218
S. Kumar/Chemical Papers 66 (3) 216–220 (2012)
Table 3. Spectral data of 5-aryl-2-(arylamino)-1,3,4-oxadiazoles (III)
Compound
Spectral dataa
IR, ν˜/cm−1: 3230, 3045, 1607 (C N), 1265, 1069 (C—O—C), 910, 860, 735
—
IIIa
—
1H NMR (CDCl3), δ: 10.25 (s, 1H, NH), 8.76 (s, 1H, ArH), 7.91 (d, 1H, J = 8.6 Hz, ArH), 7.75 (d, 1H, J = 8.6 Hz,
ArH), 7.47–7.29 (m, 5H, ArH)
13C NMR (CDCl3), δ: 176.3 (C-2), 159.8 (C-5), 148.1 (C-1ꢀ), 139.8 (C-1ꢀꢀ), 135.1 (C-3ꢀꢀ), 129.8 (C-3ꢀ, C-5ꢀ), 129.4
(C-5ꢀꢀ), 127.1 (C-4ꢀꢀ), 125.7 (C-6ꢀꢀ), 124.9 (C-2ꢀꢀ), 119.0 (C-4ꢀ), 116.1 (C-2ꢀ, C-6ꢀ)
MS (ESI), m/z: 307.15 [M + H]+
—
IIIb
IIIc
IIId
IIIe
IR, ν˜/cm−1: 3250, 3045, 2855, 1607 (C N), 1265, 1069 (C—O—C), 910, 860, 735
—
1H NMR (CDCl3), δ: 10.35 (s, 1H, NH), 8.78 (s, 1H, ArH), 7.99–7.28 (m, 5H, ArH), 7.89 (d, 1H, J = 8.6 Hz, ArH),
7.78 (d, 1H, J = 8.6 Hz, ArH), 2.28 (s, 6H, CH3)
13C NMR (CDCl3), δ: 175.3 (C-2), 159.6 (C-5), 148.4 (C-1ꢀ), 138.9 (C-1ꢀꢀ), 136.5 (C-4ꢀꢀ), 135.9 (C-2ꢀꢀ), 129.7 (C-3ꢀꢀ),
128.8 (C-3ꢀ, C-5ꢀ), 126.3 (C-6ꢀꢀ), 126.1 (C-5ꢀꢀ), 119.1 (C-4ꢀ), 116.2 (C-2ꢀ, C-6ꢀ), 21.2 (CH3)
MS (ESI), m/z: 266.32 [M + H]+
IR, ν˜/cm−1: 3260, 3055, 2855, 1604 (C N), 1255, 1080 (C—O—C), 950, 860, 740
—
—
1H NMR (CDCl3), δ: 10.32 (s, 1H, NH), 7.88–6.97 (m, 5H, ArH), 6.24 (s, 2H, ArH-3,5), 3.78 (s, 3H, 4-OCH3), 3.70
(s, 6H, 2,6-OCH3)
13C NMR (CDCl3), δ: 174.5 (C-2), 160.8 (C-6ꢀꢀ), 160.3 (C-4ꢀꢀ), 160.3 (C-2ꢀꢀ), 157.4 (C-5), 148.4 (C-1ꢀ), 128.8 (C-3ꢀ,
C-5ꢀ), 119.1 (C-4ꢀ), 116.2 (C-2ꢀ, C-6ꢀ), 104.3 (C-1ꢀꢀ), 91.9 (C-3ꢀꢀ), 91.4 (C-5ꢀꢀ), 55.9 (2,6-OCH3), 55.4 (4-OCH3)
MS (ESI), m/z: 328.34 [M + H]+
IR, ν˜/cm−1: 3244, 2927, 2853, 2822, 1611 (C N), 1250, 1062 (C—O—C), 915, 870, 675
—
—
1H NMR (CDCl3), δ: 10.35 (s, 1H, NH), 8.77 (s, 1H, ArH), 7.89 (d, 1H, J = 8.6 Hz, ArH), 7.79 (d, 1H, J = 8.6 Hz,
ArH), 7.45–6.92 (m, 4H, ArH), 3.74 (s, 3H, OCH3)
13C NMR (CDCl3), δ: 174.7 (C-2), 158.5 (C-5), 147.5 (C-2ꢀ), 140.8 (C-1ꢀꢀ), 135.6 (C-3ꢀꢀ), 133.5 (C-1ꢀ), 129.4 (C-5ꢀꢀ),
127.9 (C-4ꢀꢀ), 125.6 (C-6ꢀꢀ), 124.3 (C-2ꢀꢀ), 122.1 (C-5ꢀ), 119.9 (C-4ꢀ), 117.1 (C-6ꢀ), 115.4 (C-3ꢀ), 53.7 (OCH3)
MS (ESI), m/z: 337.18 [M + H]+
IR, ν˜/cm−1: 3261, 3045, 2855, 2815, 1609 (C N), 1270, 1069 (C—O—C), 915, 870, 790
—
—
1H NMR (CDCl3), δ: 10.48 (s, 1H, NH), 8.78 (s, 1H, ArH), 7.89 (d, 1H, J = 8.6 Hz, ArH), 7.78 (d, 1H, J = 8.6 Hz,
ArH), 7.03–6.93 (m, 4H, ArH), 3.11 (s, 3H, OCH3), 2.21 (s, 6H, CH3)
13C NMR (CDCl3), δ: 175.3 (C-2), 159.8 (C-5), 147.5 (C-2ꢀ), 138.8 (C-1ꢀꢀ), 136.5 (C-4ꢀꢀ), 135.9 (C-2ꢀꢀ), 133.5 (C-1ꢀ),
129.4 (C-3ꢀꢀ), 126.5 (C-6ꢀꢀ), 126.2 (C-5ꢀꢀ), 122.3 (C-5ꢀ), 119.3 (C-4ꢀ), 117.6 (C-6ꢀ), 115.1 (C-3ꢀ), 53.8 (OCH3), 21.9
(CH3)
MS (ESI), m/z: 296.34 [M + H]+
—
IIIf
IR, ν˜/cm−1: 3260, 3043, 2860, 2822, 1608 (C N), 1280, 1066 (C—O—C), 925, 890, 785
—
1H NMR (CDCl3), δ: 10.29 (s, 1H, NH), 7.75–6.89 (m, 4H, ArH), 6.24 (s, 2H, ArH3 and H5), 3.78 (s, 3H, OCH3),
3.76 (s, 3H, 4-OCH3), 3.70 (s, 6H, 2,6-OCH3)
13C NMR (CDCl3), δ: 174.5 (C-2), 160.8 (C-6ꢀꢀ), 160.3 (C-4ꢀꢀ), 160.2 (C-2ꢀꢀ), 157.4 (C-5), 147.5 (C-2ꢀ), 133.5 (C-1ꢀ),
122.1 (C-5ꢀ), 119.9 (C-4ꢀ), 117.1 (C-6ꢀ), 115.4 (C-3ꢀ), 104.3 (C-1ꢀꢀ), 91.9 (C-3ꢀꢀ), 91.4 (C-5ꢀꢀ), 55.9 (2,6-OCH3), 55.4
(4-OCH3), 53.8 (OCH3)
MS (ESI), m/z: 359.35 [M + H]+
—
IIIg
IIIh
IIIi
IR, ν˜/cm−1: 3236, 3033, 3030, 2855, 2820, 1670, 1606 (C N), 1262, 1067 (C—O—C), 920, 860, 790
—
1H NMR (CDCl3-d6), δ: 10.32 (s, 1H, NH), 8.76 (s, 1H, ArH), 7.91 (d, 1H, J = 8.6 Hz, ArH), 7.75 (d, 1H, J =
8.6 Hz, ArH), 7.71 (d, 2H, J = 8.6 Hz, ArH), 7.62 (d, 2H, J = 8.6 Hz, ArH), 3.77 (s, 3H, OCH3)
13C NMR (CDCl3), δ: 174.5 (C-2), 157.4 (C-5), 139.6 (C-1ꢀꢀ), 135.6 (C-3ꢀꢀ), 132.6 (C-1ꢀ), 129.2 (C-5ꢀꢀ), 127.8 (C-4ꢀꢀ),
127.5 (C-2ꢀ, C-6ꢀ), 125.8 (C-6ꢀꢀ), 124.5 (C-2ꢀꢀ), 119.5 (C-4ꢀ), 114.1 (C-3ꢀ, C-5ꢀ), 55.5 (OCH3)
MS (ESI), m/z: 337.18 [M + H]+
IR, ν˜/cm−1: 3244, 2927, 2870, 2822, 1611 (C N), 1250, 1062 (C—O—C), 915, 870, 675
—
—
1H NMR (CDCl3), δ: 10.35 (s, 1H, NH), 8.78 (s, 1H, ArH), 7.89 (d, 1H, J = 8.6 Hz, ArH), 7.79 (d, 1H, J = 8.6 Hz,
ArH), 7.71 (d, 2H, J = 8.6 Hz, ArH), 7.63 (d, 2H, J = 8.6 Hz, ArH), 3.74 (s, 3H, OCH3), 2.28 (s, 6H, CH3)
13C NMR (CDCl3), δ: 174.7 (C-2), 158.5 (C-5), 158.3 (C-4ꢀ), 138.5 (C-1ꢀꢀ), 136.5 (C-4ꢀꢀ), 135.9 (C-2ꢀꢀ), 132.5 (C-1ꢀ),
129.8 (C-3ꢀꢀ), 127.5 (C-2ꢀ, C-6ꢀ), 126.8 (C-5ꢀꢀ), 126.6 (C-6ꢀꢀ), 114.1 (C-3ꢀ, C-5ꢀ), 55.3 (OCH3), 21.2 (CH3)
MS (ESI), m/z: 296.34 [M + H]+
IR, ν˜/cm−1: 3244, 2927, 2870, 2815, 1611 (C N), 1250, 1062 (C—O—C), 915, 870, 675
—
—
1H NMR (CDCl3), δ: 10.35 (s, 1H, NH), 8.24 (s, 2H, ArH), 7.79 (d, 2H, J = 8.6 Hz, ArH), 7.71 (d, 2H, J = 8.6 Hz,
ArH), 3.78 (s, 3H, 4-OCH3), 3.75 (s, 3H, OCH3), 3.70 (s, 6H, 2,6-OCH3)
13C NMR (CDCl3), δ: 174.7 (C-2), 160.8 (C-6ꢀꢀ), 160.5 (C-4ꢀꢀ), 160.2 (C-2ꢀꢀ), 158.5 (C-5), 141.3 (C-1ꢀ), 136.0 (C-2ꢀ),
129.3 (C-3ꢀ), 126.8 (C-4ꢀ), 126.7 (C-6ꢀ), 125.8 (C-5ꢀ), 104.2 (C-1ꢀꢀ), 91.9 (C-3ꢀꢀ), 91.4 (C-5ꢀꢀ), 55.2 (4-OCH3), 54.9
(2,6-OCH3)
MS (ESI), m/z: 359.35 [M + H]+
IR, ν˜/cm−1: 3244, 2927, 2870, 1611 (C N), 1250, 1062 (C—O—C), 915, 870, 675
—
IIIj
—
1H NMR (CDCl3), δ: 10.36 (s, 1H, NH), 8.75 (s, 1H, ArH), 7.91 (d, 1H, J = 8.6 Hz, ArH), 7.75 (d, 1H, J = 8.6 Hz,
ArH), 7.45–7.35 (m, 4H, ArH), 1.12 (s, 3H, CH3)
13C NMR (CDCl3), δ: 174.7 (C-2), 158.5 (C-5), 141.3 (C-1ꢀ), 140.1 (C-1ꢀꢀ), 136.1 (C-2ꢀ), 135.6 (C-3ꢀꢀ), 129.4 (C-5ꢀꢀ),
129.3 (C-3ꢀ), 127.5 (C-4ꢀꢀ), 126.8 (C-4ꢀ), 126.7 (C-6ꢀ), 125.8 (C-5ꢀ), 125.6 (C-6ꢀꢀ), 124.9 (C-2ꢀꢀ), 21.18 (CH3)
MS (ESI), m/z: 321.18 [M + H]+