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Journal Name
ARTICLE
o
temperature at 0 C. Extracted with CH2Cl2, washed with 10% (1
H-benzo[d][1,2,3]triazol-1-yl)(3-(trifluoromethyl)
Na2CO3, water, and brine solution, the organic layer wasdried phenyl)methanone (2f). White crystalline solid, 0.817g, yield
over anhydrous Na2SO4, concentrated till dry under reduced 53%; Rf = 0.7 (10% ethyl acetate/n-hexanDe)O;I:m10.p.1.0=3592/C-56R3A°1C4;13I1RE
-1
max(cm ) 3230, 2920, 1699, 1594, 1485, 1452, 1390,
pressure. Further, purification using flash column (KBr):
ν
1
chromatography using gradient mixtures of ethyl acetate and
n-
1330, 1302, 1265, 1071, 958, 946, 802, 759, 749, 693, 677; H
NMR (300 MHz, CDCl3): δ 8.48 (s, 1H), 8.42 (d, = 7.5Hz,
1H), 8.35 (d, = 8.1Hz, 1H), 8.15 (d, = 8.4, 1H), 7.92 (d,
7.5Hz, 1H), 7.74-7.68 (m, 2H), 7.55 (t,
(2a).17 NMR (75 MHz, CDCl3): δ 165.2, 145.7, 134.8, 132.2, 132.0
White crystalline Solid, 1.73g, yield 95%; Rf = 0.6 (10% ethyl 130.6, 130.0, 129.9, 129.0, 128.5, 128.4, 126.5, 120.2 and
hexane afforded product 2a-q in pure.
J
J
J
J
13
=
Physical data of developed compounds (2a-q)
J
= 7.5Hz, 1H);
C
(1H-1,2,3-Benzotriazole-1-yl)-phenyl-methanone
o
acetate/n-hexane); m.p.=112-113 C (lit. m.p.=112 C) ;
o
1
+
114.6 ppm; MS: m/z 292 [M+H] ; Anal. Calcd for
H
NMR (300 MHz, CDCl3): δ 8.40 (d, J = 8.1 Hz, 1H), 8.23-8.16 C14H8F3N3O: C, 57.74; H, 2.77; N, 14.43. Found: C, 57.91; H,
13
(m, 3H), 7.73-7.67 (m, 2H), 7.61-7.53 (m, 3H); C NMR (75 2.87; N, 14.29.
MHz, CDCl3): δ 166.7, 145.7, 133.6, 132.3, 131.7, 131.6,
131.4, 130.3, 128.4, 126.3, 120.1 and 114.7 ppm; MS: m/z 224 (1
H
-benzo[d][1,2,3]triazol-1-yl)(3,5-
[M+H] ; Anal. Calcd for C13H9N3O: C, 69.95; H, 4.06; N, dichlorophenyl)methanone (2g). White crystalline solid, 1.2
18.82. Found: C, 69.78; H, 4.09; N, 18.7 -hexane x 2);
g, yield 79%; Rf = 0.7 (10% ethyl acetate/
max (cm ) 3068, 2333, 1708, 1564,
1484, 1452, 1420, 1379, 1322, 1291, 1240, 1155, 969, 877,
+
n
o
-1
m.p.=148-152 C; IR (KBr):
ν
(1
white crystalline Solid,1.5g, yield 87%; Rf = 0.7 (10% ethyl
H-benzo[d][1,2,3]triazol-1-yl)(p
-tolyl)methanone(2b).17
1
773, 664; H NMR (300 MHz, CDCl3): δ 8.35 (d,
1H), 8.18 (d, = 8.1Hz, 1H), 8.11 (s, 2H), 7.73 (t,
1H), 7.66 (d, = 1.8Hz, 1H), 7.57 (t,
J
J
= 8.4Hz,
= 7.5Hz,
o
o
1
acetate/
NMR (300 MHz, CDCl3): δ 8.38 (d,
(m, 3H), 7.69 (t, = 7.5Hz, 1H), 7.53 (t,
(d,
= 7.2Hz, 2H), 2.48 (s, 3H); C NMR (75 MHz, CDCl3): δ
n
-hexane); m.p.=123-124 C (lit. m.p.=123 C);
= 8.1Hz, 1H), 8.17-8.12
= 7.5Hz, 1H), 7.38
H
J
13
J
J
J
= 7.5Hz, 1H); C NMR
J
J
(75 MHz, CDCl3): δ 164.1, 145.7, 135.3, 134.0, 133.4, 132.0,
13
J
130.8, 129.9, 126.8, 120.4 and 114.7 ppm; MS: m/z 292
+
[M+H] ; Anal. Calcd for C13H7Cl2N3O: C, 53.45; H, 2.42; N,
166.5, 145.6, 144.8, 131.8, 130.2, 129.1, 128.5, 126.1, 120.0,
+
114.7 and 21.7 ppm; MS: m/z 238 [M+H] ; Anal. Calcd for
14.38. Found: C, 53.71; H, 2.31; N, 14.27.
C14H11N3O: C, 70.87; H, 4.67; N, 17.71. Found: C, 70.63; H,
4.78; N, 17.89.
(1
methoxyphenyl)methanone (2h). White crystalline solid, 1.2
g, yield 72%; Rf = 0.7 (10% ethyl acetate/ -hexane); m.p.=80-
max (cm ) 3105, 3087, 3019, 2963, 2837, 1943,
H-benzo[d][1,2,3]triazol-1-yl)(3-
(1
White crystalline Solid, 1.4g, yield 83%; Rf=0.8 (10% ethyl
H-benzo[d][1,2,3]triazol-1-yl)(m
-tolyl)methanone (2c).18
n
o
-1
84 C; IR (KBr):
ν
o
o
1
-hexane); m.p.=207-209 C (lit. m.p.=205 C); H
acetate/
n
NMR (300 MHz, CDCl3): δ 8.37 (d,
-1
1704, 1585, 1486, 1449, 1367, 951, 746 cm ; MS: m/z 254 [M
J
=8.1Hz, 1H), 8.16 (d,
J
= 7.5Hz, 1H), 7.56-7.43
=
+
1
+ H] ; H NMR (300 MHz, CDCl3): δ 8.34 (d,
8.13 (d, = 8.1Hz, 1H), 7.79 (d, = 7.5Hz, 1H), 7.64-7.70 (m,
2H), 7.54-7.43 (m, 2H), 7.21 (d, = 6.3Hz, 1H), 3.87 (s, 3H);
J
= 8.1Hz, 1H),
8.4Hz, 1H), 7.99 (bs, 2H), 7.69 (t,
13
(m, 3H), 2.47 (s, 3H); C NMR (75 MHz, CDCl3): δ 166.8,
145.7, 138.2, 134.4, 132.3, 132.0, 131.3, 130.2, 128.8, 128.2,
J
J
J
J
+
126.2, 120.1, 114.7 and 21.3 ppm; MS: m/z 238 [M+H] ; Anal.
Calcd for C14H11N3O: C, 70.87; H, 4.67; N, 17.71. Found: C,
70.53; H, 4.71; N, 17.95.
13
C NMR (75 MHz, CDCl3): δ 166.3, 159.2, 145.5, 132.4,
132.2, 130.2, 129.3, 126.1, 124.1, 119.9, 116.0, 114.6, 114.5
and 55.4 ppm.
(1
H-benzo[d][1,2,3]triazol-1-yl)(o-tolyl)methanone
(1
H-benzo[d][1,2,3]triazol-1-yl)(3-phenoxyphenyl)
(2d).White crystalline Solid, 1.5g, yield 88%; Rf=0.8 (10%
methanone (2i). White crystalline solid, 1.19 g, yield 81%; Rf =
1
ethyl acetate/
= 8.1Hz, 1H), 8.15 (d,
7.56-7.47 (m, 2H), 7.34 (t,
n
-hexane); H NMR (300 MHz, CDCl3): δ 8.39 (d,
o
1
0.6 (13% ethyl acetate/
MHz, CDCl3): δ 8.31 (d,
7.91 (d, = 7.5Hz, 1H), 7.81 (s, 1H), 7.67-7.62 (m, 1H), 7.52
(t, = 7.8Hz, 2H), 7.37-7.29 (m, 3H), 7.14-7.05 (m, 3H);
n
-hexane); m.p.=52-53 C; H NMR (300
J
J
= 8.4Hz, 1H), 7.72-7.61 (m, 2H),
J
=8.1Hz, 1H), 8.12 (d, = 8.4Hz, 1H),
J
13
C
J
= 8.1Hz, 3H), 2.43 (s, 3H);
J
NMR (75 MHz, CDCl3): δ 168.1, 146.0, 137.8, 132.2, 131.7,
131.6, 130.9, 130.3, 129.9, 126.3, 125.3, 120.1, 114.5 and 19.9
13
J
C
NMR (75 MHz, CDCl3): δ 165.8, 157.2, 156.1, 145.5, 132.8,
132.0, 130.2, 129.8, 129.6, 126.2, 126.1, 123.9, 123.5, 121.1,
+
ppm; MS: m/z 238 [M+H] .
+
120.0, 119.1 and 114.5 ppm; MS: m/z 316 [M+H] ; Anal. Calcd
(1
H-benzo[d][1,2,3]triazol-1-yl)(4-chlorophenyl)methanone
for C19H13N3O2: C, 72.37; H, 4.16; N, 13.33. Found: C, 72.67;
H, 4.09; N, 13.23.
(2e).19 White crystalline Solid,1.2g, yield 71%; Rf=0.5 (10%
o
o
1
ethyl acetate/
NMR (300 MHz, CDCl3): δ 8.38 (d,
(m, 3H), 7.72 (t, = 7.5Hz, 1H), 7.60–7.55 (m, 3H); C NMR
n
-hexane); m.p.=137-138 C (lit. m.p.=138 C); H
J
= 8.1Hz, 1H), 8.25–8.16
1-(1
White solid, 1.5 g, yield 87%; Rf = 0.7 (5% ethyl acetate/
H-benzo[d
][1,2,3]triazol-1-yl)-2-phenylethanone(2j).17
13
J
n-
(75 MHz, CDCl3): δ 165.6, 145.7, 140.4, 133.1, 130.5, 129.7,
+
128.8, 126.4, 120.2 and 114.8 ppm; MS: m/z 258 [M+H] .
o
o
hexane); m.p.=63-64 C (lit. m.p.=65-66 C); MS: m/z 238 [M +
+
H] ; H NMR (300 MHz, CDCl3): δ 8.24 (d,
1
J
= 8.1Hz, 1H),
8.11 (d, J = 8.4Hz, 1H), 7.61 (t, J = 7.5Hz, 1H), 7.50-7.44 (m,
6 | J. Name., 2012, 00, 1-3
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