D.R. Garud et al. / Tetrahedron 65 (2009) 4775–4780
4779
(
77Se–13C)¼55.6 Hz), 35.4, 128.1, 130.1, 138.9, 138.7, 167.2, 203.3.
(2H, s, N–CH2), 7.30–7.35 (5H, m, Ar–H). 13C NMR (100 MHz, CDCl3):
77Se NMR (95 MHz, CDCl3):
d
577.2, 1197.5. MS (EI): m/z¼333 [Mþ].
d
21.3 (1J (77Se–13C)¼63.3 Hz), 35.7, 52.5, 127.6, 128.0, 128.4 135.9,
Anal. Calcd for C11H11NOSe2: C, 39.90; H, 3.35; N, 4.23. Found: C,
39.68; H, 3.43; N, 4.19.
166.8, 203.8. 77Se NMR (75 MHz, CDCl3):
d 574.7, 1109.3. MS (EI):
m/z¼333 [Mþ]. Anal. Calcd for C11H11NOSe2: C, 39.90; H, 3.35; N,
4.23. Found: C, 39.85; H, 3.42; N, 4.25.
4.2.3.1. 4c: X-ray crystallographic data13. Single-crystal X-ray dif-
fraction: Rigaku AFC7R Mercury CCD area-detector diffractometer
4.2.8. 3-Cyclohexyl-2-selenoxoperhydro-1,3-selenazin-4-one (4h)
using graphite monochromated Mo K
a
radiation (l¼0.71069 Å).
Orange crystals. Mp 87–89 ꢀC. IR (KBr): 2929, 1723, 1523, 1297,
The structures were solved by direct methods (SIR97, Altomare, A.,
Burla, M., Camalli, M., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Moliterni, A., Polidori, G., Spagna, R. J. Appl. Crystallogr. 1999, 32,
115) and refined by full-matrix least-squares on F2 (SHELEX-97,
Program for Crystal Structure Refinement, G. M. Sheldrick, Uni-
versitat Go¨ttingen, 1997). All non-hydrogen atoms were refined
anisotropically and hydrogen atoms were refined by a riding
model. Empirical absorption corrections were applied. Single
crystal was grown from Et2O–hexane: C11H11NOSe2, Mr¼331.13,
Red color crystal (0.29ꢃ0.20ꢃ0.10 mm3), Crystal system: trigonal,
space group: ‘P32’, a¼11.4194(9), b¼11.4194(9), c¼7.7246(8) Å,
1220, 1127 cmꢁ1 1H NMR (400 MHz, CDCl3):
. d 1.15–1.45 (4H, m,
cyclohexyl), 1.60–1.90 (4H, m, cyclohexyl), 2.21–2.34 (2H, m,
cyclohexyl), 2.96 (2H, t, J¼6.9 Hz, 2J (77Se–1H)¼28.0 Hz, Se–CH2),
3.36 (2H, t, J¼6.9 Hz, O]C–CH2), 5.70 (1H, tt, J¼3.2, 11.9 Hz,
cyclohexyl). 13C NMR (100 MHz, CDCl3):
d
22.3 (1J
(
77Se–13C)¼63.3 Hz), 25.2, 26.3, 29.3, 37.7, 66.4, 167.1, 205.4. 77Se
NMR (75 MHz, CDCl3):
d
576.3, 1051.3. MS (EI): m/z¼325 [Mþ]. Anal.
Calcd for C10H15NOSe2: C, 37.17; H, 4.68; N, 4.33. Found: C, 37.28; H,
5.03; N, 4.22.
4.2.9. 3,6-Diphenyl-2-selenoxoperhydro-1,3-selenazin-4-one (4i)
g
¼120ꢀ, V¼872.35(13) Å3, Z¼3,
m
¼6.330 mmꢁ1, Dcalcd¼1.891 Mg/
Purple crystals. Mp 195–196 ꢀC. IR (KBr): 1706, 1591, 1231, 1209,
m3, Reflections collected: 7120, independent reflections: 2104
1194, 1121 cmꢁ1 1H NMR (600 MHz, CDCl3):
. d 3.77–3.90 (2H, m,
unique (Rint¼0.0431), 183 parameters,
q
range for data collection
O]C–CH2), 4.90 (1H, dd, J¼3.4, 12.2 Hz, Se–CH), 7.19 (2H, d,
J¼7.6 Hz, Ar–H), 7.33–7.39 (3H, m, Ar–H), 7.41 (2H, d, J¼7.6 Hz, Ar–
H), 7.45 (1H, t, J¼7.6 Hz, Ar–H), 7.49 (2H, t, J¼7.6 Hz, Ar–H). 13C NMR
3.35–27.49ꢀ. Limiting indices –14h14, –14k14, –7l10, largest max./
min. in the final difference Fourier synthesis 0.312 e Åꢁ3
/
ꢁ0.247 e Åꢁ3, max./min. transmission 0.5702/0.2611, T¼296(2) K,
(150 MHz, CDCl3):
d
41.8 (1J (77Se–13C)¼60.7 Hz), 42.3, 127.3, 128.4,
R1¼0.0293 [I>2
s
(I)], wR2¼0.0595. R indices (all data) R1¼0.0323,
128.8, 128.9, 129.4, 129.6, 136.2, 141.0, 167.9, 203.6. 77Se NMR
wR2¼0.0607.
(95 MHz, CDCl3):
Calcd for C16H13NOSe2: C, 48.87; H, 3.33; N, 3.56. Found: C, 48.52; H,
3.47; N, 3.54.
d
678.9, 1186.0. MS (EI): m/z¼395 [Mþ]. Anal.
4.2.4. 3-(o-Chlorophenyl)-2-selenoxoperhydro-1,3-
selenazin-4-one (4d)
Red oil. IR (neat): 1716, 1473, 1234, 1129 cmꢁ1
.
1H NMR
4.2.10. 6-(p-Nitrophenyl)-3-phenyl-2-selenoxoperhydro-1,3-
selenazin-4-one (4j)
(400 MHz, CDCl3):
d
3.18 (2H, td, J¼2.3, 6.4 Hz, 2J
(
77Se–1H)¼29.8 Hz, Se]CH2), 3.55 (2H, t, J¼6.4 Hz, O]C–CH2),
Purple crystals. Mp 202–203 ꢀC. IR (KBr): 1706, 1598, 1522, 1349,
7.23–7.27 (1H, m, Ar), 7.35–738 (2H, m, Ar), 7.50 (1H, m, Ar). 13C
1236, 1198, 1114 cmꢁ1. 1H NMR (600 MHz, CDCl3):
d 3.82–3.92 (2H,
NMR (100 MHz, CDCl3):
d
21.8 (1J (77Se–13C)¼60.4 Hz), 35.3, 127.9,
m, O]C–CH2), 4.98 (1H, dd, J¼4.0, 11.0 Hz, 2J (77Se–1H)¼24.8 Hz,
Se–CH), 7.18 (2H, d, J¼8.2 Hz, Ar–H), 7.44–7.52 (3H, m, Ar–H), 7.56
(2H, d, J¼8.2 Hz, Ar–H), 8.29 (2H, d, J¼8.2 Hz, Ar–H). 13C NMR
130.3, 130.4, 130.6, 132.1, 138.7, 166.7, 202.0. 77Se NMR (75 MHz,
CDCl3):
d
581.1, 1206.2. MS (EI): m/z¼353 [Mþ], 318 [MþꢁCl]. Anal.
Calcd for C10H8ClNOSe2: C, 34.17; H, 2.29; N, 3.98. Found: C, 33.99;
H, 2.42; N, 3.98.
(150 MHz, CDCl3):
d
40.9 (1J (77Se–13C)¼63.6 Hz), 41.6, 124.7, 128.3,
128.6, 129.1, 129.6, 140.5, 143.7, 147.9, 166.9, 201.4. 77Se NMR
(95 MHz, CDCl3):
Calcd for C16H12N2O3Se2: C, 43.85; H, 2.76; N, 6.39. Found: C, 43.91;
H, 3.09; N, 6.40.
d
675.0, 1216.7. MS (EI): m/z¼440 [Mþ]. Anal.
4.2.5. 3-(o-Tolyl)-2-selenoxoperhydro-1,3-selenazin-4-one (4e)
Red crystals. Mp 115–116 ꢀC. IR (KBr): 1712, 1234, 1130 cmꢁ1. 1H
NMR (400 MHz, CDCl3):
d 2.12 (3H, s, Ar–CH3), 3.09–3.23 (2H, m,
Se–CH2), 3.48–3.62 (2H, m, O]C–CH2), 7.06 (1H, d, J¼7.8 Hz, Ar–H),
4.2.11. 6-Cyclohexyl-3-phenyl-2-selenoxoperhydro-1,3-selenazin-
7.25–7.36 (3H, m, Ar–H). 13C NMR (100 MHz, CDCl3):
d
17.6, 21.7 (1J
4-one (4k)
(
77Se–13C)¼56.6 Hz), 35.5, 127.3, 128.4, 129.3, 131.2, 135.4, 140.2,
Pink crystals. Mp 205–207 ꢀC. IR (KBr): 1705, 1222, 1132 cmꢁ1
.
167.0, 202.0. 77Se NMR (75 MHz, CDCl3):
d
574.6, 1195.8. MS (EI):
1H NMR (400 MHz, CDCl3):
d 1.03–1.31 (5H, m, cyclohexyl), 1.68–
m/z¼333 [Mþ]. Anal. Calcd for C11H11NOSe2: C, 39.90; H, 3.35; N,
1.92 (6H, m, cyclohexyl), 3.40–3.48 (5H, m, cyclohexyl), 3.40–3.48
(2H, m, O]C–CH2), 3.57–3.62 (1H, m, Se–CH2), 7.13 (2H, d,
J¼6.8 Hz, Ar–H), 7.40–7.49 (3H, m, Ar–H). 13C NMR (100 MHz,
4.23. Found: C, 40.24; H, 3.47; N, 4.09.
4.2.6. 3-(2-Naphtyl)-2-selenoxoperhydro-1,3-selenazin-4-one (4f)
CDCl3):
d
25.9, 26.0, 30.8, 39.8, 41.8 (1J (77Se–13C)¼60.4 Hz), 45.9,
Red crystals. Mp 187–188 ꢀC. IR (KBr): 1714, 1653, 1598, 1508,
128.6, 128.9, 129.5, 141.3, 168.4, 202.5. 77Se NMR (75 MHz, CDCl3):
1234, 1128 cmꢁ1
.
1H NMR (600 MHz, CDCl3):
d
3.07–3.27 (2H, m,
d
631.3, 1181.4. MS (EI): m/z¼401 [Mþ]. Anal. Calcd for C11H11NOSe2:
Se–CH2), 3.52–3.65 (2H, m, O]C–CH2), 7.24 (1H, dd, J¼1.9, 6.4 Hz,
C, 48.13; H, 4.80; N, 3.51. Found: C, 48.32; H, 5.03; N, 3.24.
Ar–H), 7.46–7.55 (2H, m, Ar–H), 7.66 (1H, d, J¼1.9 Hz, Ar–H), 7.81–
7.94 (3H, m, Ar–H). 13C NMR (150 MHz, CDCl3):
d
21.7 (1J
4.2.12. 5,6-Dimethyl-3-phenyl-2-selenoxoperhydro-1,3-selenazin-
4-one (4l)
(
77Se–13C)¼63.3 Hz), 35.4, 126.1, 126.5, 126.9, 127.3, 127.9, 128.2,
129.2, 133.0, 133.5, 138.4, 167.3, 203.1. 77Se NMR (95 MHz, CDCl3):
Red crystals. Mp 138–139 ꢀC. IR (KBr): 1719, 1587, 1305, 1211,
d
580.3, 1213.0. MS (EI): m/z¼369 [Mþ]. Anal. Calcd for
1124 cmꢁ1. 1H NMR (600 MHz, CDCl3):
d
1.53 (3H, d, J¼6.9 Hz, CH3),
C14H11NOSe2: C, 45.80; H, 3.02; N, 3.81. Found: C, 45.72; H, 3.14; N,
3.76.
1.67 (3H, d, J¼6.9 Hz, CH3), 3.25 (1H, quin., J¼6.9 Hz, O]C–CH), 3.33
(1H, quin., J¼6.9 Hz, 2J (77Se–1H)¼46.7 Hz, Se–CH), 7.12 (2H, d,
J¼8.3 Hz, Ar–H), 7.40–7.48 (3H, m, Ar–H). 13C NMR (150 MHz,
4.2.7. 3-Benzyl-2-selenoxoperhydro-1,3-selenazin-4-one (4g)
CDCl3):
d
15.7, 20.4, 40.2 (1J (77Se–13C)¼62.1 Hz), 46.1, 128.5, 128.7,
Red crystals. Mp 108–109 ꢀC. IR (KBr): 1714, 1603, 1341, 1324,
129.3, 141.7, 170.5, 202.1. 77Se NMR (95 MHz, CDCl3):
d 627.4, 1167.1.
1133 cmꢁ1
(
.
1H NMR (400 MHz, CDCl3):
d
2.98 (2H, t, J¼6.9 Hz, 2J
MS (EI): m/z¼347 [Mþ]. Anal. Calcd for C12H13NOSe2: C, 41.76; H,
77Se–1H)¼28.0 Hz, Se–CH2), 3.41 (2H, t, J¼6.9 Hz, O]C–CH2), 5.85
3.80; N, 4.06. Found: C, 41.68; H, 3.94; N, 4.05.