Biphenyltetrazole Derivatives of 1,2,4-Triazole
J. Chin. Chem. Soc., Vol. 54, No. 3, 2007 799
Table 4. 13C NMR data of compounds 7a-7o
No.
13C NMR (CDCl3, d, ppm)
7a
7b
7c
7d
7e
170.09, 155.33, 153.90, 151.91, 146.82, 140.85, 138.79, 135.76, 133.00, 131.03, 130.80, 130.61,
130.45, 129.67, 129.26, 129.13, 127.95, 127.23, 122.96, 101.36, 36.51, 12.01
170.12, 153.83, 151.89, 146.77, 140.85, 138.82, 135.83, 135.70, 132.22, 131.42, 131.07, 130.80,
130.63, 129.25, 128.00, 127.50, 127.30, 122.93, 100.98, 36.09, 17.34, 12.07
170.03, 153.94, 151.90, 146.75, 140.85, 139.90, 138.77, 135.72, 132.85, 131.26, 130.99, 130.79,
130.59, 129.38, 129.25, 129.11, 127.90, 127.57, 124.16, 123.00, 101.35, 36.48, 21.23, 11.99
170.03, 155.33, 154.07, 151.94, 146.85, 140.86, 140.74, 138.77, 135.72, 130.99, 130.80, 130.59,
130.32, 129.23, 129.11, 128.61, 127.90, 126.87, 122.99, 101.36, 36.45, 21.30, 11.99
170.08, 155.29, 153.48, 151.84, 146.65, 140.88, 138.77, 135.70, 133.66, 132.71, 132.04, 131.05,
130.77, 130.60, 129.49, 129.23, 128.76, 128.61, 127.93, 127.66, 126.80, 122.91, 122.18, 100.98,
36.41, 11.97
7f
170.27, 155.37, 153.65, 151.81, 146.65, 140.88, 138.77, 135.70, 133.66, 132.71, 132.04, 131.05,
130.77, 130.60, 129.49, 129.23, 128.76, 128.61, 127.93, 127.66, 126.80, 122.91, 122.18, 101.28,
36.61, 11.97
7g
7h
170.26, 155.35, 153.85, 151.87, 146.75, 140.80, 138.85, 136.57, 135.76, 131.49, 131.08, 130.80,
130.64, 129.95, 129.29, 129.14, 128.68, 128.01, 122.90, 101.39, 36.55, 12.01
170.08, 155.29, 153.49, 151.84, 146.65, 140.88, 138.77, 135.70, 133.66, 132.71, 132.04, 131.05,
130.77, 130.60, 129.49, 129.23, 128.76, 128.61, 127.93, 127.66, 126.81, 122.91, 122.18, 100.98,
36.66, 11.99
7i
170.01, 155.40, 153.50, 151.80, 146.65, 140.88, 138.77, 135.70, 133.66, 132.71, 132.04, 131.05,
130.77, 130.60, 129.49, 129.23, 128.76, 128.61, 127.93, 127.66, 126.80, 122.91, 122.18, 100.68,
36.69, 12.02
7j
170.26, 153.79, 151.90, 146.71, 140.82, 138.89, 135.83, 132.96, 132.04, 131.09, 130.80, 130.65,
129.31, 129.20, 128.94, 128.04, 127.86, 124.76, 122.91, 101.42, 36.60, 12.04
169.85, 155.24, 154.48, 153.84, 151.96, 147.32, 140.88, 138.66, 135.73, 132.07, 130.97, 130.85,
130.54, 129.22, 129.05, 128.58, 127.87, 123.04, 121.80, 120.91, 112.34, 101.06, 55.77, 36.57,
11.98
7k
7l
168.59, 160.06, 159.29, 153.17, 151.13, 145.72, 140.28, 139.29, 132.88, 129.72, 128.87, 128.35,
127.45, 127.11, 126.65, 125.82, 125.64, 113.54, 100.25, 54.36, 35.54, 10.84
169.79, 155.30, 153.73, 152.07, 147.38, 140.88, 138.68, 135.76, 131.90, 130.96, 130.85, 130.54,
129.22, 129.05, 128.51, 127.86, 123.07, 121.95, 120.72, 113.13, 101.03, 64.26, 36.63, 14.34, 11.99
170.02, 160.19, 155.65, 154.46, 151.97, 147.03, 140.83, 138.85, 135.63, 130.79, 130.56, 129.22,
129.03, 128.38, 127.84, 125.13, 123.37, 115.14, 101.36, 63.77, 36.34, 14.63, 11.99
169.98, 155.36, 154.11, 151.94, 146.80, 140.85, 139.41, 138.76, 138.39, 135.72, 130.97, 130.80,
130.67, 130.47, 129.25, 129.11, 127.89, 127.74, 124.27, 123.02, 101.38, 36.44, 19.79, 19.67, 12.01
7m
7n
7o
ArH), 2.33 (s, 3H, CH3).
trated under vacuum to afford 4 as a white solid. The solid
was recrystallizd from ethyl acetate/methylene dichloride
to furnish 2.17 g of 4 (91%). mp 166-169 °C (lit.14 163-165
°C); 1H NMR (CDCl3, 400 MHz) d: 7.92 (d, J = 7.0 Hz, 1H,
ArH), 7.50-6.92 (m, 22H, ArH), 2.29 (s, 3H, CH3).
Preparation of 5-(4¢-methylbiphenyl-2-yl)-2-trityltetra-
zole (4)
To a suspension of 3 (5 mmol) in toluene (20 mL) at
room temperature were added 10 mol/L sodium hydroxide
solution (0.50 mL) and triphenylmethyl chloride (5 mmol),
and the resulting mixture was stirred at room temperature
for 3 h. To the reaction mixture was added distilled water (3
mL) and petroleum ether (7 mL), and the resulting slurry
was stirred at 0 °C for 3 h. The slurry was filtered and the
solids were washed with water. The solution was extracted
with methylene dichloride. The organic phase was dried
over anhydrous magnesium sulfate, filtered, and concen-
Preparation of 5-(4¢-bromomethylbiphenyl-2-yl)-2-tri-
tyltetrazole (5)
A solution of 4 (10 mmol), N-bromosuccinimide (10
mmol) and dibenzoyl peroxide (1 mmol) in 60 mL of dry
carbon tetrachloride was refluxed for 8 h, cooled to room
temperature, and then filtered. The filtrate was concen-
trated under reduced pressure to afford the product. Tritura-
tion of the product with diethyl ether furnished 5 as a white