N. Nehra, R.K. Tittal, D. Ghule Vikas et al.
Journal of Molecular Structure 1245 (2021) 131013
J = 8.68, 1.97 Hz, 3H, Ar-H), 8.11 (d, J = 7.15 Hz, 1H), 8.32 (s, 1H,
triazole-CH); 13C NMR (125 MHz, DMSO–d6): δ = 19.98, 48.87,
60.92, 66.35, 114.44, 115.27, 122.12, 122.43, 124.96, 125.07, 125.94,
126.45, 128.78, 129.37, 129.72, 134.17, 142.86, 153.56, 155.81,
160.21, 166.79. ESI-MS [M + H]+: m/z cal. for C25H23N4O2S is
443.15, found 443.15.
4H), 7.42 (td, J = 7.71, 7.29, 1.15 Hz, 1H, Ar-H), 7.52 (m, 1H, Ar-H),
8.01 (m, 3H, Ar-H), 8.11 (dd, J = 7.97, 1.09 Hz, 1H,) 8.27 (s, 1H,
triazole-CH); 13C NMR (125 MHz, CDCl3): δ = 19.97, 29.24, 46.49,
61.01, 64.84, 114.43, 115.12, 122.11, 122.38, 124.47, 125.02, 125.57,
126.43, 128.76, 129.36, 129.71, 134.14, 142.81, 153.57, 155.83,
160.75, 166.90. ESI-MS (m/z) C26H24N4O2S: Calculated [M + H]+:
457.17; Experimental: 457.16.
2-(4-(2-(4-((4-chlorophenoxy)methyl)−1H-1,2,3-triazol-1-
yl)ethoxy)phenyl)benzothiazole (4c): Off-white solid, Yield: 85%,
m.p. 130–132 °C. FT-IR (KBr, νmax/cm−1) = 3088, 2941, 2875, 1606,
2-(4-(3-(4-((4-chlorophenoxy)methyl)−1H-1,2,3-triazol-1-yl)
propoxy)phenyl)benzothiazole (4h): Light brown solid, Yield: 83%,
m.p. 120–122 °C. FT-IR (KBr, νmax/cm−1) = 3057, 2960, 2922,
1490, 1240 cm−1
.
1H NMR (500 MHz, DMSO–d6): δ = 4.53 (t,
J = 5.06 Hz, 2H, CH2), 4.85 (t, J = 5.01 Hz, 2H, CH2), 5.18 (s, 2H,
CH2), 7.09 (dd, J = 11.9 and 8.99 Hz, 4H, Ar-H),7.34 (m, 2H, Ar-H),
7.43 (td, J = 7.69,7.28, 1.15 Hz, 1H, Ar-H), 7.53 (ddd, J = 8.29, 7.25,
1.24 Hz, 1H, Ar-H), 8.03 (m, 3H, Ar-H), 8.11 (d, J = 7.50 Hz, 1H, Ar-
H), 8.35 (s, 1H, triazole-CH); 13C NMR (125 MHz, DMSO–d6): δ =
48.92, 61.25, 66.36, 115.27, 116.44, 122.13, 122.45, 124.49, 125.08,
125.20, 125.97, 126.46, 128.80, 129.16, 134.20, 142.39, 153.57,
156.76, 160.21, 166.81. ESI-MS (m/z) C24H20ClN4O2S: Calculated
[M + H]+: 463.10; Experimental: 463.09.
2873, 1604, 1489, 1433, 1236, 1172 cm−1 1H NMR (500 MHz,
.
CDCl3): δ = 2.34 (p, 2H, CH2, J = 6.68 Hz), 4.09 (t, J = 5.97 Hz,
2H, CH2), 4.59 (t, 6.90 Hz, 2H, CH2), 5.16 (s, 2H, CH2),
J
=
6.78 (m, 1H), 7.08 (dd, J = 8.95, 4.33 Hz 4H, Ar-H), 7.20 (m,
1H, Ar-H), 7.33 (m, 1H, Ar-H), 7.43 (m, 1H, Ar-H), 7.53 (m,
1H, Ar-H), 8.03 (m, 2H) 8.11 (d, 1H, Ar-H, J = 7.98 Hz) 8.30
(s, 1H, triazole-CH); 13C NMR (125 MHz, CDCl3): δ = 29.24,
46.52, 61.32, 64.82, 115.09, 116.40, 116.82, 122.09, 122.38, 124.46,
124.67, 124.81, 125.01, 125.58, 126.41, 128.76, 129.01, 129.13,
134.15, 142.33, 153.57, 156.22, 156.77, 160.74, 166.89. ESI-MS
(m/z) C25H22ClN4O2S: Calculated [M + H]+: 477.12; Experimental:
477.11
1-(4-((1-(2-(4-(benzothiazol-2-yl)phenoxy)ethyl)−1H-1,2,3-triazol-
4-yl)methoxy)phenyl) ethan-1-one (4d): Off White solid, Yield: 87%,
m.p. 138–140 °C. FT-IR (KBr, νmax/cm−1) = 3142, 2927, 2875, 1674,
1602, 1508, 1479, 1247, 1178 cm−1
.
1H NMR (500 MHz, DMSO–d6):
1-(4-((1-(3-(4-(benzothiazol-2-yl)phenoxy)propyl)−1H-1,2,3-
triazol-4yl)methoxy)phenyl)ethan-1-one (4i): Light brown solid,
δ = 2.54 (s, 3H, CH3), 4.54 (t, J = 5.05 Hz, 2H, CH2), 4.86 (t,
J = 4.97 Hz, 2H, CH2), 5.28 (s, 2H, CH2), 7.11 (m, 2H),7.16 (m, 2H),
7.44 (m, 1H, Ar-H), 7.53 (ddd, 1H, J = 8.30, 7.18, 1.31 Hz Ar-H), 7.94
(m, 2H), 8.02 (m, 3H, Ar-H), 8.12 (d, J = 7.72 Hz, 1H), 8.41 (s, 1H,
triazole-CH); 13C NMR (125 MHz, DMSO–d6): δ = 26.34, 48.95,
61.21, 66.38, 114.49, 115.30, 122.15, 122.44, 125.10, 125.36, 125.96,
126.47, 128.79, 130.04, 130.37, 134.19, 142.15, 153.57, 160.23, 161.75,
166.80, 196.22. ESI-MS (m/z) C26H23N4O3S: Calculated [M + H]+:
471.15; Experimental: 471.15.
Yield: 85%, m.p. 136–138 °C. FT-IR (KBr, νmax/cm−1
)
=
3055,
1H
2958, 2918, 2850, 1670, 1600, 1483, 1361, 1247, 1180 cm−1
.
NMR (500 MHz, CDCl3): δ = 2.35 (m, 2H, CH2), 2.52 (s, 3H,
CH3), 4.10 (t, 2H, CH2), 4.61 (t, J = 6.30 Hz, 2H, CH2), 5.27 (s,
2H, CH2), 7.08 (d, 2H J = 8.27 Hz), 7.16 (d, 2H, J = 8.28 Hz),
7.44 (t, 1H, Ar-H), 7.53 (t, 1H, Ar-H), 7.94 (d, J = 8,29 Hz, 2H,
Ar-H), 8.02 (d, 3H, Ar-H, J = 8.09 Hz), 8.12 (d, J = 7.74 Hz, 1H,
Ar-H), 8.37 (s, 1H, triazole-CH); 13C NMR (125 MHz, CDCl3):
2-(4-(2-(4-((4-nitrophenoxy)methyl)−1H-1,2,3-triazol-1-yl)
δ
=
26.31, 29.24, 46.56, 61.28, 64.86, 114.45, 115.11, 122.37,
ethoxy)phenyl)benzothiazole (4e): Light brown solid, Yield: 83%,
m.p. 122–124 °C. FT-IR (KBr, νmax/cm−1) = 3078, 2958, 2926,
124.85, 125.02, 125.56, 126.42, 128.76, 130.01, 130.35, 130.52,
134.14, 142.09, 153.57, 160.74, 161.75, 166.90, 196.20. ESI- MS
(m/z) C27H25N4O3S: Calculated [M + H]+: 485.16; Experimental:
485.16.
1606, 1593, 1498, 1255, 1176, 1112 cm−1 1H NMR (500 MHz,
.
DMSO–d6): δ = 4.54 (t, 2H, CH2), 4.87 (t, 2H, CH2), 5.36 (s, 2H,
CH2), 7.03 (d, J = 8.88 Hz,1H), 7.11 (d, J = 8.35 Hz, 2H), 7.28
(d, J = 8.94 Hz, 1H, Ar-H), 7.44 (t, J = 7.30 Hz, 1H, Ar-H), 7.53
(m, J = 7.28 Hz 1H, Ar-H), 8.02 (d, J = 6.93 Hz, 4H), 8.12 (d,
J = 8.18 Hz, 1H), 8.21 (d, J = 8.95 Hz, 1H, Ar-H, 8.45 (s, 1H,
triazole-CH); 13C NMR (125 MHz, DMSO–d6): δ = 48.97, 61.78,
66.36, 115.26, 115.78, 122.12, 122.41, 125.07, 125.56, 125.73, 125.94,
125.98, 126.44, 128.76, 134.17, 140.91, 141.65, 153.54, 160.19, 163.16,
166.77. ESI- MS (m/z) C24H20N5O4S: Calculated [M + H]+: 474.12;
Experimental: 474.12.
2-(4-(3-(4-((4-nitrophenoxy)methyl)−1H-1,2,3-triazol-1-yl)
propoxy)phenyl)benzothiazole (4j): Light brown solid, Yield: 84%,
m.p. 140–142 °C. FT-IR (KBr, νmax/cm−1) = 3080, 2926, 2873,
1606, 1496, 1435, 1342, 1257, 1172, 1112 cm−1 1H NMR (500 MHz,
.
DMSO- d6): δ = 2.35 (m, J = 6.40 Hz, 2H, CH2), 4.10 (t, J = 5.94 Hz,
2H, CH2), 4.61 (t, J = 6.90 Hz, 2H, CH2), 5.34 (s, 2H, CH2), 7.08
(d, J = 8.83 Hz, 2H), 7.27 (d, 2H, J = 9.27 Hz, Ar-H), 7.43 (m, 1H,
Ar-H), 7.52 (m, 1H, Ar-H), 8.02 (d, J = 8.73 Hz, 3H, Ar-H), 8.11 (d,
J = 7.87 Hz 1H, Ar-H), 8.22 (d, J = 9.25 Hz, 2H, Ar-H), 8.36 (s,
1H, triazole-CH); 13CNMR (125 MHz, DMS0-d6): δ = 29.24, 46.61,
61.87, 64.85,115.09,115.22, 122.09, 122.39, 125.02, 125.59, 125.75,
126.42, 128.76, 134.16, 140.93, 141.69, 153.58, 160.73, 163.18,
166.89. ESI-MS (m/z) C25H22N5O4S: Calculated [M + H]+: 488.14;
Experimental: 488.13.
2-(4-(3-(4-(phenoxymethyl)−1H-1,2,3-triazol-1-yl)propoxy)
phenyl)benzothiazole (4f): Light brown solid, Yield: 91%, m.p.
108–110 °C. FT-IR (KBr, νmax/cm−1) = 3064, 3032, 2927, 2870,
1598, 1485, 1268, 1238, 1226, 1170 cm−1 1H NMR (500 MHz,
.
CDCl3): δ = 2.33 (p, 2H, CH2, J = 6.50 Hz), 4.08 (t, J = 6.00 Hz,
2H, CH2), 4.59 (t, J = 6.92 Hz, 2H, CH2), 5.14 (s, 2H, CH2), 6.95 (d,
J = 7.33 Hz,1H), 7.06 (m, 4H, Ar-H) 7.29 (dd, J = 8.69,7.36 Hz, 2H,
Ar-H), 7.42 (m, 1H, Ar-H), 7.52 (m, 1H, Ar-H), 8.01 (dd, J = 8.78,
2.79 Hz, 2H, Ar-H), 8.10 (d, 1H, Ar-H, J = 8.00 Hz), 8.31 (s, 1H,
triazole-CH); 13C NMR (125 MHz, CDCl3): δ = 29.26, 46.50, 60.92,
64.84, 114.56, 115.11, 120.71, 122.10, 122.38, 124.57, 125.01, 125.57,
125.01, 125.57, 126.42, 128.76, 129.40, 134.15, 142.68, 153.58,
157.95, 160.75, 166.91. ESI-MS (m/z) C25H23N4O2S: Calculated:
[M + H]+:443.15; Experimental: 443.15.
2-(4-(4-(4-(phenoxymethyl)−1H-1,2,3-triazol-1-yl)butoxy)
phenyl)benzothiazole (4k): Off White solid, Yield: 92%, m.p. 120–
122 °C. FT-IR (KBr, νmax/cm−1) = 3095, 2954, 2902, 2866, 1606,
1589, 1481, 1257, 1242, 1172 cm−1 1HNMR (500 MHz, DMSO–d6):
.
δ = 1.73 (m, 2H, CH2), 2.00 (m, 2H, CH2), 4.09 (t, J = 6.32 Hz,
2H, CH2), 4.47(t, J = 7.05 Hz, 2H, CH2), 5.14 (s, 2H, CH2), 6.95
(m, 1H, Ar-H), 7.04 (dd, J = 7.79 Hz and 1.01 Hz, 2H, Ar-H), 7.11
(m, 2H, Ar-H), 7.29 (m, 2H, Ar-H), 7.43 (td, 1H, J = 7.70 Hz and
7.29, 1.15 Hz, Ar-H), 7.52 (ddd, J = 8.29 Hz and 7.26 Hz, 1.25 Hz,
1H,Ar-H), 8.03 (m, 2H, Ar-H), 8.11 (m, 1H), 8.27 (s, 1H, triazole-CH).
13CNMR (125 MHz, DMSO–d6): δ = 25.50, 26.39, 49.00, 60.95,
67.05, 114.59, 115.13, 120.73, 122.11, 122.38, 124.36, 125.01, 125.41,
126.43, 128.78, 129.40, 134.15, 142.65, 153.60, 157.97, 160.98,
166.96. ESI- MS (m/z) C26H25N4O2S: Calculated [M + H]+: 457.17;
Experimental: 457.16.
2-(4-(3-(4-((p-tolyloxy)methyl)−1H-1,2,3-triazol-1-yl)propoxy)
phenyl)benzothiazole (4g): Off White solid, Yield: 93%, m.p. 134–
136 °C. FT-IR (KBr, νmax/cm−1) = 3089, 3032, 2958, 2922, 1606,
1512, 1483, 1242, 1176 cm−1
.
1H NMR (500 MHz, CDCl3): δ = 2.22
(s, 3H, CH3), 2.33 (m, 2H, CH2), 4.08 (t, J = 6.01 Hz, 2H, CH2), 4.57
(t, J = 6.92 Hz, 2H, CH2), 5.09(s, 2H, CH2), 6.91 (m, 2H), 7.08 (m,
9