Molecular Diversity
3H, CH-6,5,3), 7.42 (dd, J=6.5, 2.4 Hz, 1H, CH-7), 5.86 (t,
J=2.0 Hz, 1H, CH-4’’), 5.81 (d, J=2.0 Hz, 2H, CH-2’’,6’’),
5.37 (s, 2H, O-CH2-6’), 4.76 (t, J=5.1 Hz, 2H, N-CH2-7’),
4.29 (t, J=5.2 Hz, 2H, O-CH2-8’).
2‑chloro‑N‑(2‑(4‑((quinolin‑8‑yloxy)methyl)‑1H‑1,2,3‑tri-
azol‑1‑yl)ethyl)aniline (11d) Brown solid; Yield: 53%;
Chemical formula: C20H18ClN5O; Mol. wt: 379.84 g/mol;
Rf : 0.24 (EtOAc-Hexane, 80:20); mp: 118–120 °C.
1H NMR (600 MHz, Chloroform-d): δ 8.85 (d, J=4.7 Hz,
1H, CH-2), 8.04 (dd, J= 8.1, 1.7 Hz, 1H, CH-4), 7.70 (s,
1H, CH-5’triazole), 7.41–7.30 (m, 3H, CH-6,5,3), 7.22
(dd, J = 7.2, 1.6 Hz, 1H, CH-7), 7.15 (dd, J = 7.9, 1.5 Hz,
1H, CH-3’’), 7.02 (td, J = 7.8, 1.5 Hz, 1H, CH-5’’), 6.56
(td, J=7.7, 1.4 Hz, 1H, CH-4’’), 6.52 (dd, J=8.2, 1.4 Hz,
1H, CH-6’’), 5.46 (s, 2H, O-CH2-6’), 4.55 (t, J = 6.4 Hz,
1H, NH-9’), 4.45 (t, J = 5.9 Hz, 2H, N-CH2-7’), 3.63 (q,
J=5.9 Hz, 2H, N-CH2-8’).
13C NMR (151 MHz, DMSO-d6): δ 159.57 (Cq-1’’),
159.03 (Cq-3’’,5’’), 153.87 (Cq-8), 148.96 (C-2), 142.63
(Cq-4’ triazole), 139.77 (Cq-8a), 135.75 (C-4), 129.06 (Cq-
4a), 126.70 (C-6), 125.21 (C-5’ triazole), 121.81 (C-3),
120.03 (C-5), 110.15 (C-7), 96.01 (C-4’’), 93.28 (C-2’’,6’’),
65.80 (O-C-8’), 61.90 (O-C-6’), 49.08 (N-C-7’).
HRMS: (ESI+-MS, m/z) calcd for C20H18N4O4
(M+Na)+: 401.1226, found: 401.1229.
8‑((1‑(2‑(naphthalen‑2‑yloxy)ethyl)‑1H‑1,2,3‑tria-
zol‑4‑yl)methoxy)quinoline (10z) Beige solid; Yield:
50%; Chemical formula: C24H20N4O2; Mol. wt: 396.44 g/
mol; Rf : 0.20 (EtOAc-Hexane, 80:20); mp: 123–125 °C.
1H NMR (400 MHz, Chloroform-d): δ 8.92 (s, 1H, CH-
2), 8.12 (s, 1H, CH-4), 7.99 (s, 1H, CH-5’ triazole), 7.73
(d, J=8.1 Hz, 1H, CH-5’’), 7.70–7.64 (m, 2H, CH-4’’,8’’),
7.47–7.29 (m, 6H, CH-7’’,6,5,3,7,6’’), 7.04 (d, J=2.3 Hz,
1H, CH-1’’), 7.01 (dd, J= 8.8, 2.5 Hz, 1H, CH-3’’), 5.58
(s, 2H, OCH2-6’), 4.75 (t, J=5.0 Hz, 2H, NCH2-7’),4.41 (t,
J=4.9 Hz, 2H, OCH2-8’).
13C NMR (151 MHz, Chloroform-d): δ 153.80 (Cq-8),
149.21 (C-2), 144.10 (Cq-4’ triazole), 142.62 (Cq-1’’),
140.26 (Cq-8a), 135.93 (C-4), 129.46 (Cq-4a), 129.42 (C-
3’’), 127.84 (C-5’’), 126.69 (C-6), 124.14 (C-5’ triazole),
121.60 (C-3), 120.22 (C-5), 119.54 (Cq-2’’), 118.11 (C-4’’),
110.91 (C-6’’), 109.93 (C-7), 62.75 (O-C-6’), 49.16 (N-C-
7’), 43.30 (N-C-8’).
HRMS: (ESI+-MS, m/z) calcd for C20H18ClN5O
(M+Na)+: 402.1098, found: 402.1102.
4.2.18 8‑((1‑phenethyl‑1H‑1,2,3‑triazol‑4‑yl)methoxy)
quinoline (14) Brown solid; Yield: 51%; Chemical for-
mula: C20H18N4O; Mol. wt: 330.38 g/mol; Rf : 0.23 (EtOAc-
Hexane, 80:20); mp: 70–72 °C.
13C NMR (101 MHz, Chloroform-d): δ 155.63 (Cq-2’’),
144.24 (Cq-4’ triazole), 135.84 (C-4), 134.25 (Cq-8’’a),
129.68 (C-4’’), 129.27 (Cq-4’’a), 127.64 (C-5’’), 126.81
(C-8’’), 126.57 (C-7’’), 124.50 (C-5’ triazole), 124.07 (C-
6’’), 118.37 (C-3’’), 109.86 (C-7), 106.99 (C-1’’), 66.15
(O-C-8’), 62.83 (O-C-6’), 49.74 (N-C-7’). Not observed
(C-8,2,8a,4a,6,5,3).
1H NMR (600 MHz, Chloroform-d): δ 8.90 (s, 1H, CH-2),
8.11 (d, J=8.2 Hz, 1H, CH-4), 7.48 (s, 1H, CH-5’ triazole),
7.43–7.35 (m, 3H, CH-6,5,3), 7.25 (d, J=6.8 Hz, 1H, CH-7),
7.15–7.09 (m, 3H, CH-11’,13’,12’), 6.99 (dd, J=7.7, 1.7 Hz,
2H, CH-10’,14’), 5.51 (s, 2H, O-CH2-6’), 4.52 (t, J=7.3 Hz,
2H, N-CH2-7’), 3.14 (t, J=7.3 Hz, 2H, Ph-CH2-8’).
13C NMR (151 MHz, Chloroform-d): δ 153.78 (Cq-
8), 149.22 (C-2), 143.86 (Cq-4’ triazole), 140.29 (Cq-8a),
136.83 (Cq-9’), 136.00 (C-4), 129.48 (Cq-4a), 128.70 (C-
11’,13’), 128.56 (C-10’,14’), 127.00 (C-12’), 126.76 (C-6),
123.47 (C-5’ triazole), 121.59 (C-3), 120.15 (C-5), 109.99
(C-7), 62.87 (O-C-6’), 51.66 (N-C-7’), 36.61 (Ph-C-8’).
HRMS: (ESI+-MS, m/z) calcd for C20H18N4O (M+Na)+:
353.1378, found: 353.1384.
HRMS: (ESI+-MS, m/z) calcd for C21H18N4O3
(M+Na)+: 419.1484, found: 419.1494.
N‑(2‑(4‑((quinolin‑8‑yloxy)methyl)‑1H‑1,2,3‑triazol‑1‑yl)
ethyl)aniline (11a) Of-white solid; Yield: 51%; Chemi-
cal formula: C20H19N5O; Mol. wt: 345.40 g/mol; Rf : 0.20
(EtOAc-Hexane, 80:20); mp: 96–98 °C
1H NMR (600 MHz, Chloroform-d): δ 8.93 (s, 1H,
CH-2), 8.15 (s, 1H, CH-4), 7.74 (s, 1H, CH-5’ triazole),
7.49–7.39 (m, 3H, CH-6,5,3), 7.31 (s, 1H, CH-7), 7.13 (dd,
J=8.5, 7.2 Hz, 2H, CH-3’’,5’’), 6.71 (t, J=7.3 Hz, 1H, CH-
4’’), 6.54 (dd, J=8.5, 1.2 Hz, 2H, CH-2’’,6’’), 5.56 (s, 2H,
O-CH2-6’), 4.52 (dd, J=6.5, 4.9 Hz, 2H, N-CH2-7’), 3.65 (t,
J=5.7 Hz, 2H, N-CH2-8’). Not observed (NH-9’).
13C NMR (151 MHz, Chloroform-d): δ 153.82 (Cq-8),
149.24 (C-2), 146.59 (Cq-1’’), 144.15 (Cq-4’ triazole),
140.18 (Cq-8a), 136.08 (C-4), 129.62 (Cq-4a), 129.45 (C-
3’’,5’’), 126.82 (C-6), 124.12 (C-5’ triazole), 121.68 (C-3),
120.26 (C-5), 118.30 (C-4’’), 113.00 (C-2’’,6’’), 110.00 (C-
7), 62.89 (O-C-6’), 49.33 (N-C-7’), 43.66 (N-C-8’).
HRMS: (ESI+-MS, m/z) calcd for C20H19N5O (M+Na)+:
368.1487, found: 368.1486.
4.2.19 2‑(4‑((quinolin‑8‑yloxy)methyl)‑1H‑1,2,3‑tria-
zol‑1‑yl)ethanol (15) Brown solid; Yield: 60%; Chemi-
cal formula: C14H14N4O2; Mol. wt: 270.29 g/mol; Rf : 0.05
(EtOAc-Hexane, 80:20); 0.17 (EtOAc–MeOH, 98:2); mp:
140–142 °C
1H NMR (400 MHz, Chloroform-d): δ 8.82 (dd, J=4.4,
1.7 Hz, 1H, CH-2), 8.11 (dd, J = 8.3, 1.7 Hz, 1H, CH-4),
7.94 (s, 1H, CH-5’ triazole), 7.47–7.35 (m, 3H, CH-6,5,3),
7.27 (dd, J=7.4, 1.6 Hz, 1H, CH-7), 5.44 (s, 2H, O-CH2-6’),
4.45 (dd, J=5.7, 3.9 Hz, 2H, N–CH2-7’), 4.00 (t, J=5.0 Hz,
2H, CH2-8’), Not observed (OH-9’).
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