1422
I. Yavari, M. Nematpour
LETTER
N-[3-Butyl-4-tosylazet-2(1H)-ylidene]benzene-
(KBr): νmax = 3436, 2925, 1512, 1397, 1278, 1131, 1082 cm–
1. 1H NMR (500 MHz, CDCl3): δ = 2.48 (3 H, s, Me), 5.08
(1 H, s, NH), 7.29-7.36 (3 H, m, Ph), 7.40 (2 H, d, 3J = 7.7
Hz, Ar), 7.49 (2 H, d, 3J = 7.6 Hz, Ar), 7.62 (2 H, t, 3J = 7.7
Hz, Ar), 7.75 (1 H, t, 3J = 7.7 Hz, Ar), 7.91 (2 H, d, 3J = 7.9
Hz, Ar), 8.05 (2 H, d, 3J = 7.9 Hz, Ar). 13C NMR (125.7
MHz, CDCl3): δ = 32.2 (Me), 122.6 (C), 127.4 (2 CH), 127.5
(2 CH), 128.7 (2 CH), 129.2 (CH), 130.1 (2 CH), 130.7 (2
CH), 132.6 (2 CH), 135.7 (C), 136.0 (CH), 142.1 (C), 144.8
(C), 147.3 (C), 164.8 (C), 167.7 (C). MS (EI): m/z (%) = 438
(2) [M+], 361 (14), 347 (13), 283 (16), 196 (14), 155 (100),
141 (68), 91 (55), 77 (44). Anal. Calcd (%) for
sulfonamide (7h)
Yellow oil; yield 0.25 g (60%). IR (KBr): νmax = 3411, 2924,
1518, 1471, 1298, 1145, 1086 cm–1. 1H NMR (500 MHz,
CDCl3): δ = 0.90 (3 H, t, 3J = 6.9 Hz, Me), 1.39–1.45 (2 H,
m, CH2), 1.48–1.53 (2 H, m, CH2), 2.17 (2 H, t, 3J = 7.0 Hz,
CH2), 2.48 (3 H, s, Me), 5.09 (1 H, s, NH), 7.39 (2 H, d, 3J =
7.8 Hz, Ar), 7.62 (2 H, t, 3J = 7.8 Hz, Ar), 7.76 (1 H, t, 3J =
7.8 Hz, Ar), 7.91 (2 H, d, 3J = 8.0 Hz, Ar), 8.05 (2 H, d, 3J =
8.0 Hz, Ar). 13C NMR (125.7 MHz, CDCl3): δ = 14.0 (Me),
18.5 (CH2), 22.1 (CH2), 22.5 (CH2), 31.0 (Me), 122.4 (C),
127.4 (2 CH), 127.5 (2 CH), 130.1 (2 CH), 130.7 (2 CH),
135.7 (CH), 142.1 (C), 144.8 (C), 147.2 (C), 164.9 (C),
167.6 (C). MS (EI): m/z (%) = 418 (2) [M+], 361 (10), 341
(16), 277 (32), 155 (34), 141 (100), 91 (49), 77 (35), 57 (50).
Anal. Calcd (%) for C20H22N2O4S2 (418.10): C, 57.39; H,
5.30; N, 6.69. Found: C, 57.76; H, 5.44; N, 6.75.
N-[3-Butyl-4-tosylazet-2(1H)-ylidene]methane-
sulfonamide (7i)
Yellow oil; yield 0.21 g (58%). IR (KBr): νmax = 3513, 2934,
1524, 1408, 1279, 1118, 1044 cm–1. 1H NMR (500 MHz,
CDCl3): δ = 0.91 (3 H, t, 3J = 6.9 Hz, Me), 1.38–1.43 (2 H,
m, CH2), 1.47–1.51 (2 H, m, CH2), 2.17 (2 H, t, 3J = 7.0 Hz,
CH2), 2.48 (3 H, s, Me), 3.66 (3 H, s, Me), 5.07 (1 H, s, NH),
7.39 (2 H, d, 3J = 7.9 Hz, Ar), 7.91 (2 H, d, 3J = 7.9 Hz, Ar).
13C NMR (125.7 MHz, CDCl3): δ = 13.9 (Me), 18.5 (CH2),
22.1 (CH2), 22.3 (CH2), 31.0 (Me), 33.0 (Me), 122.6 (C),
127.5 (2 CH), 130.7 (2 CH), 142.1 (C), 147.3 (C), 162.2 (C),
167.5 (C). MS (EI): m/z (%) = 356 (2) [M+], 277 (12), 236
(10), 155 (39), 91 (45), 78 (100), 57 (46). Anal. Calcd (%)
for C15H20N2O4S2 (356.46): C, 50.54; H, 5.66; N, 17.86.
Found: C, 50.76; H, 5.74; N, 18.01.
C22H18N2O4S2 (438.07): C, 60.26; H, 4.14; N, 6.39. Found:
C, 60.69; H, 4.21; N, 6.44.
N-[3-Phenyl-4-(phenylsulfonyl)azet-2(1H)-ylidene]-
benzenesulfonamide (7e)
Pale yellow powder, mp 114–117 °C; yield 0.31 g (73%). IR
(KBr): νmax = 3450, 2922, 1511, 1264, 1140, 1082 cm–1. 1H
NMR (500 MHz, CDCl3): δ = 5.06 (1 H, s, NH), 7.31–7.36
(5 H, m, Ph), 7.51–7.53 (3 H, m, Ph), 7.59 (2 H, t, 3J = 7.7
Hz, Ar), 7.72 (1 H, t, 3J = 7.7 Hz, Ar), 7.98 (2 H, d, 3J = 7.9
Hz, Ar), 8.05 (2 H, d, 3J = 7.9 Hz, Ar). 13C NMR (125.7
MHz, CDCl3): δ = 122.6 (C), 127.4 (2 CH), 127.9 (2 CH),
128.8 (2 CH), 129.3 (CH), 130.2 (2 CH), 130.7 (CH), 132.6
(2 CH), 135.3 (CH), 135.7 (2 CH), 139.0 (C), 142.2 (C),
144.8 (C), 166.4 (C), 168.3 (C). MS (EI): m/z (%) = 424 (3)
[M+], 347 (13), 283 (8), 242 (10), 182 (21), 141 (100), 77
(34). Anal. Calcd (%) for C21H16N2O4S2 (424.06): C, 59.42;
H, 3.80; N, 6.60. Found: C, 59.69; H, 3.84; N, 6.57.
N-[3-Phenyl-4-(phenylsulfonyl)azet-2(1H)-ylidene]-
methanesulfonamide (7f)
Pale yellow powder, mp 90–93 °C; yield 0.25 g (70%). IR
(KBr): νmax = 3439, 1513, 1269, 1145, 1086 cm–1. 1H NMR
(500 MHz, CDCl3): δ = 3.60 (3 H, s, Me), 5.08 (1 H, s, NH),
7.29–7.36 (3 H, m, Ph), 7.47 (2 H, d, 3J = 7.7 Hz, Ar), 7.63
(2 H, t, 3J = 7.8 Hz, Ar), 7.74 (1 H, t, 3J = 7.8 Hz, Ar), 8.04
(2 H, d, 3J = 7.8 Hz, Ar). 13C NMR (125.7 MHz, CDCl3): δ
= 33.0 (Me), 122.5 (C), 127.4 (2 CH), 128.8 (2 CH), 129.3
(CH), 130.2 (2 CH), 132.6 (2 CH), 135.7 (CH), 142.3 (C),
147.8 (C), 164.6 (C), 167.4 (C). MS (EI): m/z (%) = 362 (2)
[M+], 285 (11), 242 (18), 221 (21), 141 (54), 78 (100), 77
(25). Anal. Calcd (%) for C16H14N2O4S2 (362.04): C, 53.02;
H, 3.89; N, 7.73. Found: C, 53.41.; H, 3.94; N, 7.80.
N-[3-Butyl-4-tosylazet-2(1H)-ylidene]-4-methylbenzene-
sulfonamide (7g)
(6) Whiting, M.; Fokin, V. V. Angew. Chem. Int. Ed. 2006, 45,
3157.
(7) Xu, X.; Cheng, D.; Li, J.; Guo, H.; Yan, J. Org. Lett. 2007,
9, 1585.
(8) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K.
B. Angew. Chem. Int. Ed. 2002, 41, 2596.
(9) Wang, J.; Wang, J.; Zhu, Y.; Lu, P.; Wang, Y. Chem.
Commun. 2011, 47, 3275.
(10) Cui, S. L.; Wang, J.; Wang, Y. G. Tetrahedron 2008, 64,
487.
(11) Yavari, I.; Nematpour, M. Synlett 2012, 23, 2215.
(12) Yavari, I.; Nematpour, M.; Yavari, S.; Sadeghizadeh, F.
Tetrahedron Lett. 2012, 53, 1889.
Yellow oil; yield 0.29 g (67%). IR (KBr): νmax = 3452, 2932,
1525, 1461, 1278, 1118 cm–1. 1H NMR (500 MHz, CDCl3):
δ = 0.91 (3 H, t, 3J = 6.9 Hz, Me), 1.28–1.45 (2 H, m, CH2),
1.47–1.53 (2 H, m, CH2), 2.18 (2 H, t, 3J = 7.0 Hz, CH2), 2.43
(3 H, s, Me), 2.48 (3 H, s, Me), 5.10 (1 H, s, NH), 7.39–7.41
(4 H, m, Ph), 7.83 (2 H, d, 3J = 8.0 Hz, Ar), 7.91 (2 H, d, 3J
= 8.0 Hz, Ar). 13C NMR (125.7 MHz, CDCl3): δ = 13.9 (Me),
18.5 (CH2), 22.1 (CH2), 22.2 (CH2), 31.0 (Me), 32.3 (Me),
122.2 (C), 127.5 (2 CH), 128.0 (2 CH), 130.6 (2 CH), 130.7
(2 CH), 132.3 (C), 136.0 (C), 144.3 (C), 146.6 (C), 162.6
(C), 166.2 (C). MS (EI): m/z (%) = 432 (2) [M+], 375 (16),
341 (13), 277 (21), 196 (31), 155 (100), 91 (51), 77 (41), 57
(52). Anal. Calcd (%) for C21H24N2O4S2 (432.12): C, 58.31;
H, 5.59; N, 6.48. Found: C, 58.71; H, 5.65; N, 6.55.
(13) Yavari, I.; Nematpour, M.; Ghazanfarpour-Darjani, M.
Tetrahedron Lett. 2012, 53, 942.
(14) Yavari, I.; Nematpour, M. Mol. Diversity 2012, 16, 651.
(15) Recently, Sharpless and co-workers established anhydrous
conditions with CuI in CHCl3/2,6-lutidine at 0 °C to prevent
intermediate 9 from decomposing and provide selective
formation of the desired 1-sulfonyltriazoles. See: Yoo, E. J.;
Ahlquist, M.; Kim, S. H.; Bae, I.; Fokin, V. V.; Sharpless, K.
B.; Chang, S. Angew. Chem. Int. Ed. 2007, 46, 1730.
(16) Cassidy, M. P.; Raushel, J.; Fokin, V. V. Angew. Chem. Int.
Ed. 2006, 45, 3154.
(17) Lu, P.; Wang, Y. Synlett 2010, 165.
(18) Yao, W.; Pan, L.; Zhang, Y.; Wang, G.; Wang, X.; Ma, C.
Angew. Chem. Int. Ed. 2010, 49, 9210.
Synlett 2013, 24, 1420–1422
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