JOURNAL OF CHEMICAL RESEARCH 2015 189
1H NMR: δ 7.96 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.60 (d, J=8.5 Hz,
1H), 7.54–7.52 (m, 1H),7.46–7.43 (m, 1H), 7.42–7.29 (m, 2H), 5.39 (s,
2H), 3.67 (s, 3H); 13C NMR: δ 166.9, 141.1, 140.3, 136.4, 134.4, 132.0,
131.8, 130.4, 129.7, 128.7, 128.5, 127.9, 124.1, 121.1, 52.5, 51.1; LRMS
(EI, 70 eV) m/z (%): 327 (M+ +2, 21), 325 (M+, 17), 310 (25), 290 (–Cl,
24), 231 (46), 156 (58), 116 (100); HRMS (EI) for C17H12ClN3O2(M+):
calcd 325.0634, found 325.0611.
(35), 115(100); HRMS (EI) for C16H13N3(M+): calcd 247.1134, found
247.1131.
5‑Methyl‑3‑p‑tolyl‑8H‑[1,2,3]triazolo[5,1‑a]isoindole (2k): Brown
1
solid; yield 86%; m.p. 185.5–187.1 °C. H NMR: δ 7.69 (t, J=8.5 Hz,
3H), 7.17 (d, J=8.0 Hz, 2H), 7.04 (s, 2H), 5.57 (s, 2H), 2.33 (s, 3H),
2.28 (s, 3H); 13C NMR: δ 147.8, 140.6, 137.7, 133.3, 130.9, 129.9, 129.3,
128.8, 127.5, 125.4, 125.3, 123.0, 119.3, 53.3, 21.1, 20.6; LRMS (EI,
70 eV) m/z (%): 263 (M+ +2, 21), 261 (M+, 32), 231 (23), 203 (25), 129
(100); HRMS (EI) for C17H15N3(M+): calcd 261.1325, found 261.1321.
5‑Methyl‑3‑(4‑nitrophenyl)‑8H‑[1,2,3]triazolo[5,1‑a]isoindole
(2l): Yellow solid; 74% yield; m.p. 191.2–192.4 °C. 1H NMR: δ
8.23 (d, J=8.0 Hz, 2H), 7.97 (t, J=8.0 Hz, 2H), 7.46 (s, 1H), 7.20
(d, d, J=7.5 Hz, 1H), 7.14 (d, d, J=7.5 Hz, 1H), 5.69 (s, 2H), 2.34 (s,
3H); 13C NMR: δ 147.1, 145.6, 141.2, 136.7, 133.7, 130.5, 129.1, 126.0,
124.1, 123.5, 121.2, 53.8; LRMS (EI, 70 eV) m/z (%): 294 (M+ +2, 11),
292 (M+, 34), 277(18), 246 (24), 155 (32), 127 (100); HRMS (EI) for
C16H12N4O2(M+): calcd 292.1034, found 292.1031.
3‑(4‑Nitrophenyl)‑8H‑[1,2,3]triazolo[5,1‑a]isoindole (2e):13 Light
yellow solid; 58% yield; m.p. 163.5–164.9 °C (lit.13 162–164 °C)
(uncorrected). 1H NMR: δ 8.51 (d, J=6.0 Hz, 2H), 8.00 (d, J=8.0 Hz,
1H), 7.89 (t, J=8.0 Hz, 1H), 7.82 (d, J=8.5 Hz, 2H), 7.57–7.54 (m,
2H), 5.55 (s, 2H); 13C NMR: δ 144.5, 142.8, 141.6, 138.1, 134.3, 133.3,
130.9, 129.9, 128.8, 126.5, 125.4, 53.3; LRMS (EI, 70 eV) m/z (%): 280
(M+ +2, 17), 278(M+, 34), 232 (31), 188 (57), 128 (100).
3‑(4‑Methylphenyl)‑8H‑[1,2,3]triazolo[5,1‑a]isoindole (2f):12,13
White solid; yield 85%; m.p. 160.4–161.7 °C (lit.12,13 160–162 °C)
1
(uncorrected) H NMR: δ 7.97 (d, J=8.0 Hz, 1H), 7.90 (d, J=9.0 Hz,
2H), 7.83 (d, J=8.0 Hz, 1H), 7.71–7.67 (m, 1H), 7.54–7.44 (m, 1H), 7.36
(d, J=9.0 Hz, 2H), 5.51 (s, 2H), 2.40 (s, 3H); 13C NMR: δ 144.8, 140.6,
140.2, 139.7, 131.3, 130.9, 130.4, 130.1, 129.3, 128.8, 126.5, 122.4, 52.3,
22.1; LRMS (EI, 70 eV) m/z (%): 249 (M+ +2, 11), 247 (M+, 56), 232
(23), 219 (100).
The authors thank the Major Project in Institutions of Higher
Education of Hunan Province (No. 14A133), Hunan Provincial
Natural Science Foundation (No. 14JJ7076), and Scientific and
Technological Innovative team of Shaoyang University (2012)
for financial support.
3‑(5‑Methylthiophen‑2‑yl)‑8H‑[1,2,3]triazolo[5,1‑a]isoindole (2g):
Yellow solid; 66% yield; m.p. 183.1–184.7 °C (uncorrected) 1H NMR: δ
7.52 (d, J=8.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.43–7.39 (m, 3H), 6.82
(s, 2H), 5.35 (s, 2H); 13C NMR: δ 147.8, 140.6, 137.7, 133.3, 131.0, 130.0,
129.2, 128.8, 127.5, 125.4, 125.3, 123.0, 119.3, 53.3; LRMS (EI, 70 eV)
m/z (%): 255 (M+ +2, 11), 253 (M+, 26), 238 (52), 177 (32), 156 (100);
HRMS (EI) for C14H11N3S(M+): calcd 253.0734, found 253.0728.
3‑Octyl‑8H‑[1,2,3]triazolo[5,1‑a]isoindole (2h):12 Pale yellow solid;
yield 76%; m.p. 79.8–81.7 °C (lit.12 79–80°C) (uncorrected) 1H NMR:
δ 7.61 (d, J=7.5 Hz, 1H), 7.51–7.45 (m, 2H), 7.38 (t, J=7.5 Hz,
1H), 5.30 (s, 2H), 2.94 (t, J=7.5 Hz, 2H), 1.82–1.77 (m, 2H), 1.42 (t,
J=4.0 Hz, 2H), 1.39 (d, J=7.0 Hz, 2H), 1.34–1.25 (m, 6H), 0.87 (t,
J=7.0 Hz, 3H); 13C NMR: δ 140.6, 139.4, 139.3, 128.7, 128.5, 127.7,
124.1, 120.8, 50.9, 31.8, 29.6, 29.5, 29.3, 29.2, 29.1, 22.6, 14.1; LRMS
(EI, 70 eV) m/z (%): 271 (M+ +2, 24), 269(M+, 33), 254 (12), 198 (31),
179 (46), 132 (100).
Received 8 February 2015; accepted 25 February 2015
Paper 1503194 doi: 10.3184/174751915X14255507995495
Published online: 18 March 2015
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8H‑[1,2,3]Triazolo[5,1‑a]isoindole (2i):3 Black solid; yield 74%; m.p.
1
83.8–85.4 °C (lit.14 84–86°C) (uncorrected) H NMR: δ 7.84 (s, 1H),
7.66 (d, J=7.5 Hz, 1H), 7.54 (t, J=7.5 Hz, 1H), 7.48 (t, J=7.5 Hz, 1H),
7.42 (t, J=7.5 Hz, 1H), 5.35 (s, 2H); 13C NMR: δ 141.9, 140.2, 128.9,
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5‑Methyl‑3‑phenyl‑8H‑[1,2,3]triazolo[5,1‑a]isoindole (2j): Brown
solid; yield 83%; m.p. 180.5–181.6 °C. H NMR: δ 7.84 (d, J=8.0 Hz,
2H), 7.78 (s, 1H), 7.42 (t, J=7.5 Hz, 2H), 7.33 (t, J=7.5 Hz, 2H), 7.12
(s, 2H), 5.66 (s, 2H), 2.34 (s, 3H); 13C NMR: δ 147.9, 140.8, 133.5,
130.9, 130.4, 130.1, 128.9, 128.7, 128.0, 125.6, 123.2, 119.7, 53.5, 20.7;
LRMS (EI, 70 eV) m/z (%): 249 (M+ +2, 18), 247(M+, 23), 232 (23), 155
1
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