H, Tol), 6.91 (d, J = 9.2 Hz, 2 H, Tol), 7.37-7.44 (m, 3 H, Ph), 7.45 (dd, J = 0.8, 1.8 Hz, 1 H, Fur), 7.59-7.61 (m,
2 H, Ph) ppm; 13C NMR (CDCl3, 151 MHz): = 20.5 (q, Me), 88.7 (s, C-2), 110.7, 113.6 (2 d, 2 CH, Fur), 118.4
1
(d, 2 CH, Tol), 119.8 (q, JC-F = 271.1 Hz, CF3), 127.4, 128.7 (2 d, 4 CH, Ph), 128.9 (d, 2 CH, Tol), 129.0 (d,
2
CH, Ph), 130.0 (q, JC-F = 40.7 Hz, C-4), 132.5, 139.5, 139.7 (3 s, 3 i-C, Tol, Ph), 144.2, 150.2 (d, s, CH, i-C,
Fur) ppm; 19F NMR (CDCl3, 188 MHz): = –63.48 (s, CF3) ppm; IR (KBr): = 3139–2917 (=C-H, C-H), 1562,
1508, 1264, 1168-1095 (CF3) cm-1; ESI-MS (m/z): 389 (100, [M+H]+); elemental analysis calcd (%) for
C20H15F3N2OS (388.1): C 61.85, H 3.89, N 7.21, S 8.26; found: C 61.88, H 4.07, N 7.18, S 8.03.
4.3.7. 2-Phenyl-2-(thien-2-yl)-3-p-tolyl-5-trifluoromethyl-2,3-dihydro-1,3,4-thiadiazole (6g)
Reaction time 30 min; 291 mg (72%); pale yellow crystals, mp 117-118 °C. 1H NMR (CDCl3, 600 MHz): =
2.21 (s, 3 H, Me), 6.87 (mc, 4 H, Tol), 6.88 (dd, J = 3.7, 5.2 Hz, 1 H, Th), 6.97 (dd, J = 1.3, 3.7 Hz, 1 H, Th),
7.35 (dd, J = 1.3, 5.2 Hz, 1 H, Th), 7.37-7.43, 7.65-7.68 (2 m, 3 H, 2 H, Ph) ppm; 13C NMR (CDCl3, 151 MHz):
= 20.6 (q, Me), 91.7 (s, C-2), 119.7 (d, 2 CH, Tol), 119.8 (q, 1JC-F = 271.0 Hz, CF3), 126.6 (d, CH, Th), 127.6,
2
128.5 (2 d, 4 CH, Ph), 128.6 (d, CH, Th), 128.9 (d, 2 CH, Tol), 129.0 (d, CH, Ph), 130.1 (q, JC-F = 40.7 Hz, C-
4), 130.3 (d, CH, Th), 133.3 139.5 (2 s, 2 i-C, Tol), 140.8 (s, i-C, Ph), 144.0 (s, i-C, Th) ppm; 19F NMR (CDCl3,
188 MHz): = –63.52 (s, CF3) ppm; IR (KBr): = 3102–2863 (=C-H, C-H), 1563, 1508, 1271, 1155-1100 (CF3)
cm-1; ESI-MS (m/z): 427 (41, [M+Na]+), 405 (100, [M]+); elemental analysis calcd (%) for C20H15F3N2S2
(404.1): C 59.39, H 3.74, N 6.93, S 15.86; found: C 59.35, H 3.76, N 6.88, S 15.78. Suitable crystals for an X-
ray crystal structure determination were obtained from petroleum ether solution by slow evaporation of the
solvent.
4.3.8. 2-Phenyl-2-(selenophen-2-yl)-3-p-tolyl-5-trifluoromethyl-2,3-dihydro-1,3,4-thiadiazole (6h)
Reaction time 45 min; 362 mg (80%); pale yellow crystals, mp 132-134 °C. 1H NMR (CDCl3, 600 MHz): =
2.22 (s, 3 H, Me), 6.90 (mc, 4 H, Tol), 7.11-7.14 (m, 2 H, Sel), 7.37-7.42, 7.66-7.69 (2 m, 3 H, 2 H, Ph), 8.07
(dd, J = 2.2, 4.7 Hz, 1 H, Th) ppm; 13C NMR (CDCl3, 151 MHz): = 20.6 (q, Me), 93.7 (s, C-2), 119.8 (q, 1JC-F
= 271.0 Hz, CF3), 119.9 (d, 2 CH, Tol), 127.7, 128.5 (2 d, 4 CH, Ph), 128.9 (d, 2 CH, Tol), 129.0 (d, CH, Sel),
2
129.1 (d, CH, Ph), 130.0 (q, JC-F = 40.7 Hz, C-4), 132.4 (d, CH, Sel), 133.4 (s, i-C, Tol), 134.8 (d, CH, Sel),
139.4 (s, i-C, Tol), 140.8 (s, i-C, Ph), 151.0 (s, i-C, Sel) ppm; 19F NMR (CDCl3, 188 MHz): = –63.49 (s, CF3)
ppm; IR (KBr): = 3091–2851 (=C-H, C-H), 1562, 1508, 1277, 1165-1115 (CF3) cm-1; ESI-MS (m/z): 453 (100,
[M+H]+); elemental analysis calcd (%) for C20H15F3N2SSe (452.0): C 53.22, H 3.35, N 6.21, S 7.10; found: C
52.99, H 3.34, N 6.25, S 7.12.
4.3.9. 2-Ferrocenyl-2-methyl-3-p-tolyl-5-trifluoromethyl-2,3-dihydro-1,3,4-thiadiazole (6i)
1
Reaction time 45 min; 261 mg (59%); orange crystals, mp 105-106 °C. H NMR (CDCl3, 600 MHz): =
1.90 (s, 3 H, Me), 2.24 (s, 3 H, Me), 4.10 (sbr, 1 H, Fc), 4.20 (s, 5 H, Fc), 4.22 (sbr, 1 H, Fc), 4.45 (sbr, 1 H, Fc),
4.93 (sbr, 1 H, Fc), 6.71 (dbr, J 8.3 Hz, 2 H, Tol), 6.91 (dbr, J 8.3 Hz, 2 H, Tol) ppm; 13C NMR (CDCl3, 151
MHz): = 20.8, 25.3 (2 q, 2 Me), 68.5, 69.3 (2 d, 2 CH, Fc), 69.5 (d, 6 CH, Fc), 70.4 (d, CH, Fc), 87.8 (s, i-C,
Fc), 91.5 (s, C-2), 120.0 (q, 1JC-F = 270.5 Hz, CF3), 123.0, 128.9 (2 d, 4 CH, Tol), 130.5 (q, 2JC-F = 40.1 Hz, C-4),
134.9, 138.9 (2 s, 2 i-C, Tol) ppm; 19F NMR (CDCl3, 188 MHz): = –64.06 (s, CF3) ppm; IR (KBr): = 3120–
10