Molecules 2016, 21, 1635
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9-(2-Chlorobenzyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4m) Yield: 45.2%, m.p. 140–142 ◦C.
1H-NMR (CDCl3, 300 MHz)
: 3.14 (t, 2H, J = 6.00Hz, –CH2–), 4.25 (t, 2H, J = 6.00 Hz, –CH2–), 5.23 (s,
δ
2H, –OCH2–), 7.04 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz, Ar-H), 7.22 (s, 1H, Ar-H), 7.27–7.33 (m, 2H, Ar-H),
7.40–7.43 (m, 1H, Ar-H), 7.57–7.40 (m, 1H, Ar-H), 7.83 (d, 1H, J = 3.00 Hz, Ar-H), 8.20 (s, 1H, –N=CH–).
13C-NMR (CDCl3, 75 MHz)
δ: 27.37, 41.64, 67.26, 109.44, 117.88, 124.64, 125.49, 126.80, 128.66, 128.97,
129.26, 132.58, 134.14, 141.99, 150.23, 157.97. IR (KBr, cm−1): 1517, 1213, 1047. ESI-HRMS calculated for
C17H15ClN3O+ ([M + H]+): 312.0898; found: 312.0903.
9-(3-Chlorobenzyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4n) Yield: 33.2%, m.p. 127–128 ◦C.
1H-NMR (CDCl3, 300 MHz)
δ: 3.14 (t, 2H, J = 6.00 Hz, –CH2–), 4.24 (t, 2H, J = 6.00 Hz, –CH2–), 5.11 (s,
2H, –OCH2–), 7.02 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz, Ar-H), 7.22 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz,
Ar-H), 7.31 (m, 3H, Ar-H), 7.45 (s, 1H, Ar-H), 7.77 (d, 1H, J = 3.00 Hz, Ar-H), 8.19 (s, 1H, –N=CH–).
13C-NMR (CDCl3, 75 MHz)
δ: 27.38, 41.66, 69.17, 109.11, 118.16, 124.66, 125.26, 125.49, 127.23, 128.03,
129.32, 129.78, 134.38, 138.51, 142.04, 150.23, 157.89. IR (KBr, cm−1): 1512, 1211, 1012. ESI-HRMS
calculated for C17H15ClN3O+ ([M + H]+): 312.0898; found: 312.0894.
9-(4-Chlorobenzyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4o) Yield: 51.3%, m.p. 166–168 ◦C.
1H-NMR (CDCl3, 300 MHz)
δ
: 3.13 (t, 2H, J = 6.00 Hz, –CH2–), 4.23 (t, 2H, J = 6.00 Hz, –CH2–), 5.10 (s,
2H, –OCH2–), 7.00 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz, Ar-H), 7.22 (d, 1H, J = 9.00 Hz, Ar-H), 7.33–7.40
(m, 3H, Ar-H), 7.76 (d, 1H, J = 3.00 Hz, Ar-H), 8.19 (s, 1H, –N=CH–). 13C-NMR (CDCl3, 75 MHz)
δ:
27.35, 41.64, 69.23, 109.15, 118.13, 124.62, 125.42, 128.62, 128.65, 133.65, 134.94, 142.02, 150.24, 157.90. IR
(KBr, cm−1): 1522, 1212, 1016. ESI-HRMS calculated for C17H15ClN3O+ ([M + H]+): 312.0898; found:
312.0893.
9-[(2,4-Dichlorobenzyl)oxy]-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4p) Yield: 51.6%, m.p. 128–130 ◦C
1H-NMR (CDCl3, 300 MHz)
: 3.15 (t, 2H, J = 6.00 Hz, –CH2–), 4.25 (t, 2H, J = 6.00 Hz, –CH2–), 5.18
.
δ
(s, 2H, –OCH2–), 7.03 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz, Ar-H), 7.23–7.30 (m, 2H, Ar-H), 7.44 (d, 1H,
J = 3.00 Hz, Ar-H), 7.52 (d, 1H, J = 3.00 Hz, Ar-H), 7.81 (d, 1H, J = 3.00 Hz, Ar-H), 8.21 (s, 1H, –N=CH–).
13C-NMR (CDCl3, 75 MHz)
δ: 27.40, 41.66, 66.69, 109.37, 117.88, 124.72, 125.69, 127.14, 129.10, 129.35,
129.46, 132.87, 133.15, 134.07, 142.04, 150.20, 157.73. IR (KBr, cm−1): 1520, 1223, 1012. ESI-HRMS
calculated for C17H15Cl2N3O+ ([M + H]+): 346.0508; found: 346.0515.
9-[(2,6-Dichlorobenzyl)oxy]-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4q
1H-NMR (CDCl3, 300 MHz)
: 3.15 (t, 2H, J = 6.00 Hz, –CH2–), 4.25 (t, 2H, J = 6.00 Hz, –CH2–), 5.35
(s, 2H, –OCH2–), 7.04 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz, Ar-H), 7.22–7.39 (m, 4H, Ar-H), 7.88 (d, 1H,
) .
Yield: 59.8%, m.p. 168–170 ◦C
δ
J = 3.00 Hz, Ar-H), 8.20 (s, 1H, –N=CH–). 13C-NMR (CDCl3, 75 MHz)
δ: 27.47, 42.72, 66.46, 109.28,
118.50, 124.64, 125.64, 129.39, 129.31, 130.47, 131.73, 136.92, 142.05, 150.38, 159.40. IR (KBr, cm−1): 1520,
1219, 1010. ESI-HRMS calculated for C17H15Cl2N3O+ ([M + H]+): 346.0508; found: 346.0506.
9-(3-(Trifluoromethyl)benzyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4r) Yield: 47.7%, m.p.
◦
1
116–118 C. H-NMR (CDCl3, 300 MHz) δ: 3.15 (t, 2H, J = 6.00 Hz, –CH2–), 4.25 (t, 2H, J = 6.00 Hz,
–CH2–), 5.19 (s, 2H, –OCH2–),7.04 (dd, 1H, J1 = 6.00 Hz, J2 = 3.00 Hz, Ar-H), 7.26 (q, 1H, Ar-H), 7.50–7.65
(m, 3H, Ar-H), 7.73 (s, 1H, Ar-H), 7.80 (d, 1H, J = 3.00 Hz, Ar-H), 8.21 (s, 1H, –N=CH–). 13C-NMR
(CDCl3, 75 MHz) δ: 27.41, 41.68, 69.26, 109.14, 118.17, 123.89, 123.92, 124.72, 124.75, 125.63, 129.00,
129.38, 130.52, 137.52, 142.06, 150.28, 157.90. IR (KBr, cm−1): 1518, 1210, 1016. ESI-HRMS calculated for
C18H15F3N3O+ ([M + H]+): 346.1162; found: 346.1165.
9-(4-Methlybenzyloxy)-5,6-dihydro-[1,2,4]triazolo[3,4-a]isoquinoline (4s) Yield: 61.3%, m.p. 163–164 ◦C.
1H-NMR (CDCl3, 300 MHz)
δ: 2.36 (s, 3H, –CH3), 3.12 (t, 2H, J = 6.00 Hz, –CH2–), 4.23 (t, 2H,
J = 6.00 Hz, –CH2–), 5.09 (s, 2H, –OCH2–), 7.01 (dd, 1H, J1 = 9.00 Hz, J2 = 3.00 Hz, Ar-H), 7.20 (d,
3H, J = 9.00 Hz, Ar-H), 7.34 (d, 2H, J = 6.00 Hz, Ar-H), 7.79 (d, 1H, J = 3.00 Hz, Ar-H), 8.18 (s, 1H,
–N=CH–). 13C-NMR (CDCl3, 75 MHz)
δ: 21.14, 27.44, 41.73, 70.10, 109.27, 118.30, 124.62, 125.17, 127.59,
129.22, 133.43, 137.79, 142.03, 150.40, 158.34. IR (KBr, cm−1): 1517, 1211, 1022. ESI-HRMS calculated for
C18H18N3O+ ([M + H]+): 292.1444; found: 292.1445.