1
12
A. Dandia and A. K. Jain
Vol 50
13
Cl N O : C, 62.64; H, 4.21; N, 11.69. Found: C, 62.78; H, 4.38;
CH), 6.98–8.16 (m, 13H, ArH), 7.33 (s, 2H, NH); C NMR
2
4 2
N, 11.54.
(DMSO-d , 75 MHz): d 19.2, 57.7, 62.9, 114.8, 116.3, 119.7,
6
6
,10-Bis-(4-bromophenyl)-4-methyl-2-phenyl-2,3,7,9-tetra-
120.4, 121.9, 125.8, 130.3, 132.9, 133.1, 136.2 141.3, 169.1,
+
azaspiro[4.5]dec-3-ene-1,8-dione (4d). White crystalline solid;
yield 91%); mp 230–232 C; IR (KBr): n = 3378, 3224, 3092,
720, 1692, 1612 cm
176.8; MS (m/z): 517 (M + H) . Anal. Calcd for C25
H
20
N
6
O
5
ꢀ
(
1
S: C, 58.13; H, 3.90; N, 16.27. Found: C, 58.04; H, 4.07; N,
16.36.
À1
1
;
H NMR (DMSO-d , 300 MHz,
6
mixture-major isomer only): d 2.32 (s, 3H, CH ), 5.08 (s, 2H,
6,10-Bis-(4-fluorophenyl)-4-methyl-2-phenyl-8-thioxo-2,3,7,9-
3
1
3
CH), 6.93–7.54 (m, 13H, ArH), 7.30 (s, 2H, NH); C NMR
DMSO-d , 75 MHz): d 18.7, 58.1, 62.8, 113.9, 114.8, 120.3,
20.7, 125.4, 127.8, 128.9, 129.0, 130.3, 131.8, 136.7, 161.8,
tetraazaspiro[4.5]dec-3-en-1-one (4j).
White crystalline solid;
ꢀ
(
6
(yield 92%); mp 244–246 C; IR (KBr): n = 3372, 3208, 3084,
À1
1
1
1
1718, 1694, 1610 cm
;
H NMR (DMSO-d , 300 MHz,
6
+
71.2; MS (m/z): 569 (M + H) . Anal. Calcd for C H
mixture-major isomer only): d 2.32 (s, 3H, CH ), 5.07 (s, 2H,
25 20
3
1
3
Br
2
N
4
O
2
: C, 52.84; H, 3.55; N, 9.86. Found: C, 52.67; H,
CH), 6.88–7.62 (m, 13H, ArH), 7.33 (s, 2H, NH); C NMR
(DMSO-d , 75 MHz): d 18.7, 57.5, 62.6, 114.1, 116.3, 118.7,
3
.67; N, 10.02.
-Methyl-6,10-bis-(4-nitrophenyl)-2-phenyl-2,3,7,9-tetra-
6
4
120.8, 121.9, 125.8, 127.3, 128.9, 128.1, 129.47, 137.8, 168.4,
+
azaspiro[4.5]dec-3-ene-1,8-dione (4e). White crystalline solid;
176.1; MS (m/z): 463 (M + H) . Anal. Calcd for C H
2
5
20
ꢀ
(
1
yield 87%); mp 246–248 C; IR (KBr): n = 3394, 3218, 3092,
F N OS: C, 64.92; H, 4.36; N, 12.11. Found: C, 64.77; H,
2 4
À1
1
724, 1698, 1624 cm
;
H NMR (DMSO-d
6
, 300 MHz,
4.22; N, 11.92.
mixture-major isomer only): d 2.33 (s, 3H, CH
CH), 6.94–8.12 (m, 13H, ArH), 7.32 (s, 2H, NH); C NMR
DMSO-d , 75 MHz): d 18.9, 58.4, 63.2, 113.5, 114.9,
3
), 5.18 (s, 2H,
7,7-Dimethyl-4-phenyl-4,6,7,8-tetrahydro-1H,3H-quinazoline-
1
3
ꢀ
2,5-dione (7). White solid; (yield 76%); mp 290–292 C; IR
À1
1
(
(KBr): n = 3320, 3258, 2966, 1710, 1680, 1608cm ; H NMR
(DMSO-d , 300 MHz): d 0.97(s, 3H, CH ); 1.10(s, 3H, CH );
6
1
1
19.2, 121.3, 125.7, 127.4, 128.9, 129.0, 131.6, 133.1,
42.2, 161.7, 171.8; MS (m/z): 501 (M + H) . Anal. Calcd
6
3
3
+
2.18 (q, J = 16.1 Hz, 2H, CH2); 2.39 (q, J = 16.8Hz, 2H, CH2 );
for C25
6
6
H
20
N
6
O
6
: C, 60.00; H, 4.03; N, 16.79. Found: C,
0.17; H, 3.97; N, 16.62.
,10-Bis-(4-methoxyphenyl)-4-methyl-2-phenyl-8-thioxo-
5.27 (d, J =2.8 Hz, 1H, CH); 7.32–7.21 (m, 5H, Ar); 7.46 (s, 1H,
NH); 9.39 (s, 1H, NH); C NMR (DMSO-d , 75MHz): d 27.2,
6
13
29.23, 32.7, 50.4, 52.7, 55.3, 108.5, 127.2, 128.1, 128.9, 144.1,
+
2
,3,7,9-tetraazaspiro[4.5]dec-3-en-1-one (4f). White crystalline
149.3, 175.1, 194.2; MS (m/z): 271 (M + H) . Anal. Calcd for
ꢀ
solid; (yield 90%); mp 232–234 C; IR (KBr): n = 3364, 3202,
C16H18N2O2: C, 71.09; H, 6.71, N, 10.36. Found: C, 71.16, H,
6.69; N 10.33.
À1
1
3
6
078, 1722, 1684, 1616 cm ; H NMR (DMSO-d , 300 MHz,
mixture-major isomer only): d 2.33 (s, 3H, CH ), 3.63 (s, 6H,
4-(4-Methoxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-
pyrazole-3-one (8b). Brown red solid; (yield 58%); mp
3
OCH ), 5.06 (s, 2H, CH), 6.82–7.28 (m, 13H, ArH), 7.24
3
1
3
ꢀ
(
s, 2H, NH); C NMR (DMSO-d
6
, 75 MHz): d 18.6, 55.2,
124–126 C; IR (KBr): n = 3060, 1692, 1620, 1586, 1090,
À1
1
5
1
4
5
6.1, 62.5, 114.2, 115.8, 119.1, 120.6, 121.7, 126.2, 127.6,
760 cm ; H NMR (CDCl
3.78 (s, 3H, OCH ), 6.99 (d, J = 12.2 Hz, 2H), 7.18
(t, J = 12.4 Hz, 1H), 7.34 (s, 1H), 7.41 (t, J = 8.4 Hz, 2H), 7.95
3 3
, 300 MHz): d 2.35 (s, 3H, CH ),
28.1, 128.4, 129.7, 138.3, 152.2, 168.8, 176.6; MS (m/z):
3
+
87 (M + H) . Anal. Calcd for C H N O S: C, 66.65; H,
2
7 26 4 3
1
3
.39; N, 11.51. Found: C, 66.78; H, 5.54; N, 11.38.
,10-Bis-(4-chlorophenyl)-4-methyl-2-phenyl-8-thioxo-2,3,7,9-
(d, J = 9.6 Hz, 2H), 8.58 (d, J = 8.4 Hz, 2H); C NMR (CDCl3,
6
75 MHz): d 18.3, 57.1, 114.9, 115.7, 120.3, 124.8, 125.6,
tetraazaspiro[4.5]dec-3-en-1-one (4g). White crystalline solid;
127.1, 128.3, 128.9, 130.2, 132.3, 143.7, 152.9, 168.4; MS (m/z):
ꢀ
+
(
yield 91%); mp 292–294 C; IR (KBr): n = 3382, 3220, 3090,
16 2 2
293 (M + H) . Anal. Calcd for C18H N O : C, 73.95; H, 5.52, N,
À1
1
1
720, 1692, 1608 cm
;
H NMR (DMSO-d , 300 MHz,
9.58. Found: C, 74.16, H, 5.70; N 9.38.
6
mixture-major isomer only): d 2.32 (s, 3H, CH ), 5.07 (s, 2H,
3
1
3
CH), 6.82–7.58 (m, 13H, ArH), 7.31 (s, 2H, NH); C NMR
DMSO-d , 75 MHz): d 18.8, 57.3, 62.6, 114.7, 116.4, 119.8,
20.1, 122.4, 125.7, 127.6, 128.3, 128.9, 129.3, 137.8, 168.9,
(
1
1
6
Acknowledgments. Financial assistance from the University
Grants Commission (34-349/08/SR) and the Council for
Scientific and Industrial Research (01/2248/08/EMR-II) New
Delhi is gratefully acknowledged. We are thankful to the
Central Drug Research Institute (CDRI), Lucknow, for the
elemental and spectral analyses. We are also thankful to
Chemind Diagnosis and Biosolutions Laboratory, Jaipur, for
the antimicrobial screening of the samples.
+
76.4; MS (m/z): 496 (M + H) . Anal. Calcd for C H
2
5 20
Cl N OS: C, 60.61; H, 4.07; N, 11.31. Found: C, 60.75; H,
2
4
4
.23; N, 11.45.
,10-Bis-(4-bromophenyl)-4-methyl-2-phenyl-8-thioxo-2,3,7,9-
6
tetraazaspiro[4.5]dec-3-en-1-one (4h). White crystalline solid;
ꢀ
(
1
yield 91%); mp 226–228 C; IR (KBr): n = 3376, 3214, 3088,
À1
1
718, 1698, 1614 cm
;
H NMR (DMSO-d
6
, 300 MHz,
mixture-major isomer only): d 2.31 (s, 3H, CH
CH), 6.91–7.68 (m, 13H, ArH), 7.32 (s, 2H, NH); C NMR
DMSO-d , 75 MHz): d 18.7, 57.5, 62.7, 113.9, 116.7, 119.4,
3
), 5.07 (s, 2H,
1
3
REFERENCES AND NOTES
(
6
1
1
20.6, 122.3, 125.7, 127.2, 128.6, 129.4, 130.1, 138.7, 168.3,
[1] Constable, D. J. C.; Gonzalez, C. J.; Henderson, R. K. Org
Process Res Dev 2007, 11, 133.
+
76.9; MS (m/z): 585 (M + H) . Anal. Calcd for C25
OS: C, 51.39; H, 3.45; N, 9.59. Found: C, 51.57; H,
.28; N, 9.72.
-Methyl-6,10-bis-(4-nitrophenyl)-2-phenyl-8-thioxo-2,3,7,9-
H
20
[2] Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and
2 4
Br N
3
Practice; Oxford University Press: Oxford, UK, 1998.
[
[
[
3] Tanaka, K.; Toda, F. Chem Rev 2000, 100, 1025.
4] Clark, J. H.; Tavener, S. J. Org Process Res Dev 2007, 11,149.
5] Martins, M. A. P.; Frizzo, C. P.; Moreira, D. N.; Zanatta, N.;
4
tetraazaspiro[4.5]dec-3-en-1-one (4i). White crystalline solid;
ꢀ
(
yield 84%); mp 254–256 C; IR (KBr): n = 3380, 3220, 3094,
Bonacorso, H. G.; Chem Rev 2008, 108,2015.
[6] Candeias, N. R.; Branco, L. C.; Gois, P. M. P.; Afonso, C. A. M.;
Trindade, A. F. Chem Rev 2009, 109, 2703.
À1
1
1
720, 1696, 1622 cm
;
H NMR (DMSO-d
6
, 300 MHz,
mixture-major isomer only): d 2.33 (s, 3H, CH
3
), 5.21 (s, 2H,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet