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LETTER
O2 (1 atm) at 110 °C for 6 h. The reaction mixture was
(18) Claus, P.; Doppler, T.; Gakis, N.; Georgarakis, M.;
Giezendanner, H.; Gilgen, P.; Heimgartner, H.; Jackson, B.;
Märky, M.; Narasimhan, N. S.; Rosenkranz, H. J.; Wunderli,
A.; Hansen, H.-J.; Schmid, H. Pure Appl. Chem. 1973, 33,
339.
allowed to cool, diluted with EtOAc (200 mL) and washed
successively with 1 M HCl aq solution (30 mL) and brine (30
mL) three times. The organic phase was separated, dried,
and concentrated in vacuo. Purification by flash column
chromatography (Si, 50 g, 0–10% EtOAc–cyclohexane, 60
min) gave 5-phenyl-2-(p-tolyl)-2H-tetrazole 5f (1.51 g,
93%) as a white solid; mp 103–104 °C. IR: 1507, 1448,
1212, 1012 cm–1. 1H NMR (400 MHz, CDCl3): δ = 8.26 (dd,
J = 2.0, 8.1 Hz, 2 H), 8.08 (d, J = 8.6 Hz, 2 H), 7.57–7.47 (m,
3 H), 7.38 (d, J = 8.6 Hz, 2 H), 2.46 (s, 3 H) ppm. 13C NMR
(101 MHz, CDCl3): δ = 165.1, 139.9, 134.8, 130.5, 130.2,
128.9, 127.3, 127.0, 120.0, 119.8, 77.3, 77.2, 77.0, 76.7, 21.2
ppm. HRMS (ESI+): m/z calcd for C14H13N4: 237.1135;
found: 237.1128.
(19) Li, Y.; Gao, L.-X.; Han, F.-S. Chem. Commun. 2012, 48,
2719.
(20) (a) Henderson, R. K.; Jiménez-González, C.; Constable, D.
J. C.; Alston, S. R.; Inglis, G. G.; Fisher, G.; Sherwood, J.;
Binks, S. P.; Curzons, A. D. Green Chem. 2011, 13, 854.
(b) Pace, V.; Hoyos, P.; Castoldi, L.; Domínguez de María,
P.; Alcántara, A. R. ChemSusChem 2012, 5, 1369.
(c) Yilgor, E.; Ekin Atilla, G.; Ekin, A.; Kurt, P.; Yilgor, I.
Polymer 2003, 44, 7787.
(21) Meier, H.; Heinzelmann, W.; Heimgartner, H. Helv. Chim.
Acta 1985, 68, 1283.
(22) Abu Thaher, B.; Zahra, J.; El-Abadelah, M. M.; Voelter, W.
Z. Naturforsch., B: J. Chem. Sci. 2004, 59, 930.
(23) Böhm, V. P. W.; Herrmann, W. A. Angew. Chem. Int. Ed.
2000, 39, 4036.
Representative Example for the Preparation of 2,4,5-
Trisubstituted 1,2,3-Triazoles: 4,5-Diphenyl-2-(p-tolyl)-
2H-1,2,3-triazole (9f)
A solution of 5-phenyl-2-(p-tolyl)-2H-tetrazole 5f (200 mg,
0.85 mmol) in 2-PrOH–2-MeTHF (1:1, 10 mL) was stirred
under irradiation with a UVB lamp (270–330 nm) for 19 h.
The reaction mixture was concentrated in vacuo and the
residue purified by reverse-phase chromatography (Si C18,
50–95% MeCN–H2O, HCO2H modifier, 30 min) to give 4,5-
diphenyl-2-(p-tolyl)-2H-1,2,3-triazole 9f (62 mg, 47%) as a
brown gum. IR: 1510, 1441, 1268 cm–1. 1H NMR (400 MHz,
CDCl3): δ = 8.10 (d, J = 8.6 Hz, 2 H), 7.72–7.65 (m, 4 H),
7.43 (dd, J = 1.9, 4.9 Hz, 6 H), 7.33 (d, J = 8.6 Hz, 2 H), 2.45
(s, 3 H). 13C NMR (101 MHz, CDCl3): δ = 145.7, 137.6,
137.3, 130.9, 129.8, 128.6, 128.6, 128.5, 127.1, 118.7, 21.1.
HRMS (ESI+): m/z calcd for C21H18N3: 312.1495; found:
312.1496.
(24) Molteni, G.; Orlandi, M.; Broggini, G. J. Chem. Soc., Perkin
Trans. 1 2000, 3742.
(25) Wentrup, C.; Benedikt, J. J. Org. Chem. 1980, 45, 1407.
(26) Wentrup, C.; Damerius, A.; Reichen, W. J. Org. Chem.
1978, 43, 2037.
(27) Patel, H.; Vyas, K.; Pandey, S.; Fernandes, P. Tetrahedron
1996, 52, 661.
(28) Representative Example for the Preparation of 2,5-
Diaryl Tetrazoles: 5-Phenyl-2-(p-tolyl)-2H-tetrazole (5f)
A solution of p-tolyl boronic acid (1.86 g, 13.7 mmol), 5-
phenyl tetrazole (1.00 g, 6.84 mmol), and Cu2O (5 mol%,
0.049 g, 0.342 mmol) in DMSO (30 mL) was stirred under
Synlett 2014, 25, 2480–2484
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