S. Mohammed et al. / Tetrahedron 68 (2012) 8156e8162
8161
[Mþ1]þ, 275 [MþNa]þ; HRMS (ESIþ): m/z 275.0908 calcd for
C14H12N4OþNaþ (275.0903).
7.92e7.87 (m, 3H), 7.81 (s, 1H), 7.58e7.51 (m, 2H), 2.92e2.90 (m,
1H), 2.16 (m, 2H), 1.88 (m, 2H), 1.79 (m, 1H), 1.55e1.39 (m, 4H),
1.36e1.22 (m, 1H); 13C NMR (CDCl3, 125 MHz):
d 154.5, 134.8, 133.3,
4.5.6. 1-Thiophen-3-yl-4-phenyl-1H-1,2,3-triazole (1f). Yield: 95%;
white solid; mp 164e166 ꢀC; Rf (20% EtOAc: n-hexane) 0.43; 1H NMR
132.7, 129.9, 128.2, 127.9, 127.3, 126.8, 119.0, 118.1, 117.7, 35.4, 33.0,
29.7, 26.2, 26.1; IR (neat):nmax 3130, 2925, 1569, 1499, 1240,
1040 cmꢁ1; ESI-MS: m/z 278 [M]þ; HRMS (ESIþ): m/z 300.1468
calcd for C18H19N3þNaþ (300.1471).
(CDCl3, 400 MHz):
7.62e7.61 (q, J¼1.2, 3.2 Hz,1H), 7.53e7.52 (m,1H), 7.50e7.48 (m,1H),
d
8.11 (s, 1H), 7.92 (d, J¼1.6 Hz, 1H), 7.90 (s, 1H),
7.68 (m, 1H), 7.44 (m, 1H), 7.38e7.32 (m, 1H); 13C NMR (CDCl3,
100 MHz):
d
148.0,135.9,130.2, 128.9,128.5, 127.3, 125.9,120.9, 118.0,
4.5.13. 1-(4-Phenoxy-phenyl)-4-phenyl-1H-1,2,3-triazole
114.1; IR (neat):nmax 3103, 1558, 1447, 1231, 1074 cmꢁ1; ESI-MS: m/z
228 [Mþ1]þ, 250 [MþNa]þ; HRMS (ESIþ): m/z 250.0415 calcd for
C12H9N3SþNaþ (250.0409).
(1m). Yield: 80%; white solid; mp 171e173 ꢀC; Rf (30% EtOAc: n-
hexane) 0.73; 1H NMR (CDCl3, 500 MHz):
d 8.15 (s, 1H), 7.92 (d,
J¼8.3 Hz, 2H), 7.74 (d, J¼8.9 Hz, 2H), 7.44 (t, J¼7.7 Hz, 2H), 7.34 (m,
3H), 7.16 (m, 3H), 7.08 (d, J¼8.5 Hz, 2H); 13C NMR (CDCl3, 100 MHz):
4.5.7. 1-(4-Methoxyphenyl)-4-hexyl-1H-1,2,3-triazole (1g). Yield:
92%; light yellow solid; mp 90e93 ꢀC; Rf (30% EtOAc: n-hexane)
d 158.0, 156.4, 148.4, 132.3, 130.0, 128.9, 128.4, 125.9, 124.2, 122.3,
119.5, 119.3, 117.8; IR (neat):nmax 3128, 2921, 2359, 1587, 1514, 1244,
1110 cmꢁ1; ESI-MS: m/z 314 [Mþ1]þ; HRMS (ESIþ): m/z 314.1261
calcd for C20H15N3OþHþ (314.1288).
0.35; 1H NMR (CDCl3, 400 MHz):
d
7.61 (d, J¼5.6 Hz, 2H), 7.60 (s,
1H), 6.99 (d, J¼6.8 Hz, 2H), 3.89 (s, 3H), 2.78 (t, J¼7.6 Hz, 2H), 1.73
(m, 2H), 1.43e1.30 (m, 6H), 0.91 (t, J¼6.0 Hz, 3H); 13C NMR (CDCl3,
100 MHz):
d
159.6, 149.0, 130.8, 122.1, 119.0, 114.7, 55.6, 31.6, 29.4,
4.5.14. 1-(4-Methoxyphenyl)-4-cyclohexyl-1H-1,2,3-triazole
29.0, 25.7, 22.6, 14.1; IR (neat):nmax 3130, 3080, 2926, 2359, 1520,
1254, 1038 cmꢁ1; ESI-MS: m/z 260 [Mþ1]þ, 280 [MþNa]þ; HRMS
(ESIþ): m/z 260.1738 calcd for C15H21N3OþHþ (260.1757).
(1n). Yield: 94%; white solid; mp 90e93 ꢀC; Rf (30% EtOAc: n-
hexane) 0.35; 1H NMR (CDCl3, 500 MHz):
d 7.62 (m, 3H), 6.98 (d,
J¼6.8 Hz, 2H), 3.82 (s, 3H), 2.82 (m, 1H), 2.18 (m, 2H), 1.90e1.80 (m,
3H), 1.40 (m, 4H), 1.30e1.26 (m, 1H); 13C NMR (CDCl3, 125 MHz):
4.5.8. 1-(4-Methoxyphenyl)-4-octyl-1H-1,2,3-triazole
94%; light yellow solid; mp 53e55 ꢀC; Rf (20% EtOAc: n-hexane) 0.36;
1H NMR (CDCl3, 400 MHz):
7.71e7.61 (m, 3H), 7.03 (d, J¼6.8 Hz,
(1h). Yield:
d 159.6, 154.2, 132.5, 121.8, 117.2, 114.7, 50.0, 38.8, 33.1, 29.4, 26.2; IR
(neat):nmax 3127, 2926, 2359, 1724, 1518, 1256, 1044 cmꢁ1; ESI-MS:
m/z 258 [Mþ1]þ; HRMS (ESIþ): m/z 258.1614 calcd for
C15H19N3OþHþ (258.1601).
d
2H), 3.89 (s, 3H), 2.82 (t, J¼7.6 Hz, 2H), 1.72 (m, 2H), 1.43e1.27 (m,
10H), 0.94 (t, J¼6.4 Hz, 3H); 13C NMR (CDCl3, 100 MHz):
d 159, 149.0,
132.5, 122.4, 119.0, 114.7, 55.6, 31.9, 30.4, 29.7, 29.5, 29.4, 25.7, 22.7,
4.5.15. 1-(Indol-5-yl)-4-cyclohexyl-1H-1,2,3-triazole
85%; light pink solid; mp 136e139 ꢀC; Rf (30% EtOAc: n-hexane)
0.31; 1H NMR (CDCl3, 400 MHz):
8.48 (s,1H), 7.91 (d, J¼1.6 Hz,1H),
(1o). Yield:
14.1; IR (neat):nmax 3125, 2921, 2359, 1727, 1520, 1254, 1046 cmꢁ1
;
ESI-MS: m/z 288 [Mþ1]þ, 310 [MþNa]þ; HRMS (ESIþ): m/z 288.2079
d
calcd for C17H25N3OþHþ(288.2070).
7.68 (s, 1H), 7.56e7.47 (m, 2H), 7.33 (t, J¼2.8 Hz, 1H), 6.63 (t,
J¼2.4 Hz, 1H); 13C NMR (CDCl3, 125 MHz):
d 154.0, 135.4, 130.9,
4.5.9. 1-(4-Hydroxyphenyl)-4-octyl-1H-1,2,3-triazole
97%; light pink solid; mp 98e100 ꢀC; Rf (30% EtOAc: n-hexane)
0.29; 1H NMR (CDCl3, 400 MHz):
(1i). Yield:
128.0, 126.2, 118.5, 113.2, 111.8, 103.3, 35.4, 33.1, 26.2, 26.1; IR
(neat):nmax 3350, 2925, 2359, 1447, 1221, 1044 cmꢁ1; ESI-MS: m/z
267 [Mþ1]þ; HRMS (ESIþ): m/z 267.1632 calcd for C16H18N4þHþ
(267.1604).
d
7.64 (s, 1H), 7.58 (d, J¼6.8 Hz,
2H), 7.06 (d, J¼7.2 Hz, 2H), 2.79 (t, J¼7.6 Hz, 2H), 1.76e1.72 (m, 2H),
1.39e1.26 (m, 10H), 0.88 (t, J¼6.8 Hz, 3H); 13C NMR (CDCl3,
100 MHz):
d 157.8, 148.8, 129.9, 122.3, 119.5, 116.7, 31.9, 29.4, 29.3,
Acknowledgements
29.2, 29.2, 25.5, 22.7, 14.1; IR (neat):nmax 3119, 2919, 1599, 1237,
1059 cmꢁ1; ESI-MS: m/z 274 [Mþ1]þ, 296 [MþNa]þ; HRMS (ESIþ):
m/z 296.1739 calcd for C16H23N3OþNaþ (296.1733).
M.S., A.K.P. and B.A.D. thank CSIR for award of Senior Research
Fellowship. Authors are thankful to analytical department, IIIM for
NMR and MS analysis of our compounds.
4.5.10. 1-(4-Hydroxyphenyl)-4-cyclohexyl-1H-1,2,3-triazole
(1j). Yield: 98%; white solid; mp 167e169 ꢀC; Rf (30% EtOAc: n-
Appendix A. Supplementary data
hexane) 0.31; 1H NMR (CDCl3, 400 MHz):
d 7.60e7.56 (m, 3H), 7.03
(d, J¼8.8 Hz, 2H), 6.25 (brs, OH), 2.86 (m, 1H), 2.14 (m, 2H), 1.85 (m,
Spectra of catalyst and all new compounds. Supplementary data
associated with this article can be found, in the online version at
2H), 1.76 (m, 1H), 1.50e1.38 (m, 3H), 1.35e1.23 (m, 2H); 13C NMR
(CDCl3, 100 MHz): d 157.4, 154.0, 130.0, 122.2, 118.1, 116.6, 35.2, 33.0,
26.1, 26.0; IR (neat):nmax 3139, 2926, 2359, 1600, 1519, 1223,
1061 cmꢁ1; ESI-MS: m/z 244 [Mþ1]þ, 266 [MþNa]þ; HRMS (ESIþ):
m/z 244.1466 calcd for C14H17N3OþHþ (244.1444).
References and notes
4.5.11. 1-Phenyl-4-(4-fluoroanilinomethyl)-1H-1,2,3-triazole
(1k). Yield: 96%; white solid; mp 94e96 ꢀC; Rf (60% EtOAc: n-
1. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40,
2004e2021.
2. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed.
2002, 41, 2596e2599.
3. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057e3064.
4. Kawamoto, S. A.; Coleska, A.; Ran, X.; Yi, H.; Yang, C.-Y.; Wang, S. J. Med. Chem.
2012, 55, 1137e1146.
hexane) 0.31; 1H NMR (CDCl3, 400 MHz):
d 7.92 (s, 1H), 7.67 (d,
J¼7.2 Hz, 2H), 7.41 (t, J¼7.6 Hz, 2H), 7.18 (t, J¼7.6 Hz, 1H), 7.12 (d,
J¼7.6 Hz, 2H), 7.06 (d, J¼7.6 Hz, 2H), 4.91 (d, J¼5.6 Hz, 2H); 13C NMR
(CDCl3, 100 MHz):
d 158.0, 156.3, 148.3, 132.2, 130.1, 124.2, 122.4,
5. Wilkinson, B. L.; Bornaghi, L. F.; Houston, T. A.; Innocenti, A.; Vullo, D.; Supuran,
C. T.; Poulsen, S.-A. J. Med. Chem. 2007, 50, 1651e1657.
6. Pagliai, F.; Pirali, T.; Grosso, E. D.; Brisco, R. D.; Tron, G. C.; Sorba, G.; Genazzani,
A. A. J. Med. Chem. 2006, 49, 467e470.
7. Lee, T.; Cho, M.; Ko, S.-Y.; Youn, H.-J.; Baek, D. J.; Cho, W.-J.; Kang, C.-Y.; Kim, S.
J. Med. Chem. 2007, 50, 585e589.
8. Piotrowska, D. G.; Balzarini, J.; G1owacka, I. E. Eur. J. Med. Chem. 2012, 47,
501e509.
9. Speers, A. E.; Adam, G. C.; Cravatt, B. F. J. Am. Chem. Soc. 2003, 125, 4686e4687.
120.2, 119.8, 119.3, 56.6; IR (neat):nmax 3350, 3120, 2930, 1588, 1513,
1241, 1042 cmꢁ1; ESI-MS: m/z 268 [M]þ; HRMS (ESIþ): m/z
268.1175 calcd for C15H13FN4þHþ (268.1197).
4.5.12. 1-(Naphth-2-yl)-4-cyclohexyl-1H-1,2,3-triazole (1l). Yield:
80%; white solid; mp 139e141 ꢀC; Rf (20% EtOAc: n-hexane) 0.50;
1H NMR (CDCl3, 500 MHz):
d
8.15 (s, 1H), 8.00 (d, J¼8.8 Hz, 1H),