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Helvetica Chimica Acta – Vol. 89 (2006)
Crystals suitable for the X-ray crystal-structure determination were grown from CHCl3/MeOH by
slow evaporation of the solvent.
(4-Bromophenyl)-(3,6-dihydro-5-phenyl-2H-[1,3,4]selenadiazin-2-yliden)amine (3b). Yield: 267.3
mg (68%). Yellowish crystals. M.p. 179–1818 (AcOEt). IR: 3443m (br.), 3133w, 3056w, 2917m (br.),
1623m, 1587vs, 1567s, 1490m, 1472m, 1444m, 1403m, 1297w, 1276w, 1214s, 1173m, 1105w, 1072m,
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1003w, 889m, 841m, 827s, 759s, 693s, 658m, 632w. H-NMR: 3.93 (s, CH2); 6.70–7.00 (br. m, 2 arom.
H); 7.45–7.60 (m, 5 arom. H); 7.85–8.00 (m, 2 arom. H); 11.71 (br. s, NH). 13C-NMR: 15.3 (t, CH2);
121.6 (s, 1 arom. C); 126.2 (d, 2 arom. CH); 128.5 (d, 3 arom. CH); 129.3 (d, 2 arom. CH); 131.3 (d, 2
arom. CH); 135.3, 148.0, 154.3 (3s, 2 arom. C, C(5)); 166.2 (s, C(2)). CI-MS: 398 (13), 397 (14), 396
(77), 395 (21), 394 (100, [M(80Se,79Br)+1]+), 393 (21), 392 (47), 391 (14), 390 (14). Anal. calc. for
C15H12BrN3Se (393.15): C 45.83, H 3.08, N 10.69; found: C 45.46, H 3.21, N 10.42.
(4-Chlorophenyl)-(3,6-dihydro-5-phenyl-2H-[1,3,4]selenadiazin-2-yliden)amine (3c). Yield: 191.8
mg (55%). Yellowish crystals. M.p. 178–1808 (AcOEt). IR: 3444m (br.), 3125w, 3047w, 2908m (br.),
2866m (br.), 1623m, 1584vs, 1568s, 1491s, 1473m, 1444w, 1403m, 1297w, 1277w, 1214s, 1178w, 1172m,
1107w, 1093m, 1071w, 1003w, 888m, 843w, 830m, 796w, 760m, 694m, 683w, 662w. 1H-NMR: 3.95 (s,
CH2); 6.80–7.05 (br. m, 2 arom. H); 7.45 (d-like, J=8.4, 2 arom. H); 7.50–7.60 (m, 3 arom. H);
7.90–8.05 (m, 2 arom. H); 11.64 (br. s, NH). 13C-NMR: 15.3 (t, CH2); 126.2 (d, 2 arom. CH); 128.4 (d,
2 arom. CH); 128.5 (d, 3 arom. CH); 129.3 (s, 2 arom. CH); 135.0, 135.3, 147.5, 155.3 (4s, 3 arom. C,
C(5)); 163.9 (s, C(2)). CI-MS: 354 (6), 353 (8), 352 (44), 351 (18), 350 (100, [M(80Se,35Cl)+1]+), 349
(15), 348 (48), 347 (17), 346 (17). Anal. calc. for C15H12ClN3Se (348.69): C 51.67, H 3.47, N 12.05;
found: C 51.51, H 3.74, N 11.73.
(3,6-Dihydro-5-phenyl-2H-[1,3,4]selenadiazin-2-ylidene)(4-methoxyphenyl)amine (3d). Yield: 229.3
mg (67%). Yellowish crystals. M.p. 132–1348 (AcOEt). IR: 3439m (br.), 3346m, 2912m (br.), 2836w,
1654s, 1638m, 1580vs, 1544s, 1509vs, 1447w, 1282m, 1249s, 1211w, 1178w, 1109w, 1077w, 1033w, 1011w,
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892w, 826m, 800w, 757w, 713m, 692w. H-NMR: 3.82 (s, MeO); 3.90 (s, CH2); 6.90–7.20 (br. m, d-like
at 6.92, J=8.2, 4 arom. H); 7.30–7.55 (m, 2 arom. H); 7.75–8.00 (m, 2 arom. H); 11.82 (br. s, NH).
13C-NMR: 15.1 (t, CH2); 55.4 (q, MeO); 115.6 (d, 2 arom. CH); 124.2 (d, 2 arom. CH); 128.3 (d, 2
arom. CH); 129.2 (d, 2 arom. CH); 131.1 (d, 1 arom. CH); 133.9, 147.8, 153.7, 158.4 (4s, 3 arom. C,
C(5)); 166.1 (s, C(2)). CI-MS: 350 (8), 349 (12), 348 (65), 347 (21), 346 (100, [M(80Se)+1]+), 345 (19),
344 (52), 343 (15), 342 (14). Anal. calc. for C16H15N3OSe (344.28): C 55.82, H 4.39, N 12.21; found: C
55.95, H 4.67, N 12.23.
(4-Bromophenyl)[5-(4-bromophenyl)-3,6-dihydro-2H-[1,3,4]selenadiazin-2-yliden]amine
(3e).
Yield: 377.6 mg (80%). Yellowish crystals. M.p. 176–1788 (AcOEt). IR: 3442m (br.), 3155w, 3051w,
2920m (br.), 1626m, 1590vs, 1576s, 1554m, 1485m, 1407w, 1299w, 1271w, 1209m, 1172m, 1146w, 1101w,
1070m, 1000m, 890w, 828m, 725w, 707w, 653w, 604w. 1H-NMR: 3.88 (s, CH2); 6.85–7.10 (br. m, 2
arom. H); 7.68 (d-like, J=8.2, 2 arom. H); 7.80 (d-like, J=8.2, 2 arom. H); 7.90–8.00 (m, 2 arom. H);
11.79 (br. s, NH). 13C-NMR: 15.0 (t, CH2); 122.8 (s, 2 arom. C); 124.2 (d, 2 arom. CH); 128.1 (d, 2
arom. CH); 131.3 (d, 2 arom. CH); 131.5 (d, 2 arom. CH); 134.5, 147.2, 155.5 (3s, 2 arom. C, C(5));
162.9 (s, C(2)). CI-MS: 478 (7), 477 (9), 476 (52), 475 (19), 474 (100, [M(80Se,81Br,79Br)+1]+), 473 (23),
472 (85, [M(80Se,79Br,79Br)+1]+), 471 (19), 470 (35), 469 (8), 468 (9). Anal. calc. for C15H11Br2N3Se
(472.05): C 38.17, H 2.35, N 8.90; found: C 38.01, H 2.54, N 8.60.
[5-(4-Bromophenyl)-3,6-dihydro-2H-[1,3,4]selenadiazin-2-ylidene](4-methylphenyl)amine
(3f).
Yield: 317.5 mg (78%). Yellowish crystals. M.p. 202–2048 (AcOEt). IR: 3441m (br.), 2919m, 2853m
(br.), 1623m, 1583vs, 1554m, 1508w, 1486w, 1406w, 1269w, 1221m, 1173m, 1075m, 999w, 890w, 826m.
1H-NMR: 2.40 (s, Me); 3.93 (s, CH2); 6.90–7.20 (m, 2 arom. H); 7.24 (d-like, J=8.1, 2 arom. H); 7.52
(d-like, J=8.1, 2 arom. H); 7.66 (d-like, J=8.1, 2 arom. H); 11.50 (br. s, NH). 13C-NMR: 14.8 (t, CH2);
20.3 (q, Me); 121.6 (s, 1 arom. C); 122.6 (d, 2 arom. CH); 128.0 (d, 2 arom. CH); 129.0 (d, 2 arom.
CH); 131.4 (d, 2 arom. CH); 134.7, 145.6, 155.0 (3s, 3 arom. C, C(5)); 163.2 (C(2)). CI-MS: 412 (13),
411 (15), 410 (77), 409 (33), 408 (100, [M(80Se,79Br)+1]+), 407 (40), 406 (50), 405 (23), 404 (17). Anal.
calc. for C16H14BrN3Se (407.07): C 47.20, H 3.47, N 10.32; found: C 46.72, H 3.51, N 10.15.