H. Kaur et al. / European Journal of Medicinal Chemistry 45 (2010) 2777e2783
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5.1.4.9. 2-[40-(4-NN0-dimethylaminobenzylidenylamino-5-(N9-car-
bazolylmethylene)]-1, 3, 4-thiadiazole (4i). Yield 81% (methanol); m.
p.134 ꢀC; IR (KBr, nmax in cmꢁ1): 3429 (eOH),1614 (C.C of aromatic
ring), 1588 (eC¼N), 1579 (N¼CH), 711 (CeSeC); 1H NMR
5.1.5.4. 9-[40-{4-NN0-Dimethylaminophenyl}-3-chloro-2-oxo-azeti-
din-100-yl-10, 30, 40-oxadiazol-50-yl] methylene carbazole (5d). Yield
85% (acetone); m.p. 126 ꢀC; IR (KBr, nmax in cmꢁ1): 1748 (C¼O), 1615
(C.C of aromatic ring), 1585 (eC¼N), 1022 (CeOeC), 1011 (CeCl);
(CDCl3þDMSOd6)
d
in ppm: 1.75 (s, 6H, N(CH3)2), 3.84 (s, 2H,
1H NMR (CDCl3 þ DMSOd6)
d in ppm: 1.82 (s, 6H, N(CH3)2), 3.77 (s,
2H, eNeCH2), 5.03 (d, 1H, J ¼ 5.10 Hz, CHCl), 5.54 (d, 1H, J ¼ 5.0 Hz,
eNeCH2), 8.17e7.18 (m, 12H, AreH), 8.67 (s, 1H, eN¼CH); 13C NMR
(CDCl3)
d
ppm: 160.0, 153.4, 135.5, 128.3, 125.9, 122.9, 121.7, 121.4,
eNeCHAr), 8.12e7.18 (m, 12H, AreH); 13C NMR (CDCl3)
d ppm:
119.8, 111.9, 109.6, 58.1, 40.2. Anal. Calcd. for C23H21N4S: C, 70.04; H,
5.14; N, 17.01; Found: C, 70.05; H, 5.18; N, 17.03%.
162.2, 149.1, 135.5, 133.0, 129.2, 122.9, 121.7, 121.4, 119.8, 112.7, 109.6,
62.8, 58.1, 40.2. Anal. Calcd. for C26H22N5O2Cl: C, 66.17; H, 4.69; N,
14.83; Found: C, 66.19, H, 4.66; N, 14.80%.
5.1.4.10. 2-[40-(2-bromobenzylidenylamino-5-(N9-carbazolylmethylene)]-
1, 3, 4-thiadiazole (4j). Yield 85% (acetone); m.p. 135 ꢀC; IR (KBr, nmax in
cmꢁ1): 1617 (C.C of aromatic ring), 1591 (eC¼N), 1576 (N¼CH), 710
5.1.5.5. 9-[40-{2-Bromophenyl}-3-chloro-2-oxo-azetidin-100-yl-10, 30,
40-oxadiazol-50-yl] methylene carbazole (5e). Yield 85% (petroleum
ether); m.p.132 ꢀC; IR (KBr, nmax in cmꢁ1): 1749 (C¼O),1612 (C.C of
aromatic ring), 1584 (eC¼N), 1020 (CeOeC), 1006 (CeCl), 609
(CeSeC), 612 (CeBr); 1H NMR (CDCl3þDMSOd6)
d in ppm: 3.91 (s, 2H,
eNeCH2), 8.16e7.17 (m, 12H, AreH), 8.63 (s, 1H, eN¼CH); 13C NMR
(CeBr); 1H NMR (CDCl3 þ DMSOd6)
d in ppm: 3.76 (s, 2H, eNeCH2),
(CDCl3) d ppm: 160.0, 135.5, 135.3, 132.8, 130.1, 127.8, 122.9, 121.7, 121.6,
5.04 (d, 1H, J ¼ 5.10 Hz, CHCl), 5.56 (d, 1H, J ¼ 5.10 Hz, eNeCHAr),
121.4, 119.8, 109.6, 127.1, 58.1. Anal. Calcd. for C22H15N4SBr: C: 59.06, H:
3.38, N: 12.52; Found: C, 59.16; H, 3.29; N, 12.45%.
8.09e7.17 (m, 12H, AreH); 13C NMR (CDCl3)
d ppm: 162.2, 145.7,
135.5, 132.5, 128.9, 127.5, 129.1, 122.9, 121.9, 121.7, 121.4, 119.8, 109.6,
61.3, 59.0, 58.1. Anal. Calcd. for C24H16N4O2ClBr: C, 58.77; H, 3.17; N,
11.03; Found: C, 58.70; H, 3.19; N, 11.24%.
5.1.5. Preparation of 9-[40-{Substitutedphenyl}-3-chloro-2-oxo-azetidin-
100-yl-10, 30, 40-oxa/thiadiazol-50-yl] methylene carbazoles 5a-j
To a stirred solution of 2-[40-(Substitutedbenzylidenylamino-5-
(N9-carbazolylmethylene)]-1, 3, 4-oxa/thiadiazoles (4a-j, 0.05 mol)
in dioxan (100 mL), chloro acetyl chloride (0.05 mol) was added
dropwise at 0e5 ꢀC temperature in presence of triethyl amine. The
reaction mixture was stirred for about 6 h and the precipitated
amine hydrochloride was filtered off. The filtrate was refluxed for
12 h and the separated solid was recrystallized from appropriate
solvents to furnish compounds 5a-j.
5.1.5.6. 9-[40-{4-Hydroxyphenyl}-3-chloro-2-oxo-azetidin-100-yl-10, 30,
40-thiadiazol-50-yl] methylene carbazole (5f). Yield 85% (acetone); m.
p.129 ꢀC. IR (KBr, nmax in cmꢁ1): 3439 (OH),1751 (C¼O),1618 (C.C of
aromatic ring), 1589 (eC¼N), 1008 (CeCl), 712 (CeSeC); 1H NMR
(CDCl3þDMSOd6)
d in ppm: 3.84 (s, 2H, eNeCH2), 5.02 (d, 1H,
J ¼ 5.12 Hz, CHCl), 5.55 (d, 1H, J ¼ 5.0 Hz, eNeCHAr), 8.03e7.19 (m,
12H, AreH), 11.17 (s, 1H, OH); 13C NMR (CDCl3)
d
ppm: 163.4, 162.2,
156.5, 136.1, 135.5, 127.0, 122.9, 121.7, 121.4, 119.8, 115.7, 109.6, 62.8,
62.0, 58.1. Anal. Calcd. for C24H17N4O2SCl: C, 62.53; H, 3.71; N, 12.15;
Found: C, 62.59; H, 3.79; N, 12.26%.
5.1.5.1. 9-[40-{4-Hydroxyphenyl}-3-chloro-2-oxo-azetidin-100-yl-10, 30,
40-oxadiazol-50-yl] methylene carbazole (5a). Yield 76% (ethanol); m.
p.124 ꢀC; IR (KBr, nmax in cmꢁ1): (eOH) 3429, 1752 (C¼O), 1619 (C.
C
5.1.5.7. 9-[40-{2,4-Dihydroxyphenyl}-3-chloro-2-oxo-azetidin-100-yl-10,
30, 40-thiadiazol-50-yl] methylene carbazole (5g). Yield 85% (meth-
anol); m.p. 128 ꢀC. IR (KBr, nmax in cmꢁ1): 3438 (OH), 1752 (C¼O),
1614 (C.C of aromatic ring),1583(eC¼N),1012 (CeCl), 711 (CeSeC);
of aromatic ring),1585 (eC¼N),1012 (CeOeC),1004 (CeCl); 1H NMR
(CDCl3þDMSOd6)
d in ppm: 3.92 (s, 2H, eNeCH2), 5.00 (d, 1H,
J ¼ 5.12 Hz, CHCl), 5.60 (d, 1H, J ¼ 5.0 Hz, eNeCHAr), 7.36e8.36 (m,
12H, AreH), 11.18 (s, 1H, OH). 13C NMR (CDCl3)
d
ppm: 162.2, 156.5,
1H NMR (CDCl3þDMSOd6)
d in ppm: 3.78 (s, 2H, eNeCH2), 5.05 (d,
136.1, 135.5, 127.0, 122.9, 121.7, 121.4, 119.8, 115.7, 109.6, 68.8, 68.0,
58.1. Anal. Calcd. for C24H17N4O3Cl: C, 64.79; H, 3.85; N,12.59; Found:
C, 64.99; H, 3.52; N, 12.49%.
1H, J ¼ 5.0 Hz, CHCl), 5.54 (d,1H, J ¼ 5.0 Hz, eNeCHAr), 8.04e7.16 (m,
11H, AreH), 11.21 (s, 2H, 2 ꢂ OH); 13C NMR (CDCl3)
d ppm: 163.4,
162.2, 157.9, 155.4, 135.5, 129.7, 123.5, 122.9, 121.7, 121.4, 119.8, 109.6,
108.3, 103.4, 62.3, 58.1, 56.6. Anal. Calcd. for C24H17N4O3SCl: C, 60.44;
H, 3.59; N, 17.74; Found: C, 60.38; H, 3.42; N, 11.61%.
5.1.5.2. 9-[40-{2,4-Dihydroxyphenyl}-3-chloro-2-oxo-azetidin-100-yl-10,
30, 40-oxadiazol-50-yl] methylene carbazole (5b). Yield 85% (ethanol);
m.p. 126 ꢀC. IR (KBr, nmax in cmꢁ1): 3429 (eOH), 1751 (C¼O), 1613
(C.C of aromatic ring), 1592 (eC¼N), (CeOeC) 1020, 1003 (CeCl);
5.1.5.8. 9-[40-{4-hydroxy-3-methoxyphenyl}-3-chloro-2-oxo-azeti-
din-100-yl-10, 30, 40-thiadiazol -50-yl] methylene carbazole (5h). Yield
85% (ethanol); m.p. 131 ꢀC. IR (KBr, nmax in cmꢁ1): 3543 (OH),: 1750
(C¼O),1619 (C.C of aromatic ring),1585 (eC¼N),1221 (OCH3),1014
1H NMR (CDCl3 þ DMSOd6)
d in ppm: 3.89 (s, 2H, eNeCH2), 5.05 (d,
1H, J ¼ 5.0 Hz, CHCl), 5.59 (d, 1H, J ¼ 5.0 Hz, eNeCHAr), 8.15e7.17 (m,
11H, AreH), 11.20 (s, 2H, 2 ꢂ OH). 13C NMR (CDCl3)
d ppm: 162.2,
(CeCl), 710 (CeSeC); 1H NMR (CDCl3 þ DMSOd6)
d in ppm: 3.39 (s,
3H, OCH3), 3.79 (s, 2H, eNeCH2), 5.04 (d, 1H, J ¼ 5.10 Hz, CHCl), 5.61
157.9, 155.4, 135.5, 129.7, 123.5, 122.9, 121.7, 121.4, 119.8, 109.6, 108.3,
62.3, 58.1,103.4, 56.6. Anal. Calcd. for C24H17N4O4Cl: C, 62.54; H, 3.71;
N, 12.15; Found: C, 62.51; H, 3.62; N, 12.18%.
(d, 1H, J ¼ 5.0 Hz, eNeCHAr), 8.07e7.18 (m, 11H, AreH), 11.23 (s, 1H,
OH); 13C NMR (CDCl3)
d ppm: 163.4, 162.2, 146.7, 147.3, 137.1, 135.5,
122.9, 121.7, 121.4, 119.8, 115.4, 110.2, 109.6, 62.0, 63.1, 58.1, 56.1.
Anal. Calcd. for C25H19N4O3SCl: C, 61.16; H, 3.90; N, 11.41; Found: C,
61.18; H, 3.85; N, 11.55%.
5.1.5.3. 9-[40-{4-hydroxy-3-methoxyphenyl}-3-chloro-2-oxo-azeti-
din-100-yl-10, 30, 40-oxadiazol-50-yl] methylene carbazole (5c). Yield
85% (DMF); m.p. 128 ꢀC; IR (KBr, nmax in cmꢁ1): 3429 (eOH), 1749
(C¼O), 1615 (C.C of aromatic ring), 1581 (eC¼N), 1220 (OCH3),
5.1.5.9. 9-[40-{4-NN0-Dimethylaminophenyl}-3-chloro-2-oxo-azeti-
din-100-yl-10, 30, 40-thiadiazol-50-yl] methylene carbazole (5i). Yield
85% (methanol); m.p. 130 ꢀC. IR (KBr, nmax in cmꢁ1): 1743C¼O),1614
(C.C of aromatic ring), 1588 (eC¼N), 1013 (CeCl), 709 (CeSeC); 1H
1025 (CeOeC), 1009 (CeCl); 1H NMR (CDCl3)
d in ppm: 3.37 (s, 3H,
OCH3), 3.81 (s, 2H, eNeCH2), 5.01 (d, 1H, J ¼ 5.12 Hz, CHCl), 5.62 (d,
1H, J ¼ 5.10 Hz, eNeCHAr), 8.02e7.18 (m, 11H, AreH), 11.19 (s, 1H,
OH); 13C NMR (CDCl3)
d
ppm: 162.2, 146.7, 147.3, 137.1, 135.5, 122.9,
NMR (CDCl3þDMSOd6)
d in ppm: 1.77 (s, 6H, N(CH3)2), 3.80 (s, 2H,
121.7, 121.4, 119.8, 119.3, 115.4, 110.2, 109.6, 62.0, 63.1, 58.1, 56.1.
Anal. Calcd. for C25H19N4O4Cl: C, 63.22; H, 4.03; N, 11.79; Found: C,
63.55; H, 3.68; N, 11.72%.
eNeCH2), 4.98 (d, 1H, J ¼ 5.0 Hz, CHCl), 5.66 (d, 1H, J ¼ 5.10 Hz,
eNeCHAr), 8.09e7.19 (m, 12H, AreH); 13C NMR (CDCl3)
ppm:
163.4, 162.2, 149.1, 135.5, 133.0, 129.2, 122.9, 121.7, 121.4, 119.8, 112.7,
d