January 2011 Synthesis and Crystal Structure of Novel [1,2,4]Oxadiazolo[5,4-d][1,5]benzothiozepine
Derivatives Containing Pyrazole Moiety
111
Jbx ¼ 12.8 Hz), 2.93–2.86 (dd, 1H, H4a, Jax ¼ 4.8 Hz, Jab
¼
6.70 (m, 24H, Ar-H), 4.65–4.62 (dd, 1H, H5x, Jax ¼ 4.8 Hz,
Jbx ¼ 12.4 Hz), 3.16–3.12 (dd, 1H, H4a, Jax ¼ 4.8 Hz, Jab
¼
13.6 Hz), 2.69–2.60 (dd, 1H, H4b, Jbx ¼ 12.8 Hz, Jab ¼ 13.6
Hz), 2.05(s, 3H, ACH3); MS(EI)m/z(%): 606(Mþ), 513, 394,
330, 287, 226, 211, 105(100), 77.
13.6 Hz), 3.05–3.01 (dd, 1H, H4b, Jbx ¼ 12.4 Hz, Jab ¼ 13.6
Hz), 2.66 (s, 3H, ACH3); MS(EI)m/z(%): 622(Mþ), 513, 394,
330, 287, 226, 211, 105(100), 77.
3a,4,5,11-Tetrahydro-1-(4-chlorophenyl)-3a-phenyl-5-(3-methyl-
1-phenyl-5-phenylthio-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo[5,4-d][1,5]
benzothiazepine(40b). This compound was obtained as pale yel-
3a,4,5,11-Tetrahydro-1-(4-methoxyphenyl)-3a-phenyl-5-(3-
methyl-1-phenyl-5-phenyloxyl-1H-pyrazol-4-yl)-[1,2,4]oxadia-
zolo[5,4-d][1,5]benzothiazepine(4b). This
compound was
obtained as white crystals. IR(KBr)t/cmꢀ1: 3055 (Ar-H),
1633, 1560 (C¼¼N), 752 (CASAC); 1H NMR(CDCl3, 400
MHz) d: 7.78–6.54 (m, 23H, Ar-H), 3.79 (s, 3H, AOCH3),
3.44–3.39 (dd, 1H, H5x, Jax ¼ 4.4 Hz, Jbx ¼ 12.4 Hz), 2.89–
2.85 (dd, 1H, H4a, Jax ¼ 4.4 Hz, Jab ¼ 14.8 Hz), 2.65–2.60
(dd, 1H, H4b, Jbx ¼ 12.4Hz, Jab ¼ 14.8 Hz), 2.06 (s, 3H,
ACH3); MS(EI)m/z(%): 636(Mþ), 543, 394, 360, 287, 256,
211, 105(100), 77.
low crystals. IR(KBr)t/cmꢀ1
: 3058 (Ar-H), 1637, 1561
1
(C¼¼N), 757 (CASAC); H NMR(CDCl3, 400 MHz) d: 7.92–
6.69 (m, 23H, Ar-H), 4.64–4.60 (dd, 1H, H5x, Jax ¼ 5.2 Hz,
Jbx ¼ 12.4 Hz), 3.16–3.10 (dd, 1H, H4a, Jax ¼ 5.2 Hz, Jab
¼
14.0 Hz), 3.03–2.98 (dd, 1H, H4b, Jbx ¼ 12.4 Hz, Jab ¼ 14.0
Hz), 2.65 (s, 3H, ACH3); MS(EI)m/z(%): 656(Mþ), 547, 394,
364, 287, 260, 211, 105(100), 77.
3a,4,5,11-Tetrahydro-1-(4-methoxyphenyl)-3a-phenyl-5-(3-
methyl-1-phenyl-5-phenylthio-1H-pyrazol-4-yl)-[1,2,4]oxadia-
zolo[5,4-d][1,5]benzothiazepine(40c). This compound was
obtained as white crystals. IR(KBr)t/cmꢀ1: 3058 (Ar-H),
1641, 1562 (C¼¼N), 759 (CASAC); 1H NMR(CDCl3, 400
MHz) d: 7.83–6.65 (m, 23H, Ar-H), 4.64–4.59 (dd, 1H, H5x,
Jax ¼ 5.2 Hz, Jbx ¼ 12.8 Hz), 3.89 (s, 3H, AOCH3), 3.15–
3.10 (dd, 1H, H4a, Jax ¼ 5.2 Hz, Jab ¼ 13.6 Hz), 3.02–2.98
(dd, 1H, H4b, Jbx ¼ 12.8 Hz, Jab ¼ 13.6 Hz), 2.65 (s, 3H,
ACH3); MS(EI)m/z(%): 652(Mþ), 543, 394, 360, 287, 256,
211, 105(100), 77.
3a,4,5,11-Tetrahydro-1-(4-nitrophenyl)-3a-phenyl-5-(3-methyl-
1-phenyl-5-phenylthio-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo[5,4-d][1,5]
benzothiazepine(40d). This compound was obtained as pale yel-
low crystals. IR(KBr)t/cmꢀ1: 3058(Ar-H), 1634, 1559 (C¼¼N),
759 (CASAC); 1H NMR(CDCl3, 400 MHz) d: 8.30–6.64 (m,
23H, Ar-H), 4.71–4.67 (dd, 1H, H5x, Jax ¼ 4.8 Hz, Jbx ¼ 12.4
Hz), 3.24–3.19 (dd, 1H, H4a, Jax ¼ 4.8 Hz, Jab ¼ 13.6 Hz),
3.12–3.08 (dd, 1H, H4b, Jbx ¼ 12.4 Hz, Jab ¼ 13.6 Hz),
2.70(s, 3H, ACH3); MS(EI)m/z(%): 667(Mþ), 558, 394, 375,
287, 271, 211, 105(100), 77.
3a,4,5,11-Tetrahydro-1-phenyl-3a-(4-chlorophenyl)-5-(3-methyl-
1-phenyl-5-phenyloxyl-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo[5,4-d][1,5]
benzothiazepine(4c). This compound was obtained as pale yel-
low crystals. IR(KBr)t/cmꢀ1: 3058(Ar-H), 1635, 1561 (C¼¼N),
749 (CASAC); 1H NMR(CDCl3, 400 MHz) d: 7.41–6.61 (m,
23H, Ar-H), 3.81–3.75 (dd, 1H, H5x, Jax ¼ 5.2 Hz, Jbx ¼ 12.8
Hz), 3.10–3.05(dd, 1H, H4a, Jax ¼ 5.2 Hz, Jab ¼ 13.6 Hz),
3.02–2.96 (dd, 1H, H4b, Jbx ¼ 12.8 Hz, Jab ¼ 13.6 Hz), 2.08
(s, 3H, ACH3); MS(EI)m/z(%):640(Mþ), 547, 431, 364, 321,
245, 226, 139(100), 77.
3a,4,5,11-Tetrahydro-1-(4-methoxyphenyl)-3a-(4-chlorophenyl)-
5-(3-methyl-1-phenyl-5-phenyloxyl-1H-pyrazol-4-yl)-[1,2,4]oxadia-
zolo[5,4-d][1,5]benzothiazepine(4d). This compound was
obtained as white crystals. IR(KBr)t/cmꢀ1: 3061 (Ar-H), 1631,
1557 (C¼¼N), 751 (CASAC); 1H NMR(CDCl3, 400 MHz) d:
7.80–6.58 (m, 22H, Ar-H), 3.82 (s, 3H, AOCH3), 3.35–3.32
(dd, 1H, H5x, Jax ¼ 4.4 Hz, Jbx ¼ 13.2 Hz), 2.83–2.76 (dd, 1H,
H4a, Jax ¼ 4.4 Hz, Jab ¼ 14.0 Hz), 2.63–2.57 (dd, 1H, H4b, Jbx
¼ 13.2 Hz, Jab ¼ 14.0 Hz), 2.10 (s, 3H, ACH3); MS(EI)m/
z(%):670(Mþ), 577, 431, 394, 321, 256, 245, 139(100), 77.
3a,4,5,11-Tetrahydro-1-phenyl-3a-(4-methxoyphenyl)-5-(3-
methyl-1-phenyl-5-phenyloxyl-1H-pyrazol-4-yl)-[1,2,4]oxadia-
3a,4,5,11-Tetrahydro-1-phenyl-3a-(4-chlorophenyl)-5-(3-
methyl-1-phenyl-5-phenylthio-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo
[5,4-d][1,5]benzothiazepine(40e). This compound was obtained
as yellow crystals. IR(KBr)t/cmꢀ1: 3063(Ar-H), 1635, 1561
zolo[5,4-d][1,5]benzothiazepine(4e). This
compound
was
obtained as white crystals. IR(KBr)t/cmꢀ1: 3059 (Ar-H), 1634,
1560 (C¼¼N), 750 (CASAC); 1H NMR(CDCl3, 400 MHz) d:
7.58–6.61 (m, 23H, Ar-H), 3.76 (s, 3H, AOCH3), 3.74–3.68
(dd, 1H, H5x, Jax ¼ 5.2 Hz, Jbx ¼ 12.8 Hz), 3.06–3.02 (dd, 1H,
H4a, Jax ¼ 5.2 Hz, Jab ¼ 13.6 Hz), 3.01–2.94 (dd, 1H, H4b, Jbx
¼ 12.8 Hz, Jab ¼ 13.6 Hz), 2.06(s, 3H, ACH3); MS(EI)m/
z(%):636(Mþ), 543, 427, 360, 317, 241, 226, 135(100), 77.
3a,4,5,11-Tetrahydro-1,3a-di(4-methxoyphenyl)-5-(3-methyl-
1-phenyl-5-phenyloxyl-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo[5,4-d]
[1,5]benzothiazepine(4f). This compound was obtained as
white crystals. IR(KBr)t/cmꢀ1: 3060 (Ar-H), 1632, 1559
1
(C¼¼N), 760 (CASAC); H NMR(CDCl3, 400 MHz) d: 7.84–
6.71 (m, 23H, Ar-H), 4.58–4.55 (dd, 1H, H5x, Jax ¼ 4.4 Hz,
Jbx ¼ 12.4 Hz), 3.08–3.04 (dd, 1H, H4a, Jax ¼ 4.4 Hz, Jab
¼
14.0 Hz), 3.00–2.95 (dd, 1H, H4b, Jbx ¼ 12.4 Hz, Jab ¼ 14.0
Hz), 2.64 (s, 3H, ACH3); MS(EI)m/z(%): 656(Mþ), 547, 431,
364, 321, 245, 226, 139(100), 77.
3a,4,5,11-Tetrahydro-1,3a-di(4-chlorophenyl)-5-(3-methyl-1-
phenyl-5-phenylthio-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo[5,4-d][1,5]
benzothiazepine(40f). This compound was obtained as pale yel-
low crystals. IR(KBr)t/cmꢀ1
: 3061 (Ar-H), 1635, 1560
1
(C¼¼N), 750 (CASAC); H NMR(CDCl3, 400 MHz) d: 7.83–
1
(C¼¼N), 760 (CASAC); H NMR(CDCl3, 400 MHz) d: 7.89–
6.59 (m, 22H, Ar-H), 3.81 (s, 3H, AOCH3), 3.75 (s, 3H,
AOCH3), 3.41–3.24 (dd, 1H, H5x, Jax ¼ 5.2 Hz, Jbx ¼ 12.0
Hz), 2.84–2.77 (dd, 1H, H4a, Jax ¼ 5.2 Hz, Jab ¼ 14.8 Hz),
2.64–2.57 (dd, 1H, H4b, Jbx ¼ 12.0 Hz, Jab ¼ 14.8 Hz), 2.11
(s, 3H, ACH3); MS(EI)m/z(%):666(Mþ), 573, 427, 390, 317,
256, 241, 135(100), 77.
6.65 (m, 22H, Ar-H), 4.59–4.55 (dd, 1H, H5x, Jax ¼ 4.8 Hz,
Jbx ¼ 12.4 Hz), 3.08–3.04 (dd, 1H, H4a, Jax ¼ 4.8 Hz, Jab
¼
14.0 Hz), 3.00–2.95 (dd, 1H, H4b, Jbx ¼ 12.4 Hz, Jab ¼ 14.0
Hz), 2.65 (s, 3H, ACH3); MS(EI)m/z(%): 690(Mþ), 581, 431,
398, 321, 260, 245, 139(100), 77.
3a,4,5,11-Tetrahydro-1-(4-methoxyphenyl)-3a-(4-chloro-
phenyl)-5-(3-methyl-1-phenyl-5-phenylthio-1H-pyrazol-4-yl)-
[1,2,4]oxadiazolo[5,4-d][1,5]benzothiazepine(40g). This com-
pound was obtained as white crystals. IR(KBr)t/cmꢀ1: 3061 (Ar-
3a,4,5,11-Tetrahydro-1,3a-diphenyl-5-(3-methyl-1-phenyl-5-
phenylthio-1H-pyrazol-4-yl)-[1,2,4]oxadiazolo[5,4-d][1,5]
benzothiazepine(40a). This compound was obtained as pale
yellow crystals. IR(KBr)t/cmꢀ1: 3061 (Ar-H), 1631, 1567
1
1
H), 1636, 1560 (C¼¼N), 758 (CASAC); H NMR(CDCl3, 400
(C¼¼N), 753 (CASAC); H NMR(CDCl3, 400 MHz) d: 7.88–
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet