P. S. Phatak, B. P. Sathe, S. T. Dhumal, N. N. M. A. Rehman,
P. P. Dixit, V. M. Khedkar, and K. P. Haval
Vol 000
1
1670, 1599, 1251, 1174, 844, 823; H-NMR (300 MHz,
CDCl3 + DMSO-d6): δ 2.54 (s, 3H, -CH3), 3.77 (s, 3H,
-OMe), 5.28 (d, 4H, -CH2), 6.84 (d, J = 9 Hz, 2H, Ar-H),
7.09 (d, J = 9 Hz, 2H, Ar-H), 7.51 (d, J = 9 Hz, 2H, Ar-H),
7.93 (d, J = 9 Hz, 2H, Ar-H), 8.14 (s, 1H, 1,2,3-triazole-
H), 10.23 (s, 1H, -NH); 13C-NMR (75 MHz, DMSO-d6): δ
26.0, 35.8, 54.8, 61.9, 113.4, 114.0, 120.6, 125.4, 130.0,
(75 MHz, CDCl3 + DMSO-d6): δ 25.8, 52.2, 61.2, 113.9,
116.0, 117.2, 119.2, 123.5, 124.7, 129.4, 129.9, 133.6,
138.8, 142.4, 161.5, 163.3, 195.9.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(3-
methoxyphenyl)acetamide (8k). Yield: 81%; M.P.: 160°C;
brown solid; IR (Neat) ν cmÀ1: 3261, 3077, 1670, 1598,
1551, 1491, 1362, 1261, 1233, 1165, 1043, 1033, 852,
1
833; H-NMR (300 MHz, CDCl3 + DMSO-d6): δ 2.55 (s,
131.0, 142.0, 155.5, 161.6, 161.8, 162.9, 195.7.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(2-
3H, -CH3), 3.77 (s, 3H, -OMe), 5.28 (s, 4H, -CH2), 6.65
(dd, J = 3 Hz & 9 Hz, 1H, Ar-H), 7.04–7.08 (m, 3H,
Ar-H), 7.20 (t, J = 9 Hz, 1H, Ar-H), 7.34 (t, J = 2 Hz,
1H, Ar-H), 7.93 (d, J = 9 Hz, 2H, Ar-H), 8.02 (s, 1H,
1,2,3-triazole-H), 10.18 (s, 1H, -NH); 13C-NMR
(75 MHz, CDCl3 + DMSO-d6): δ 25.8, 52.4, 54.7, 61.3,
105.1, 107.2, 109.6, 111.5, 113.9, 124.5, 129.0, 130.0,
chlorophenyl)acetamide (8g).
Yield: 76%; M.P.: 200°C;
white solid; IR (Neat) ν cmÀ1: 3338, 2993, 1697, 1668,
1600, 1532, 1443, 1254, 1181, 1167, 1047, 842, 754;
1H-NMR (300 MHz, CDCl3 + DMSO-d6): δ 2.55 (s, 3H,
-CH3), 5.29 (s, 2H, -CH2), 5.45 (s, 2H, -CH2), 7.08 (d,
J = 6 Hz, 2H, Ar-H), 7.14 (t, J = 6 Hz, 1H, Ar-H), 7.27
(t, J = 6 Hz, 1H, Ar-H), 7.42 (d, J = 9 Hz, 1H, Ar-H),
7.90 (d, J = 9 Hz, 1H, Ar-H), 7.94 (d, J = 9 Hz, 2H,
Ar-H), 8.12 (s, 1H, 1,2,3-triazole-H), 9.78 (s, 1H, -NH);
13C-NMR (75 MHz, DMSO-d6): δ 25.9, 52.6, 61.2,
114.0, 112.8, 124.5, 125.3, 125.7, 126.8, 129.0, 130.0,
138.6, 142.6, 159.4, 161.5, 163.0, 196.1.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-o-
tolylacetamide (8l). Yield: 82%; M.P.: 200°C; white solid;
IR (Neat) ν cmÀ1: 3287, 3096, 2920, 1670, 1600, 1537,
1249, 1229, 1173, 1045, 961, 834, 815; 1H-NMR
(400 MHz, CDCl3): δ 2.25 (s, 3H, -CH3), 2.55 (s, 3H,
-CH3), 5.28 (s, 2H, -CH2), 5.35 (s, 2H, -CH2), 7.06 (d,
J = 8 Hz, 2H, Ar-H), 7.12–7.20 (m, 2H, Ar-H),
7.51–7.59 (m, 2H, Ar-H), 7.93 (d, J = 8 Hz, 2H, Ar-H),
8.05 (s, 1H, 1,2,3-triazole-H), 9.48 (s, 1H, -NH);
13C-NMR (75 MHz, CDCl3 + DMSO-d6): δ 17.4, 25.8,
133.7, 142.1, 154.4, 161.6, 164.0, 195.7.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-
fluorophenyl)acetamide (8h).
Yield: 82%; M.P.: 245°C;
white solid; IR (Neat) ν cmÀ1: 3329, 1689, 1665, 1660,
1
1560, 1509, 1252, 1215, 1178, 1047, 840, 812; H-NMR
(300 MHz, CDCl3 + DMSO-d6): δ 2.56 (s, 3H, -CH3),
5.28 (s, 4H, -CH2), 7.00 (t, J = 9 Hz, 2H, Ar-H), 7.07 (d,
J = 9 Hz, 2H, Ar-H), 7.55–7.59 (m, 2H, Ar-H), 7.94 (d,
J = 9 Hz, 2H, Ar-H), 8.03 (s, 1H, 1,2,3-triazole-H), 10.29
(s, 1H, -NH); 13C-NMR (75 MHz, CDCl3 + DMSO-d6):
δ 25.9, 52.2, 61.3, 113.9, 114.7, 115.0, 120.9, 121.0,
124.7, 130.0, 133.7, 142.4, 161.6, 163.0, 196.0.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(2-
methoxyphenyl)acetamide (8i). Yield: 84%; M.P.: 150°C;
52.1, 61.2, 113.9, 124.0, 124.6, 125.3, 125.7, 129.9,
130.0, 130.8, 134.5, 142.4, 148.8, 161.5, 163.3, 195.9.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(4-
nitrophenyl)acetamide (8m).
Yield: 75%; M.P.: 260°C;
brown solid; IR (Neat) ν cmÀ1: 3299, 1700, 1661,
1599, 1573, 1495, 1345, 1251, 1175, 1047, 855, 843,
1
821; H-NMR (300 MHz, CDCl3 + DMSO-d6): δ 2.56
(s, 3H, -CH3), 5.30 (s, 2H, -CH2), 5.39 (s, 2H, -CH2),
7.09 (d, J = 9 Hz, 2H, Ar-H), 7.84 (d, J = 9 Hz, 2H,
Ar-H), 7.94 (d, J = 9 Hz, 2H, Ar-H), 8.11 (s, 1H,
1,2,3-triazole-H), 8.19 (d, J = 9 Hz, 2H, Ar-H), 10.93
(s, 1H, -NH); 13C-NMR (75 MHz, CDCl3 + DMSO-d6):
δ 25.8, 52.3, 61.3, 113.9, 118.8, 124.2, 124.6, 129.9,
142.8, 143.6, 157.2, 161.8, 163.8, 185.1, 196.0; HRMS
(ESI)+ calcd for C19H17N5O5 [M + H]+: 396.1263 and
white solid; IR (Neat) ν cmÀ1: 3326, 2916, 1693, 1667,
1597, 1536, 1460, 1251, 1224, 1170, 1045, 1034, 839,
745; 1H-NMR (300 MHz, CDCl3 + DMSO-d6): δ 2.55 (s,
3H, -CH3), 3.87 (s, 3H, -OMe), 5.28 (s, 2H, -CH2), 5.39
(s, 2H, -CH2), 6.91 (t, J = 6 Hz, 2H, Ar-H), 7.05 (d,
J = 9 Hz, 2H, Ar-H), 7.08–7.11 (m, 1H, Ar-H), 7.93 (d,
J = 9 Hz, 2H, Ar-H), 8.04 (s, 1H, 1,2,3-triazole-H), 8.13
(d, J = 9 Hz, 1H, Ar-H), 9.12 (s, 1H, -NH); 13C-NMR
(75 MHz, CDCl3 + DMSO-d6): δ 25.8, 52.6, 55.2, 61.3,
110.0, 113.9, 120.2, 120.4, 124.4, 124.6, 126.0, 130.0,
found 396.1308.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-1-
moropholinoethanone (8n).
Yield: 76%; M.P.: 255°C;
brown solid; IR (Neat) ν cmÀ1: 3329, 3156, 2982, 2916,
2850, 1673, 1661, 1643, 1600, 1421, 1257, 1235, 1177,
1111, 1056, 1042, 848, 820; 1H-NMR (400 MHz,
CDCl3): δ 2.56 (s, 3H, -CH3), 3.56–3.73 (m, 8H,
4x-CH2 of morpholine), 5.24 (s, 2H, -CH2), 5.30 (s, 2H,
-CH2), 7.04 (d, J = 8 Hz, 2H, Ar-H), 7.85 (s, 1H, 1,2,3-
triazole-H), 7.94 (d, J = 8 Hz, 2H, Ar-H); 13C-NMR
(100 MHz, CDCl3): δ 26.6, 42.8, 46.0, 51.0, 62.2, 66.5,
66.8, 114.7, 124.8, 130.8, 162.2, 163.5, 196.9; HRMS
(ESI)+ calcd for C17H20N4O4 [M + H]+: 345.1518 and
found 345.1564.
142.7, 148.3, 161.5, 162.9, 196.1.
2-(4-((4-Acetylphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-(3-
chlorophenyl)acetamide (8j).
Yield: 78%; M.P.: 250°C;
grey solid; IR (Neat) ν cmÀ1: 3327, 3158, 2917, 2848,
1692, 1666, 1597, 1543, 1429, 1251, 1182, 1050, 1037,
1
843, 783; H-NMR (300 MHz, CDCl3 + DMSO-d6): δ
2.56 (s, 3H, -CH3), 5.28 (s, 2H, -CH2), 5.29 (s, 2H,
-CH2), 7.07 (d, J = 9 Hz, 2H, Ar-H), 7.24 (t, J = 6 Hz,
1H, Ar-H), 7.42–7.50 (m, 2H, Ar-H), 7.75 (t, J = 2 Hz,
1H, Ar-H), 7.94 (d, J = 9 Hz, 2H, Ar-H), 8.01 (s, 1H,
1,2,3-triazole-H), 10.36 (s, 1H, -NH); 13C-NMR
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet