SYNTHESIS AND ANTIMICROBIAL ACTIVITY
829
122.3, 123.3, 126.9, 128.8, 129.0, 129.1, 129.4, 130.4,
131.3, 138.7, 138.9, 139.7, 158.0, 158.6. ESI-MS:
330.06 [M + H]+. Calculated for C15H13ClN5OS.
spectrum, δ, ppm: 18.3, 25.2, 126.4, 126.6, 127.6,
127.7, 128.7, 129.7, 135.2, 135.3, 135.8, 138.3, 138.4,
157.1, 157.6, 158.6, 159.4, 183.2, 184.4. ESI-MS:
324.68 [M + H]+. Calculated for C17H18N5S.
1-(2,6-Diisopropyl-4-phenoxyphenyl)-4-[(3,4-
dimethylphenyl)imino]-6-imino-1,3,5-triazinane-2-
thione (3e). mp 269–270°C. IR spectrum, ν, cm–1:
3656, 3594, 3582, 3208, 2867, 2354, 2088, 1713,
1-(2,6-Diisopropyl-4-phenoxyphenyl)-6-imino-4-
{[2-(trifluoromethoxy)phenyl]imino}-1,3,5-triazi-
nane-2-thione (3i). mp 254–256°C. IR spectrum, ν,
cm–1: 3594, 3437, 3216, 3080, 2929, 2422, 2083, 1895,
1715, 1554, 1370, 1212, 1045, 883, 753, 648, 521,
1
1488, 1295, 1105, 1009, 872, 737, 515, 405. H NMR
spectrum, δ, ppm: 1.11 d (J = 7.0 Hz, 6H), 1.15 d (J =
6.5 Hz, 6H), 2.55–2.59 m (2H), 6.66 s (1H, NH), 6.88
s (2H, С6H5), 7.04 d (J = 8.0 Hz, 1H, С6H5), 7.13–7.24
m (3H, С6H5), 7.58–7.61 m (1H, С6H5), 8.26 s (1H,
NH), 9.94 s (1H, NH). 13C NMR spectrum, δ, ppm:
18.7, 19.6, 23.6, 23.7, 28.5, 114.6, 118.0, 118.4, 121.6,
123.3, 128.1, 129.3, 129.9, 130.6, 136.2, 136.7, 147.2,
156.4, 157.2, 157.8, 158.1, 183.2. ESI-MS: 500.91
[M + H]+. Calculated for C29H34N5OS.
1
407. H NMR spectrum, δ, ppm: 1.09 d (J = 6.5 Hz,
6H), 1.14 d (J = 6.5 Hz, 6H), 2.19–2.23 m (6H), 2.52–
2.57 m (2H), 6.13 s (1H, NH), 6.87 s (2H, С6H5), 7.12–
7.16 m (3H, С6H5), 7.30–7.33 m (1H, С6H5), 7.38–7.43
m (4H, С6H5), 7.75 d (J = 7.5 Hz, 1H, С6H5), 8.08 s
(1H, NH), 9.56 s (1H, NH). 13C NMR spectrum, δ,
ppm: 14.0, 20.5, 20.6, 20.7, 23.6, 24.7, 26.3, 28.5,
34.1, 54.8, 59.7, 114.9, 118.3, 120.7, 121.1, 123.2,
126.4, 127.2, 128.0, 128.1, 129.9, 130.6, 142.5, 147.1,
156.5, 157.1, 157.9, 159.1, 184.2. ESI-MS: 556.85
[M + H]+. Calculated for C28H29F3N5O2S.
4-[(3,4-Dimethylphenyl)imino]-6-imino-1-phenyl-
1,3,5-triazinane-2-thione (3f). mp 206–210°C. IR
spectrum, ν, cm–1: 3665, 3643, 3456, 3332, 2921,
1942, 1715, 1452, 1264, 1107, 966, 756, 609, 444,
6-Imino-1-phenyl-4-{[2-(trifluoromethoxy)phenyl]-
imino}-1,3,5-triazinane-2-thione (3j). mp 233– 235°C.
IR spectrum, ν, cm–1: 3592, 3426, 3371, 3167, 2886,
2329, 1955, 1808, 1654, 1338, 1182, 1049, 955, 775,
628, 498, 407. 1H NMR spectrum, δ, ppm: 6.32 s (1H,
NH), 7.04–7.30 m (3H, С6H5), 7.38–7.44 (m, 3H,
С6H5), 7.50 t (J = 7.0 Hz, 2H, С6H5), 7.80 d (J =
7.5 Hz, 1H, С6H5), 8.02 s (1H, NH), 9.60 s (1H, NH).
13C NMR spectrum, δ, ppm: 21.1, 117.0, 119.1, 121.1,
126.2, 127.3, 127.8, 128.1, 128.6, 128.9, 129.8, 130.8,
138.2, 142.1, 157.6, 159.0, 172.2, 184.1. ESI-MS:
380.59 [M + H]+. Calculated for C16H13F3N5OS.
1
401. H NMR spectrum, δ, ppm: 2.17 s (3H), 2.20 s
(3H), 6.38 s (1H, NH), 7.02–7.04 (m, 1H, С6H5), 7.26–
7.30 (m, 2H, С6H5), 7.42–7.57 m (4H, С6H5), 7.79 d
(J = 7.5 Hz, 1H, С6H5), 8.19 s (1H, NH), 9.94 s (1H,
NH). ESI-MS: 324.65 [M + H]+. Calculated for
C17H18N5S.
1-(2,6-Diisopropyl-4-phenoxyphenyl)-4-[(2,6-di-
methylphenyl)imino]-6-imino-1,3,5-triazinane-2-thione
(3g). mp 263–265°C. IR spectrum, ν, cm–1: 3576,
3414, 3303, 3167, 3074, 2670, 2085, 1841, 1585,
1
1332, 1162, 1030, 879, 718, 579, 499, 427. H NMR
spectrum, δ, ppm: 1.07-1.17 m (12H), 2.19–2.23 m
(6H), 2.53–2.57 m (2H), 6.41 s (1H, NH), 6.87 s (2H,
С6H5), 7.11–7.16 m (6H, С6H5), 7.38–7.43 m (2H,
С6H5), 8.00 s (1H, NH), 9.29 s (1H, NH). 13C NMR
spectrum, δ, ppm: 18.1, 18.2, 23.5, 23.6, 28.5, 114.7,
115.0, 118.1, 118.3, 123.1, 126.6, 127.7, 127.8, 129.8,
129.9, 135.1, 135.7, 147.1, 147.2, 156.7, 156.9, 157.9,
159.3, 183.3. ESI-MS: 500.91 [M + H]+. Calculated for
C29H34N5OS.
CONCLUSIONS
A mild and highly efficient protocol for the
synthesis of 1-aryl-4-(arylimino)-6-iminohexahydro-
1,3,5-triazine-2-thione
derivatives
under
MW
irradiation is developed. The method is characterized
by short reaction time and high yields. The synthesized
1,3,5-triazine derivatives 3a–3j are evaluated for their
antimicrobial activity. Among these 3i and 3j
demonstrate very good antibacterial activity. The other
products show moderate microbial activity against the
tested organisms.
4-[(2,6-Dimethylphenyl)imino]-6-imino-1-phenyl-
1,3,5-triazinane-2-thione (3h). mp 246-248°C. IR
spectrum, ν, cm–1: 3583, 3501, 3303, 3158, 3008,
2674, 2327, 1970, 1841, 1558, 1154, 1001, 837, 661,
471, 424, 411. 1H NMR spectrum, δ, ppm: 2.19 s (3H),
2.22 s (3H), 6.10 s (1H, NH), 7.08–7.10 (m, 3H,
С6H5), 7.22–7.25 (m, 2H, С6H5), 7.38–7.48 m (3H,
С6H5), 8.00 s (1H, NH), 9.30 s (1H, NH). 13C NMR
AKNOWLEDGMENTS
The authors are thankful to the Chairman, Vignan
University, Guntur, India and the Managing Director,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 89 No. 4 2019