
340.1075. Found: 340.1070.
4-Methylbenzyl 2-(4-((phenylthio)methyl)-1H-1,2,3-triazol-
1-yl)acetate (5e) White solid; yield: 93%; m.pt: 98–102 °C;
FT-IR (KBr): 3132 (C–H str., triazole ring), 3076 (C–H str.,
aromatic ring), 2991 (C–H str., aliphatic), 1758 (C=O str.,
ester), 1633, 1480 (C=C str., aromatic ring), 1200 (C–O
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4-Methoxybenzyl 2-(4-((phenylthio)methyl)-1H-1,2,3-tria-
zol-1-yl)acetate (5b) White solid; yield: 93%; m.pt:
64–68 °C; FT-IR (KBr): 3120 (C–H str., triazole ring), 3076
(C–H str., aromatic ring), 2952 (C–H str., aliphatic), 1759
(C=O str., ester), 1611, 1480 (C=C str., aromatic ring),
1212 (C–O asym. str., ester), 1054 (C–O sym. str., ester)
asym. str., ester), 1057 (C–O sym. str., ester) cm−1; H
NMR (400 MHz, CDCl3): δ = 2.38 (s, 3H, CH3), 4.27 (s,
2H, SCH2), 5.13 (s, 2H, NCH2), 5.19 (s, 2H, OCH2),
7.21–7.37 (m, 9H, Ar–H), 7.50 (s, 1H, C–H triazole) ppm;
13C NMR (100 MHz, CDCl3): δ = 21.25, 28.84, 50.90,
68.00, 123.41 (C5 triazole), 126.52, 128.72, 129.00, 129.43,
129.64, 131.54, 135.48, 138.80, 145.63 (C4 triazole),
166.03 (C=O ester) ppm; HRMS (m/z) calculated for
C19H19N3O2S [M + H]+: 354.1232. Found: 354.1224.
cm−1 1H NMR (400 MHz, CDCl3): δ = 3.82 (s, 3H,
;
OCH3), 4.25 (s, 2H, SCH2), 5.09 (s, 2H, NCH2), 5.14 (s,
2H, OCH2), 6.89 (d, 2H, Ar–H, J = 8.0Hz), 7.17–7.34 (m,
7H, Ar–H), 7.47 (s, 1H, C–H triazole) ppm; 13C NMR (100
MHz, CDCl3): δ = 28.81, 50.92, 55.33, 67.98, 114.14,
123.41 (C5 triazole), 126.52, 126.64, 129.01, 129.52,
130.38, 135.32, 145.52 (C4 triazole), 160.03, 166.07 (C=O
ester) ppm; HRMS (m/z) calculated for C19H19N3O3S [M +
H]+: 370.1181. Found: 370.1177.
Benzyl 2-(4-(((4-bromophenyl)thio)methyl)-1H-1,2,3-tria-
zol-1-yl)acetate (5f) White solid; yield: 79%; m.pt:
86–90 °C; FT-IR (KBr): 3132 (C–H str., triazole ring), 3076
(C–H str., aromatic ring), 2991 (C–H str., aliphatic), 1750
(C=O str., ester), 1636, 1472 (C=C str., aromatic ring),
1210 (C–O asym. str., ester), 1054 (C–O sym. str., ester)
4-Nitrobenzyl 2-(4-((phenylthio)methyl)-1H-1,2,3-triazol-
1-yl)acetate (5c) White solid; yield: 84%; m.pt: 72–76 °C;
FT-IR (KBr): 3115 (C–H str., triazole ring), 3076 (C–H str.,
aromatic ring), 2958 (C–H str., aliphatic), 1766 (C=O str.,
ester), 1603, 1480 (C=C str., aromatic ring), 1519 (N–O
asym. str., NO2), 1341 (N–O sym. str., NO2), 1219 (C–O
cm−1 1H NMR (400 MHz, CDCl3): δ = 4.21 (s, 2H,
;
SCH2), 5.13 (s, 2H, NCH2), 5.21 (s, 2H, OCH2), 7.18 (d,
2H, Ar–H, J = 8.0 Hz), 7.33–7.37 (m, 7H, Ar–H), 7.49 (s,
1H, C–H triazole) ppm; 13C NMR (100 MHz, CDCl3): δ =
28.82, 50.89, 68.05, 120.57, 123.40 (C5 triazole), 128.56,
128.78, 128.88, 131.23, 132.10, 134.50, 134.55, 145.23 (C4
triazole), 166.01 (C=O ester) ppm; HRMS (m/z) calculated
for C18H16BrN3O2S [M + H]+: 418.0225 (79Br), 420.0204.
(81Br). Found: 418.0220 (79Br), 420.0200 (81Br).
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asym. str., ester), 1057 (C–O sym. str., ester) cm−1; H
NMR (400 MHz, CDCl3): δ = 4.39 (s, 2H, SCH2), 5.17 (s,
2H, NCH2), 5.25 (s, 2H, OCH2), 7.17–7.47 (m, 8H, Ar–H
+C–H triazole), 8.21 (d, 2H, Ar–H, J = 8.0 Hz) ppm; 13C
NMR (100 MHz, CDCl3): δ = 28.63, 50.77, 66.26, 123.45
(C5 triazole), 123.95, 126.65, 128.65, 129.01, 129.61,
135.45, 141.37, 145.73 (C4 triazole), 147.97, 165.71 (C=O
ester) ppm; HRMS (m/z) calculated for C18H16N4O4S [M +
H]+: 385.0926. Found: 385.0920.
4-Methoxybenzyl 2-(4-(((4-bromophenyl)thio)methyl)-1H-
1,2,3-triazol-1-yl)acetate (5g) White solid; yield: 86%; m.
pt: 108–112 °C; FT-IR (KBr): 3137 (C–H str., triazole ring),
3087 (C–H str., aromatic ring), 2935 (C–H str., aliphatic),
1744 (C=O str., ester), 1611, 1475 (C=C str., aromatic
ring), 1222 (C–O asym. str., ester), 1054 (C–O sym. str.,
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4-Chlorobenzyl 2-(4-((phenylthio)methyl)-1H-1,2,3-triazol-
1-yl)acetate (5d) White solid; yield: 93%; m.pt: 94–98 °C;
FT-IR (KBr): 3137 (C–H str., triazole ring), 3087 (C–H str.,
aromatic ring), 2997 (C–H str., aliphatic), 1747 (C=O str.,
ester), 1616, 1469 (C=C str., aromatic ring), 1225 (C–O
ester) cm−1; H NMR (400 MHz, CDCl3): δ = 3.81 (s, 3H,
OCH3), 4.21 (s, 2H, SCH2), 5.10 (s, 2H, NCH2), 5.15 (s,
2H, OCH2), 6.89 (d, 2H, Ar–H, J = 8.0 Hz), 7.18 (d, 2H,
Ar–H, J = 8.0 Hz), 7.27 (d, 2H, Ar–H, J = 8.0 Hz), 7.37 (d,
2H, Ar–H, J = 8.0 Hz), 7.48 (s, 1H, C–H triazole) ppm; 13
C
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asym. str., ester), 1054 (C–O sym. str., ester) cm−1; H
NMR (100 MHz, CDCl3): δ = 29.09, 51.14, 55.46, 68.18,
114.38, 120.80, 123.58 (C5 triazole), 126.81, 130.73,
131.45, 132.28, 134.78, 145.37 (C4 triazole), 160.44,
NMR (400 MHz, CDCl3): δ = 4.24 (s, 2H, SCH2), 5.12 (s,
2H, NCH2), 5.15 (s, 2H, OCH2), 7.18–7.32 (m, 9H, Ar–H),