Molecules 2019, 24, 973
9 of 12
CuI/Glycerol Method
1-(Azidomethyl)-3- (trifluoromethyl)benzene (0.201 g, 1 mmol) was mixed with 1-ethynyl-3-fluorobenzene
(0.120 g, 1.0 mmol) in glycerol (1 g). CuI (2 mg) was added, and the mixture was stirred for 24 h.
Water (5 mL) was added, and the product
vacuum filtration.
8 appeared as a white precipitate, which was collected using
◦
4
): mp: 72.2–72.7 C; 1H-NMR
1-(2-Trifluoromethylbenzyl)-4-(2-trifluoromethylphenyl)-1H-1,2,3-triazole (
(CDCl3, 400 MHz); 7.98 (d, J = 8 Hz, 1H), 7.74 (m, 3H), 7.64 (t, J = 7 Hz, 1H), 7.55 (t, J = 7 Hz, 1H),
7.48 (q, J = 7 Hz, 2H), 7.18 (d, J = 7 Hz, 1H), 5.83 (s, 2H); 13C-NMR (CDCl3, 100 MHz)
144.9, 133.1,
132.8, 132.0, 131,7, 129.8, 129.3, 128.8, 128.4, 128.2, 127.8, 127.3, 126.3, 126.1, 123.5, 122.3, 50.3; 19F-NMR
59.4; FTIR cm−1: 1340.8, 1102.5, 1085.0, 1058.3,1035.2, 768.9. Anal. Calcd.
δ
δ
(CDCl3, 282 MHz) δ −58.8,
−
for C17H11N3F6 %: C, 54.99; H, 2.99; N, 11.32; F, 30.70. Found: C, 54.71; H, 3.06; N, 11.08; F, 30.73; m/z:
372 ([M + H]+).
Phenyl-[1-(2-trifluoromethylbenzyl)-1H-1,2,3-triazol-4-yl]-methanol (
(CDCl3, 400 MHz) 7.71 (d, 1H), 7.52 (t, 1H), 7.44 (m, 3H), 7.33 (m, 3H),
(s, 1H) δ 141.9, 133.2, 132.8, 130.1, 128.8, 128.6, 128.2, 127.7,
5.69 (s, 2H); 13C-NMR (CDCl3, 300 MHz)
5
): mp: 95.8–96.3 ◦C; 1H-NMR
7.17 (d, 1H), 6.03
δ
δ
δ
δ
δ
δ
,
δ
126.4, 126.3, 126.1, 125.9, 122.4, 121.7, 69.3, 50.2; 19F-NMR (CDCl3, 282 MHz) δ −59.2; FTIR cm−1
:
3212.8, 1449.6, 1312.6, 1120.0, 1036.9, 772.4, 693.9. Anal. Calcd. for C17H14N3F3O %: C, 61.26; H, 4.23;
N, 12.61; F, 17.10. Found: C, 61.24; H, 4.24; N, 12.57; F, 17.05.
1-(3-Fluorobenzyl)-4-phenethyl-1H-1,2,3-triazole (
δ 7.33 (t, 1H) 7.25 (t, 2H), 7.16 (m, 3H), 7.03 (m, 2H),
δ 3.01 (o, 4H); 13C-NMR (CDCl3, 300 MHz)
164.8, 161.5, 141.1, 137.5, 137.4, 130.8, 130.6, 128.6, 128.4,
6
): mp: 77.0–77.4 ◦C; 1H-NMR (CDCl3, 400 MHz)
6.97 (d, 1H), 6.87 (d, 1H) 5.46 (s, 2H),
,
δ
δ
δ
δ
δ
δ
δ
126.1, 123.4, 121.2, 115.7, 115.5, 115.0, 114.6, 53.4, 35.7, 27.5; 19F-NMR (CDCl3, 282 MHz) δ −111.7;
FTIR cm−1: 3108.8, 3059.8, 3024.7, 2932.9, 1590.6, 1450.4, 1245.2, 1054.9, 710.3, 690.0. Anal. Calcd. for
C17H16N3F %: C, 72.58; H, 5.73; N, 14.94; F, 6.75. Found: C, 72.59; H, 5.85; N, 14.97; F, 6.67.
1-(4-Fluorobenzyl)-4-phenethyl-1H-1,2,3-triazole (
7.23 (m, 2H), 7.17 (m, 3H), 7.13 (m, 2H), 7.03 (m, 3H),
(CDCl3, 300 MHz) 164.4, 161.1, 147.9, 141.1, 130.8, 129.8, 128.5, 126.1, 120.8, 116.2, 115.9, 53.0, 35.5,
7
): mp: 96.1–96.3 ◦C; 1H-NMR (CDCl3, 400 MHz)
5.43 (s, 2H),
3.01 (o, 4H); 13C-NMR
δ
δ
δ
δ
δ
δ
δ
27.5; 19F-NMR (CDCl3, 282 MHz) δ −113.1; FTIR cm−1: 3110.4, 3056.9, 2949.8, 2926.2, 2859.4, 1508.7,
1219.7, 1075.4, 776.8, 699.1, 530.4. Anal. Calcd. for C17H16N3F %: C, 72.58; H, 5.73; N, 14.94; F, 6.75.
Found: C, 72.44; H, 5.83; N, 14.81; F, 6.87.
Supplementary Materials: NMR and FTIR spectra of compounds prepared are available in the Supplementary
Material.
Author Contributions: Conceptualization, A.S.; Methodology, A.S.; Validation, M.T, C.H.-C., A.O., K.S., L.T.,
L.G., A.D., B.T., A.S.; Investigation, M.T, C.H.-C., A.O., K.S., L.T., L.G., A.D., B.T., A.S.; Writing—Original Draft
Preparation, A.S.; Writing—Review & Editing, M.T, C.H-C., A.O., K.S., L.T., L.G., A.D., B.T., A.S.; Supervision,
A.S.; Project Administration, A.S.
Funding: This research received no external funding.
Acknowledgments: Authors M.T. and K.S. wish to thank the Undergraduate Research Academy of the University
of Colorado Colorado Springs for summer research support. A.O. acknowledges the award of a Dean’s Scholarship
for 2018. The authors wish to thank Brett Mayer for assistance with obtaining 19F- and 13C-NMR spectra and for
other assistance. The authors wish to thank Christopher Clements, Ashleigh Zeller, Kirstin Knobbe, Wes Robertson,
David Clarke and Sarah Robertson for carrying out preliminary experiments.
Conflicts of Interest: The authors declare no conflict of interest.