5346
I. R. Baxendale et al. / Tetrahedron 61 (2005) 5323–5349
HY-2/6), 8.00 (2H, d, JZ8.8 Hz, HY-3/5), 7.84 (1H, dd,
JZ7.9, 1.6 Hz, HZ-Ar), 7.63 (2H, m, HZ-Ar), 7.54 (1H, m,
HZ-Ar), 7.31 (1H, t, JZ7.9 Hz, HX-4), 7.22 (2H, d,
JZ7.6 Hz, HX-3/5), 2.10 (6H, s, 2!Me); 13C NMR
(d6-DMSO; 125 MHz) d ppm 160.52 (C), 158.41 (C),
138.96 (C), 137.29 (C), 134.36 (C), 133.88 (CH), 133.36
(CH), 132.11 (C), 131.75 (CH), 131.48 (CH), 131.27 (CH),
130.62 (CH), 129.92 (C), 129.77 (CH), 128.40 (CH), 122.49
(C), 18.48 (CH3). IR n (neat)Z1563.2 (s), 1539.8 (m),
1462.9 (w), 1444.5 (w), 1368.5 (s), 1290.6 (m), 1279.6 (m),
1188.8 (w), 1166.0 (s), 1083.6 (w), 1066.9 (w), 932.7 (m),
129.29 (CH), 128.96 (CH), 128.09 (CH), 127.67 (CH),
126.92 and 126.89 and 126.86 and 126.83 (CF3). IR n
(neat)Z1571.3 (w), 1537.7 (s), 1505.9 (w), 1472.4 (w),
1449.9 (w), 1424.9 (w), 1367.2 (w), 1327.9 (s), 1285.5 (w),
1181.6 (m), 1161.1 (s), 1123.8 (m), 1095.6 (s), 1068.9 (s),
1015.3 (m), 968.5 (m), 946.4 (m), 925.6 (w), 847.4 (s),
788.9 (m), 745.0 (m), 719.3 (s), 679.8 (s) cmK1. HR-MS
Calcd for C20H14N3O3ClF3S: 480.0347; found 480.0401.
4.3.51. 3,4-Dimethoxybenzenesulfonic acid 3-{5-[(3,4-di-
methoxy-benzenesulfonyl)-(2,6-dimethylphenyl)-amino]-
[1,3,4]oxadiazol-2-yl}naphthalen-2-yl ester 93. H NMR
826.9 (m), 782.4 (m), 763.1 (s), 740.8 (s), 727.5 (s) cmK1
.
1
HRMS Calcd for C22H18N3O3SBr2 561.9436; found
561.9388.
(d6-DMSO; 500 MHz) d ppm 8.44 (1H, s), 8.12 (1H, dd, JZ
7.9 Hz), 8.03 (1H, d, JZ7.9 Hz), 7.90 (1H, s), 6.68 (3H, m),
7.33 (1H, m), 7.29 (1H, d, JZ8.8 Hz), 7.23 (2H, m), 7.17
(1H, dd, JZ8.5, 2.5 Hz), 7.08 (1H, d, JZ2.2 Hz), 6.98 (1H,
d, JZ8.8 Hz), 3.91 (3H, s, OMe), 3.81 (6H, s, 2!OMe),
3.60 (3H, s, OMe), 2.13 (6H, s, 2!Me); 13C NMR
(d6-DMSO; 125 MHz) d ppm 159.68 (C), 158.83 (C),
154.60 (C), 154.58 (C), 149.25 (C), 149.23 (C), 142.86 (C),
139.12 (C), 134.81 (C), 134.42 (C), 131.93 (CH), 131.13
(C), 130.40 (CH), 129.79 (CH), 129.67 (CH), 129.27 (C),
129.12 (CH), 128.39 (CH), 128.35 (CH), 124.87 (C), 123.79
(CH), 123.17 (CH), 122.42 (CH), 116.65 (C), 112.03 (CH),
111.69 (CH), 111.57 (CH), 110.81 (CH), 56.60 (CH3), 56.46
(CH3), 56.32 (CH3), 56.09 (CH3), 18.47 (CH3). IR n
(neat)Z1630.3 (w), 1582.9 (m), 1544.4 (m), 1508.2 (s),
1464.3 (m), 1441.8 (m), 1407.5 (m), 1369.6 (s), 1264.3 (s),
1238.2 (s), 1188.5 (m), 1174.0 (m), 1163.4 (m), 1140.5 (s),
1092.2 (s), 1054.3 (w), 1013.5 (s), 928.3 (w), 911.8 (m),
4.3.48. 3-[(4-Bromobenzenesulfonyl)-(5-pyridin-3-yl-
[1,3,4]oxadiazol-2-yl)-amino]benzoic acid methyl ester
90. 1H NMR (d6-DMSO; 500 MHz) d ppm 9.04 (1H, dd, JZ
2.2, 0.95 Hz, HZ-2), 8.81 (1H, dd, JZ4.7, 1.6 Hz, HZ-4),
8.26 (1H, ddd, JZ7.9, 2.2, 1.6 Hz, HZ-6), 8.10 (1H, m,
HZ-Ar), 7.98 (2H, d, JZ8.8 Hz, HX-3/5), 7.96 (1H, m), 7.84
(2H, d, JZ8.8 Hz, HX-2/6), 7.68 (2H, m, 2!HY-Ar), 7.63
(1H, ddd, JZ7.9, 4.7, 0.95 Hz, HZ-5), 3.88 (3H, s, OMe);
13C NMR (d6-DMSO; 125 MHz) d ppm 165.47 (C), 161.91
(C), 158.54 (C), 153.17 (CH), 147.51 (CH), 136.57 (C),
135.79 (C), 134.57 (CH), 134.07 (CH), 133.43 (CH), 131.75
(C), 131.13 (CH), 131.11 (CH), 130.90 (CH), 129.96 (CH),
129.92 (C), 124.82 (CH), 120.04 (C), 53.04 (CH3). IR n
(neat)Z1716.4 (s), 1606.7 (w), 1583.4 (w), 1572.6 (m),
1563.1 (m), 1540.4 (s), 1484.0 (m), 1467.6 (m), 1432.8 (m),
1406.0 (m), 1388.6 (m), 1368.0 (m), 1294.9 (s), 1274.1 (s),
1207.7 (m), 1169.3 (s), 1159.6 (s), 1099.5 (m), 1083.1 (m),
1064.8 (m), 1016.9 (w), 1004.2 (m), 993.4 (m), 960.5 (m),
891.9 (m), 829.2 (m), 755.1 (m), 745.8 (s), 720.0 (s),
699.9 (s), 686.5 (s), 654.0 (m) cmK1. HRMS Calcd for
C21H16N4O5SBr 515.00225; found 515.0037.
893.8 (m), 854.8 (w), 817.4 (m), 765.9 (s), 741.2 (m) cmK1
.
HRMS Calcd for C36H34N3O10S2 732.1686; found
732.1684.
4.3.52. N-Benzyl-N-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-
yl)benzenesulfonamide 94. 1H NMR (d6-DMSO;
500 MHz) d ppm 9.10 (1H, dd, JZ2.5, 0.95 Hz, HZ-2),
8.72 (1H, dd, JZ5.0, 1.6 Hz, HZ-4), 8.30 (1H, ddd, JZ8.2,
2.2, 1.6 Hz, HZ-6), 8.00 (2H, dd, JZ7.25, 0.95 Hz, HY-2/6),
8.81 (1H, m, HY-4), 7.69 (2H, m, HY-3/5), 7.56 (1H, ddd,
JZ8.2, 5.0, 0.95 Hz, HZ-5), 7.40 (2H, m, 2!HX-Ar), 7.33
(2H, m, 2!HX-Ar), 7.29 (1H, m, HX-Ar), 5.23 (2H, s,
NCH2); 13C NMR (d6-DMSO; 125 MHz) d ppm 162.95 (C),
161.85 (C), 152.29 (CH), 148.19 (CH), 137.10 (C), 135.82
(C), 135.41 (CH), 135.16 (CH), 130.57 (CH), 128.97 (CH),
128.31 (CH), 128.28 (CH), 127.72 (CH), 126.13 (C), 124.74
(CH), 53.10 (CH2). IR n (neat)Z1584.6 (w), 1570.1 (w),
1494.8 (w), 1444.0 (s), 1413.5 (s), 1366.8 (s), 1336.2 (m),
1275.3 (m), 1252.8 (m), 1185.5 (m), 1166.3 (s), 1105.1 (m),
1088.8 (m), 1077.7 (m), 1025.6 (m), 1012.4 (s), 983.0 (m),
971.9 (m), 832.6 (s), 820.7 (m), 806.0 (m), 760.1 (s), 722.0
(s) cmK1. HR-MS Calcd for C20H17N4O3S: 393.1021;
found 393.1014.
4.3.49. N-Adamantan-1-yl-N-(5-hexyl-[1,3,4]oxadiazol-
2-yl)benzenesulfonamide 91. 1H NMR (d6-DMSO;
500 MHz) d ppm 8.26 (2H, d, JZ9.1 Hz, HX-3/5), 7.81
(2H, d, JZ9.1 Hz, HX-2/6), 2.60 (2H, t, JZ7.25 Hz, HZ-1-
CH2), 2.04 (3H, m), 1.91 (5H, m), 1.60 (8H, m), 1.26 (8H,
m), 0.83 (3H, t, JZ6.9 Hz, HZ-Me); 13C NMR (d6-DMSO;
125 MHz) d ppm 161.97 (C), 147.24 (C), 144.06 (C), 142.61
(C), 127.28 (CH), 125.03 (CH), 41.40 (CH2), 36.35 (CH2),
31.56 (CH2), 29.33 (CH), 28.74 (CH2), 28.67 (CH2), 26.42
(CH2), 24.86 (CH2), 22.49 (CH2), 14.38 (CH3). IR n
(neat)Z2903.7 (s), 2850.1 (s), 1625.9 (s), 1573.3 (s),
1515.5 (w), 1468.9 (w), 1454.3 (w), 1389.7 (w), 1361.6 (m),
1334.3 (m), 1307.2 (m), 1249.0 (w), 1225.3 (w), 1180.2 (m),
1136.3 (w), 976.0 (w), 932.1 (m), 852.7 (m), 817.0 (w),
727.8 (m) cmK1. HRMS Calcd for C25H35N4O5S 503.2328;
found 503.2298.
4.3.50. N-(3-Chlorophenyl)-N-[5-(4-trifluoromethyl-
phenyl)-[1,3,4]oxadiazol-2-yl]benzenesulfonamide 92.
1H NMR (d6-DMSO; 500 MHz) d ppm 8.11 (2H, d, JZ
8.2 Hz), 7.96 (3H, m), 7.88 (1H, m), 7.74 (2H, m), 7.61 (1H,
ddd, JZ8.0, 2.1, 1.1 Hz, HX-Ar), 7.54 (1H, t, JZ8.0 Hz,
HX-Ar), 7.51 (1H, t, JZ2.1 Hz, HX-Ar), 7.39 (1H, ddd, JZ
8.0, 2.1, 1.1 Hz, HX-Ar); 13C NMR (d6-DMSO; 125 MHz) d
ppm 162.39 (C), 158.69 (C), 137.47 (C), 136.66 (C), 135.66
(CH), 134.15 (C), 131.79 (CH), 130.61 (CH), 130.28 (CH),
4.3.53. N-Benzyl-4-chloro-N-(5-pyridin-3-yl-[1,3,4]-
oxadiazol-2-yl)benzenesulfonamide 95. 1H NMR
(d6-DMSO; 500 MHz) d ppm 9.06 (1H, dd, JZ2.2,
0.95 Hz, HZ-2), 8.69 (1H, dd, JZ4.7, 1.6 Hz, HZ-4), 8.22
(1H, ddd, JZ7.9, 2.2, 1.6 Hz, HZ-6), 7.90 (2H, d, JZ
8.8 Hz, HY-2/6), 7.61 (2H, d, JZ8.8 Hz, HY-3/5), 7.50 (1H,
ddd, JZ7.9, 4.7, 0.95 Hz, HZ-5), 7.40 (2H, m, 2!HX-Ar),
7.29 (3H, m, 3!HX-Ar), 5.20 (2H, s, HX-1); 13C NMR
(d6-DMSO; 125 MHz) d ppm 162.86 (C), 161.58 (C),