7844
A. Kudelko et al. / Tetrahedron 67 (2011) 7838e7845
8.1 Hz, ArCH2eC5: H-200, H-600), 7.29 (1H, s, HeN4), 7.35e7.40 (3H,
m, PheC3: H-30, H-40, H-50), 7.62 (2H, d, J 6.9 Hz, PheC3: H-20, H-60),
9.14 (1H, s, OH), 10.28 (1H, s, HeN1); dC (DMSO-d6) 38.3, 54.9, 115.5,
126.6, 127.2, 128.8, 130.2, 131.5, 133.4, 144.8, 156.6, 163.1; m/z (EI)
281 (Mþ, 14), 206 (22), 77 (53), 72 (26), 63 (15), 59 (32), 55 (18), 44
(45), 73 (64), 44 (35%); lmax (MeOH) 204.4 nm
28.77 cmꢀ1 ꢀ1), 222.8 (18.62), 290.0 (8.27), 296.8 (8.08); nmax
(ATR) 3212, 3065, 1659, 1575, 1525, 1488, 1393, 1347, 1247, 1179,
1069, 1044, 1002, 925, 827, 803, 773, 724, 691 cmꢀ1
(
3
M
.
(100), 43 (17%); lmax (MeOH) 204.4 nm (
3
M
ꢀ1),
4.4.11. 2-(1-Amino-1-(m-nitrophenyl)methyl)-5-phenyl-1,3,4-
226.0 (18.28), 286.2 (5.59), 303.6 (5.62); nmax (ATR) 3224, 1652,
oxadiazole (6i). This compound was obtained as a yellow solid in
1612, 1574, 1514, 1435, 1402, 1319, 1235, 1172, 1103, 1067, 1048, 1016,
31% yield; mp 97e99 ꢁC; ½a D20
ꢀ1.5 (MeOH, c 1); Rf (benzene/AcOEt,
ꢂ
866, 815, 772, 722, 693 cmꢀ1
.
1:3 v/v) 0.13; [Found: C, 60.72; H, 4.07; N, 18.93. C15H12N4O3 re-
quires C, 60.80; H, 4.09; N, 18.90%]; dH (300 MHz, DMSO-d6, Me4Si)
2.06 (2H, br s, NH2), 6.24 (1H, s, CeH), 7.36e7.53 (3H, m, PheC5: H-
30, H-40, H-50), 7.92 (1H, t, J 7.8 Hz, Ph: H-500), 8.08 (2H, d, J 7.8 Hz,
PheC5: H-20, H-60), 8.22 (2H, d, J 7.8 Hz, Ph: H-400, H-600), 8.36 (1H, s,
Ph: H-200); dC (DMSO-d6) 48.5, 122.6, 127.5, 128.7, 128.9, 129.2, 129.4,
129.9, 137.2, 143.3, 154.1, 164.1, 168.0; m/z (EI) 296 (Mþ, 25), 206
(46), 146 (35), 105 (26), 104 (25), 103 (31), 91 (23), 77 (100), 44
4.4.7. 5-(5-Imidazoylmethyl)-3-phenyl-1,2,4-triazin-6-one (5f). This
compound was obtained as a yellow solid in 62% yield; mp
191e192 ꢁC; ½a 2D0
ꢀ2.5 (MeOH, c 5); Rf (benzene/AcOEt, 1:3 v/v)
ꢂ
0.34; [Found: C, 61.09; H, 5.12; N, 27.37. C13H13N5O requires C, 61.16;
H, 5.14; N, 27.42%]; dH (300 MHz, DMSO-d6, Me4Si) 2.84 (2H, m,
CH2eC5), 4.04 (1H, m, CHeC5), 6.68e6.80 (3H, m, PheC3: H-30, H-
40, H-50), 6.96 (1H, s, H-N4), 7.52 (2H, d, J 6.9 Hz, PheC3: H-20, H-60),
8.47 (1H, s, ArCH2eC5: H-400), 8.53 (1H, s, ArCH2eC5: H-200), 10.05
(1H, s, HeN1); dC (DMSO-d6) 37.5, 53.1, 119.2, 127.5, 129.6, 129.6,
131.4, 135.5, 143.5, 152.4, 163.3; m/z (EI) 255 (Mþ, 12), 229 (31), 215
(13), 150 (45), 77 (68), 72 (37), 63 (13), 44 (100). lmax (MeOH):
(58%); lmax (MeOH) 204.6 nm (
(18.90); nmax (ATR) 2924, 1678, 1605, 1528, 1471, 1446, 1405, 1348,
1177, 1073, 1028, 922, 804, 771, 692 cmꢀ1
3
M
ꢀ1), 250.0
.
4.5. X-ray crystal structure analysis for 6h
208.4 nm (
nmax (ATR) 3184, 3020,1656,1610,1552,1413,1175,1104,1068,1044,
945, 859, 817, 772, 694 cmꢀ1
3
M
ꢀ1), 213.4 (12.57), 244.2 (29.55%);
The single crystal of 2-(1-amino-1,1-diphenylmethyl)-5-phenyl-
1,3,4-oxadiazole 6h were used for data collection at 293 (2)K on
a four-circle Oxford Diffraction Xcalibur diffractometer equipped
.
4.4.8. 4-Phenyl-6,7,8,8a-tetrahydropyrrolo[1,2-d][1,2,4]triazin-
with
chromatised Mo K
a two-dimensional CCD detector with graphite mono-
1(2H)-one (5g). This compound was obtained as a yellow solid in
ꢁ
a
radiation (
l¼0.71073 A) and the
u-scan tech-
75% yield; mp 145e147 ꢁC; ½a D20
þ1.8 (MeOH, c 5); Rf (benzene/
ꢂ
nique. Integration of the intensities and correction for Lorenz and
polarisation effects were performed using CrysAlis RED software.44
Crystal structures were solved by direct methods and refined by
a full-matrix least-squares method on F2 using the program
SHELXL-97.45
AcOEt, 1:3 v/v) 0.38; [Found: C, 66.88; H, 6.05; N, 19.47. C12H13N3O
requires C, 66.95; H, 6.10; N, 19.51%]; dH (300 MHz, DMSO-d6,
Me4Si) 1.60 (1H, m, HeC7), 1.80 (1H, m, HeC7), 2.19 (2H, m, HeC8),
3.21 (1H, m, HeC6), 3.51 (1H, m, HeC6), 3.93 (1H, t, J 6.9 Hz,
HeC8a), 7.40e7.44 (3H, m, PheC4: H-30, H-40, H-50), 7.58 (2H, d, J
6.9 Hz, PheC4: H-20, H-60), 10.57 (1H, s, HeN2); dC (DMSO-d6) 23.6,
28.6, 50.89, 55.8, 128.2, 128.3, 129.8, 133.5, 147.7, 163.3; m/z (EI) 215
(Mþ, 91), 186 (25), 159 (23), 158 (100), 145 (12), 118 (8), 104 (21), 91
Empirical formula C21H17N3O, formula weight 327.38, crystal
size 0.16ꢃ0.17ꢃ0.20 mm, crystal system orthorhombic, space group
ꢁ
ꢁ
Pbca (No. 61), unit cell dimensions: a¼9.3893(2) A, b¼14.7810(3) A,
3
ꢁ
ꢁ
c¼24.8854(4) A, V¼3453.68(12) A , Z¼8, calculated density
(9), 77 (13), 68 (14), 51 (5), 41 (10%); lmax (MeOH) 204.4 nm (
ꢃ10ꢀ3
1.259 Mg/m3, absorption coefficient 0.080 mmꢀ1, F(000)¼1376,
q
range for data collection: 3.05e25.00ꢁ, limiting indices: ꢀ11ꢅhꢅ10,
ꢀ17ꢅkꢅ17, ꢀ29ꢅlꢅ29, reflections collected/unique: 20345/3035
[Rint¼0.0236], data/parameters: 3035/233, goodness-of-fit on F2
2885, 1658, 1608, 1463, 1421, 1328, 1285, 1223, 1178, 1156, 1108,
1066, 1050, 1025, 927, 892, 819, 772, 728, 699, 688 cmꢀ1
.
1.067, final R indices [I>2
s
(I)]: R1¼0.0314, wR2¼0.0865, R indices
4.4.9. 2-(1-Amino-1,1-diphenylmethyl)-5-phenyl-1,3,4-oxadiazole
(6h). This compound was obtained as a white solid in 85% yield;
mp 140e141 ꢁC; Rf (benzene/AcOEt, 1:3 v/v) 0.34; [Found: C, 76.98;
H, 5.20; N, 12.80. C21H17N3O requires C, 77.04; H, 5.24; N, 12.83%];
dH (300 MHz, CDCl3, Me4Si) 2.62 (2H, br s, NH2), 7.30e7.51 (13H, m,
(Ph)2eCeC2, PheC5: H-30, H-40, H-50), 7.99 (2H, d, J 8.1 Hz, PheC5:
H-20, H-60); dC (CDCl3) 62.9, 126.9, 127.2, 127.9, 128.3, 128.4, 128.9,
131.7, 143.5, 165.6, 170.7; m/z (EI) 327 (Mþ, 26), 194 (100), 180 (25),
165 (10), 118 (85), 103 (11), 91 (13), 77 (42), 51 (14), 44 (17%); lmax
(all data): R1¼0.0389, wR2¼0.0895, largest diff. peak and hole: 0.150
and ꢀ0.127 eAꢀ3. The H atoms were positioned geometrically and
treated as riding on their parent atoms, with CeH distances of
ꢁ
0.930 A (aromatic). The amino H-atoms coordinate parameters are
refined only.
Complete crystallographic details for 6h are available as Sup-
plementary data (CCDC 827086) and have been deposited at the
Cambridge Crystallographic Data Centre (CCDC), 12 Union Road,
should quote the full literature citation.
(MeOH) 206.0 nm (
3
M
ꢀ1), 253.2 (25.56); nmax
(ATR) 3369, 3293, 1604, 1558, 1546, 1490, 1449, 1361, 1196, 1184,
1168, 1098, 1086, 1067, 1028, 1013, 961, 949, 928, 862, 776, 755, 730,
701, 685 cmꢀ1
.
Acknowledgements
4.4.10. 5-(m-Nitrophenyl)-3-phenyl-1,2,4-triazin-6-one
(5i). This
This work was supported by the State Committee of Scientific
Research, Grant No 0167/B/H03/2010/38.
compound was obtained as a yellow solid in 45% yield; mp
190e192 ꢁC; ½a 2D0
ꢀ3.0 (MeOH, c 1); Rf (benzene/AcOEt, 1:3 v/v)
ꢂ
0.45; [Found: C, 60.75; H, 4.11; N, 18.83. C15H12N4O3 requires C,
60.80; H, 4.09; N, 18.90%]; dH (300 MHz, DMSO-d6, Me4Si) 5.31 (1H,
d, J 2.1 Hz, HeC5), 7.43e7.46 (3H, m, PheC3: H-30, H-40, H-50), 7.69
(1H, t, J 7.8 Hz, PheC5: H-500), 7.78e7.83 (3H, m, PheC5: H-600,
PheC3: H-20, H-60), 8.17e8.20 (3H, m, PheC5: H-200, H-400, HeN4),
10.80 (1H, s, HeN1); dC (DMSO-d6) 56.2, 122.0, 123.6, 126.7, 129.2,
130.7, 131.0, 132.7, 133.9, 143.1, 145.0, 148.5, 161.4; m/z (EI) 296 (Mþ,
12), 281 (38), 221 (100), 207 (54), 161 (36), 159 (52), 146 (24), 77
References and notes
ꢀ
1. Suwinski, J.; Szczepankiewicz, W. In Comprehensive Heterocyclic Chemistry III;
Katritzky, A. R., Ramsden, C. A., Scriven, E. F. V., Taylor, R. J. K., Eds.; Elsevier
Science: Oxford, 2008; Vol. 5, p 398.
2. Amir, M.; Shikha, K. Eur. J. Med. Chem. 2004, 39, 535.
3. Rajapakse, H. A.; Zhu, H.; Young, M. B.; Mott, B. T. Tetrahedron Lett. 2006, 47,
4827.