DOI: 10.1039/C5OB00245A
Organic & Biomolecular Chemistry
ARTICLE
Journal Name
NMR (376 MHz, DMSO-d6) δ -116.21 (s). IR (neat): ν 3116.9 (m), 668.4 (s) cm-1. LC-MS (ESI): 308.1 (M+Na); HRMS (ESI):
1721.4 (s), 1511.9 (m), 1493.3 (s), 1451.0 (s), 1339.7 (m), 1252.7 calculated for C12H11N3O2F3 286.0803, found 286.0795 (M+H, Δ = -
(s), 1202.1 (s), 1089.1 (s), 1051.9 (m), 996.6 (s), 849.9 (s), 828.2 (s), 2.8 ppm).
718.9 (s), 667.6 (s), 639.4 (s) cm-1. LC-MS (ESI): 292.1 (M+Na); Ethyl 1-(4-bromophenyl))-1H-1,2,4-triazole-3-carboxylate, 7f,
HRMS (ESI): calculated for C11H10N3O2ClF 270.0446, found 69%: Mp 152.4-143.8 °C. Compound description: white crystalline
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270.0443 (M+H, Δ = -0.3 ppm).
solid. H NMR (400 MHz, DMSO-d6) δ 9.48 (s, 1H), 7.89 (d, J =
Ethyl 1-(m-tolyl)-1H-1,2,4-triazole-3-carboxylate, 7b, 68%: Mp 8.9 Hz, 2H), 7.82 (d, J = 8.9 Hz, 2H), 4.38 (q, J = 7.1 Hz, 2H), 1.34
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80.2-81.5 °C. Compound description: brown powder. H NMR (400 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) δ 159.6 (C),
MHz, DMSO-d6) δ 9.43 (s, 1H), 7.74 (dt, J = 1.6, 0.8 Hz, 1H), 7.69 155.2 (C), 144.7 (CH), 136.0 (C), 133.2 (2CH), 122.4 (2CH), 121.8
(d, J = 7.8 Hz, 1H), 7.47 (t, J = 7.8 Hz, 1H), 7.29 (d, J = 7.8 Hz, (C), 61.9 (CH2), 14.6 (CH3). IR (neat): 3133.7 (w), 1718.4 (s),
1H), 4.38 (q, J = 7.1 Hz, 2H), 3.36 (s, 1H), 1.34 (t, J = 7.1 Hz, 3H). 1483.9 (s), 1451.2 (s), 1338.4 (m), 1257.5 (s), 1203.3 (s), 1067.0 (s),
13C NMR (101 MHz, DMSO-d6) δ 159.8 (C), 155.0 (C), 144.4 1029.4 (m), 979.8 (s), 826.9 (s), 668.3 (s) cm-1. LC-MS (ESI):
(CH), 140.1 (C), 136.7 (C), 130.1 (CH), 129.7 (CH), 120.8 (CH), 318.0 (M+Na); HRMS (ESI): calculated for C11H11N3O2Br
117.4 (CH), 61.8 (CH2), 21.3 (CH3), 14.6 (CH3). IR (neat): 3109.9 296.0035, found 296.0036 (M+H, Δ = +0.1 ppm).
(w), 1715.6 (s), 1497.7 (m), 1448.3 (s), 1255.8 (s), 1194.4 (s), Ethyl 1-(3-chlorophenyl))-1H-1,2,4-triazole-3-carboxylate, 7g,
1081.8 (s), 1015.9 (s), 886.1 (m), 848.6 (m), 792.5 (s), 669.4 (s) cm- 68%: Mp 114.6-115.5 °C. Compound description: orange powder.
1. LC-MS (ESI): 254.1 (M+Na); HRMS (ESI): calculated for 1H NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 8.06 (t, J = 2.0 Hz,
C12H14N3O2 232.1086, found 232.1084 (M+H, Δ = -0.2 ppm).
1H), 7.90 (ddd, J = 8.1, 2.1, 1.1 Hz, 1H), 7.64 (t, J = 8.1 Hz, 1H),
Ethyl 1-(3-methoxyphenyl))-1H-1,2,4-triazole-3-carboxylate, 7c, 7.57 (ddd, J = 8.1, 2.0, 1.0 Hz, 1H), 4.39 (q, J = 7.1 Hz, 2H), 1.34 (t,
53%: Mp 97.4 °C (decomposed). Compound description: dark J = 7.1 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) δ 159.6 (C),
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brown solid. H NMR (400 MHz, DMSO-d6) δ 9.47 (s, 1H), 7.60 – 155.2 (C), 144.9 (CH), 137.9 (C), 134.6 (C), 132.1 (CH), 128.9
7.38 (m, 3H), 7.06 (ddd, J = 8.0, 2.6, 1.9 Hz, 1H), 4.38 (q, J = 7.1 (CH), 120.3 (CH), 119.1 (CH), 61.9 (CH2), 14.5 (CH3). IR (neat):
Hz, 2H), 3.86 (s, 3H), 1.34 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, 3109.6 (w), 1719.9 (s), 1595.0 (m), 1485.9 (m), 1450.6 (s), 1341.9
DMSO-d6) δ 160.7 (C), 159.7 (C), 155.0 (C), 144.6 (CH), 137.8 (C), (m), 1256.3 (s), 1198.1 (s), 1103.1 (s), 1079.9 (s), 1028.7 (s), 993.6
131.3 (CH), 114.9 (CH), 112.4 (CH), 106.0 (CH), 61.8 (CH2), 56.1 (s), 892.9 (s), 846.7 (m), 792.0 (s), 769.0 (s), 667.4 (s) cm-1. LC-MS
(CH3), 14.6 (CH3). IR (neat): 3106.8 (w), 1730.3 (s), 1607.5 (m), (ESI): 274.0 (M+Na); HRMS (ESI): calculated for C11H11N3O2Cl
1504.9 (s), 1469.9 (s), 1281.3 (s), 1240.8 (s), 1193.7 (s), 1174.4 (s), 252.0540, found 252.0535 (M+H, Δ = -0.5 ppm).
1029.4 (s), 992.2 (s), 882.3 (s), 772.0 (s), 669.4 (s) cm-1. LC-MS Ethyl 1-(4-chlorophenyl))-1H-1,2,4-triazole-3-carboxylate, 7h,
(ESI): 270.1 (M+Na); HRMS (ESI): calculated for C12H14N3O3 67%: Mp 136.5-137.0 °C. Compound description: white crystalline
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248.1035, found 248.1035 (M+H, Δ = 0.0 ppm).
solid. H NMR (400 MHz, DMSO-d6) δ 9.48 (s, 1H), 7.95 (d, J =
Ethyl 1-(3-fluorophenyl))-1H-1,2,4-triazole-3-carboxylate, 7d, 8.9 Hz, 2H), 7.68 (d, J = 8.9 Hz, 2H), 4.38 (q, J = 7.1 Hz, 2H), 1.34
62%: Mp 214.3 °C (decomposed). Compound description: pale tan (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) δ 159.6 (C),
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solid. H NMR (400 MHz, DMSO-d6) δ 9.50 (s, 1H), 7.84 (dt, J = 155.2 (C), 144.7 (CH), 135.6 (C), 133.4 (C), 130.3 (2CH), 122.2
10.0, 2.3 Hz, 1H), 7.79 (ddd, J = 8.0, 2.3, 0.9 Hz, 1H), 7.65 (td, J = (2CH), 61.9 (CH2), 14.6 (CH3). IR (neat): 3125.9 (w), 1725.3 (m),
8.3, 6.2 Hz, 1H), 7.36 (tdd, J = 8.4, 2.6, 0.9 Hz, 1H), 4.39 (q, J = 7.1 1487.3 (s), 1450.4 (s), 1339.4 (m), 1257.5 (s), 1202.6 (s), 1074.8 (s),
Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) 1028.0 (m), 981.5 (s), 831.2 (s), 668.4 (m) cm-1. LC-MS (ESI):
δ 162.8 (d, J = 245.2 Hz, CF), 159.6 (C), 155.2 (C), 144.9 (CH), 274.1 (M+Na); HRMS (ESI): calculated for C11H11N3O2Cl
138.0 (d, J = 10.6 Hz, C), 132.3 (d, J = 9.2 Hz, CH), 116.4 (d, J = 252.0540, found 252.0541 (M+H, Δ = +0.1 ppm). CCDC 1039438.
3.1 Hz, CH), 115.9 (d, J = 21.1 Hz, CH), 108.0 (d, J = 26.8 Hz, CH), Ethyl 7-chloro-5-nitropyrrolo[1,2-c]pyrimidine-3-carboxylate, 12a,
61.9 (CH2), 14.5 (CH3). 19F NMR (376 MHz, DMSO-d6) δ -110.60 72%, Mp 145 °C (decomposition). Compound description: brown
(s). IR (neat): 3102.2 (w), 1719.8 (s), 1606.1 (s), 1496.3 (s), 1449.2 solid. 1H NMR (600 MHz, CDCl3) δ 9.06 (s, 1H), 8.96 (s, 1H), 7.51
(s), 1341.6 (m), 1260.4 (s), 1199.4 (s), 1004.4 (m), 862.5 (s), 783.3 (s, 1H), 4.50 (q, J = 7.2 Hz, 2H), 1.45 (t, J = 7.2 Hz, 3H). 13C NMR
(s), 667.9 (s) cm-1. LC-MS (ESI): 258.1 (M+Na); HRMS (ESI): (151 MHz, CDCl3) δ 163.3 (C), 138.6 (C), 135.5 (CH), 129.0 (C),
calculated for C11H11N3O2F 236.0835, found 236.0835 (M+H, Δ = 127.9 (C), 115.5 (CH), 112.5 (CH), 111.5 (C), 62.6 (CH2), 14.3
0.0 ppm).
(CH3). IR (neat): 3132.5 (w), 1727.3 (s), 1617.9 (w), 1481.0 (s),
1425.5 (m), 1406.5 (m), 1314.6 (s), 1221.6 (s), 1127.7 (s), 1101.3
Ethyl
1-(3-(trifluoromethyl)phenyl))-1H-1,2,4-triazole-3-
carboxylate, 7e, 55%: Mp 129.3-130.4 °C. Compound description: (s), 1010.2 (m), 973.6 (m), 848.4 (m), 783.7 (s), 759.6 (m) cm-1. LC-
orange powder. 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.30 MS (ESI): 270.1.0 (M+H); HRMS (ESI): calculated for
(br s, 1H), 8.28 – 8.20 (m, 1H), 7.92 – 7.80 (m, 2H), 4.40 (q, J = 7.1 C10H9N3O4Cl 270.0282, found 270.0287 (M+H, Δ = 1.9 ppm).
Hz, 2H), 1.35 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, DMSO-d6) CCDC 1039441.
δ 159.6 (C), 155.3 (C), 145.1 (CH), 137.3 (C), 131.8 (CH), 130.94 Ethyl
5-bromo-7-chloropyrrolo[1,2-c]pyrimidine-3-carboxylate,
(q, J = 32.5 Hz, C), 125.7 (q, J = 3.7 Hz, CH), 124.4 (CH), 124.0 (q, 12b, 83%, Mp 109.1-113.0 °C. Compound description: Beige solid.
J = 273.6 Hz, CF3), 117.14 (q, J = 4.0 Hz, CH), 61.9 (CH2), 14.5 1H NMR (400 MHz, CDCl3) δ 8.77 (d, J = 1.6 Hz, 1H), 8.15 (d, J =
(CH3). 19F NMR (376 MHz, DMSO-d6) δ -61.2 (s). IR (neat): 1.6 Hz, 1H), 6.91 (s, 1H), 4.46 (q, J = 7.2 Hz), 1.44 (t, J = 7.2 Hz,
3107.7 (w), 1719.8 (m), 1450.6 (s), 1316.3 (s), 1255.2 (s), 1163.7 3H). 13C NMR (101 MHz, CDCl3) δ 164.4 (C), 134.8 (CH), 131.4
(s), 1116.5 (s), 1081.5 (s), 995.1 (m), 902.9 (m), 807.4 (s), 698.8 (s), (C), 128.7 (C), 117.7 (CH), 115.6 (CH), 110.1 (C), 92.5 (C), 61.9
6 | J. Name., 2012, 00, 1-3
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