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Magnetically Retrievable Nano Crystalline Nickel Ferrite-Catalyzed
HR-MS (ESI-TOF): m/z=256.0779 [M+H]+, calculated for
C15H10FNO2: 256.0774.
125.1, 126.0, 127.6, 129.7, 141.0, 150.0, 150.5, 151.0, 151.7,
162.0; anal. calcd. for C18H11ClN2O2: C 66.99, H 3.44, N
8.68%; found: C 66.95, H 3.47, N 8.66%; HR-MS (ESI-
4-[(2-Chlorophenyl)amino]-2H-chromen-2-one
Yield: 95% (0.257 g); characteristics: white crystalline solid;
mp 2448C; IR (KBr): n=3262, 1667, 1609, 1480 cmÀ1
(2d):
TOF):
m/z=323.0580
[M+H]+,
calculated
for
;
C18H11ClN2O2: 323.0587.
1H NMR (300 MHz, DMSO-d6): d=4.64 (1H, s), 7.36–7.50
(5H, m), 7.65 (2H, t, J=7.5 Hz), 8.23 (1H, d, J=7.8 Hz),
9.41 (1H, s); 13C NMR (75 MHz, DMSO-d6): d=85.3, 114.5,
117.5, 123.2, 124.2, 129.1, 129.8, 130.5, 130.9, 131.8, 132.9,
135.4, 153.3, 153.8, 161.7; anal. calcd. for C15H10ClNO2: C
66.31, H 3.71, N 5.16%; found: C 66.35, H 3.72, N 5.12%;
HR-MS (ESI-TOF): m/z=272.0480 [M+H]+, calculated for
C15H10ClNO2: 272.0478.
4-(meta-Tolylamino)-2H-chromen-2-one (2j): Yield: 92%
(0.230 g); characteristics: white crystalline solid; mp 2128C;
IR (KBr): n=3261, 1662, 1607, 1547 cmÀ1
;
1H NMR
(300 MHz, DMSO-d6): d=2.25 (3H, s), 5.20 (1H, s), 6.99–
7.31 (6H, m), 7.54 (1H, t, J=7.8 Hz), 8.14 (1H, d, J=
8.1 Hz), 9.17 (1H, s); 13C NMR (75 MHz, DMSO-d6): d=
21.3, 84.7, 114.9, 117.4, 122.5, 123.2, 124.0, 125.9, 127.1,
129.7, 132.7, 138.5, 139.5, 152.9, 153.8, 161.9; anal. calcd. for
C16H13NO2: C 76.48, H 5.21, N 5.57%; found: C 76.44, H
5.23, N 5.59%; HR-MS (ESI-TOF): m/z=252.1020 [M+
H]+, calculated for C16H13NO2: 252.1025.
3-(4-Chlorophenylamino)-chromen-2-one (2e): Yield:
97% (0.262 g); characteristics: light yellow crystalline solid;
mp 2388C; IR (KBr): n=3398, 1679, 1577 cmÀ1 1H NMR
;
(300 MHz, CDCl3): d=6.70 (1H, s), 7.01–7.29 (9H, m);
13C NMR (75 MHz, CDCl3): d=108.6, 115.8, 120.3, 121.4,
121.5, 124.5, 125.3, 126.8, 128.1, 128.6, 129.2, 129.3, 129.4,
138.0, 148.1, 159.3; anal. calcd. for C15H10ClNO2: C 66.31, H
3.71, N 5.16%; found: C 66.33, H 3.73, N 5.12%; HR-MS
(ESI-TOF): m/z=272.0473 [M+H]+, calculated for
C15H10ClNO2: 272.0478.
3-(4-Methoxyphenylamino)-chromen-2-one (2k): Yield:
95% (0.253 g); characteristics: light yellow crystalline solid;
mp 2118C; IR (KBr): n=3401, 1705, 1566 cmÀ1 1H NMR
;
(300 MHz, CDCl3): d=3.76 (3H, s), 6.50 (1H, s), 6.80 (1H,
s), 6.87 (2H, d, J=8.7 Hz), 7.08–7.20 (6H, m); 13C NMR
(75 MHz, CDCl3): d=55.5, 106.9, 114.8, 114.9, 116.0, 121.2,
123.8, 123.9, 124.7, 125.3, 126.3, 130.8, 132.4, 148.2, 156.5,
159.8; anal. calcd. for C16H13NO3: C 71.90, H 4.90, N
5.24%.; found: C 71.92, H 4.93, N 5.20%; HR-MS (ESI-
TOF): m/z=268.0979 [M+H]+, calculated for C16H13NO3:
268.0974.
3-{[5-(Dimethylamino)pyrimidin-2-yl]amino}-2H-chro-
men-2-one (2f): Yield: 90% (0.253 g); characteristics: white
crystalline solid; mp 2668C; IR (KBr): n=3402, 1708,
1596 cmÀ1 1H NMR (300 MHz, CDCl3): d=3.05 (6H, s),
;
5.96 (1H, d, J=6.0 Hz), 7.14–7.37 (4H, m), 7.79 (1H, s),
7.93 (1H, d, J=6.0 Hz), 8.63 (1H, s); 13C NMR (75 MHz,
CDCl3): d=37.3, 96.2, 116.1, 118.0, 120.9, 124.7, 125.9, 126.8,
127.7, 148.9, 155.5, 158.7, 159.3, 162.5; anal. calcd. for
C15H14N4O2: C 63.82, H 5.00, N 19.85%; found: C 63.85, H
5.02, N 19.81%; HR-MS (ESI-TOF): m/z=283.1190 [M+
H]+, calculated for C15H14N4O2: 283.1195.
3-(meta-Tolylamino)chromen-2-one (2l): Yield: 94%
(0.235 g); characteristics: light yellow crystalline solid; mp
2238C; IR (KBr): n=3391, 1688, 1534 cmÀ1
;
1H NMR
(300 MHz, CDCl3): d=2.24 (3H, s), 6.62 (1H, s), 6.79 (1H,
d, J=7.5 Hz), 6.89–7.20 (8H, m); 13C NMR (75 MHz,
CDCl3): d=21.5, 108.4, 116.1, 117.6, 121.0, 121.4, 124.4,
124.8, 125.5, 126.7, 129.4, 139.6, 148.4, 159.8; anal. calcd. for
C16H13NO2: C 76.48, H 5.21, N 5.57%; found: C 76.45, H
5.23, N 5.59%; HR-MS (ESI-TOF): m/z=252.1029 [M+
H]+, calculated for C16H13NO2: 252.1025.
3-(Pyrimidin-2-ylamino)-chromen-2-one (2g): Yield: 93%
(0.222 g); characteristics: white crystalline solid; mp 2298C;
IR (KBr): n=3370, 1718, 1629 cmÀ1 1H NMR (300 MHz,
;
CDCl3): d=6.78 (1H, t, J=4.8 Hz), 7.18–7.31 (3H, m), 7.46
(1H, dd, J1 =6.9 Hz, J2 =1.2 Hz), 8.08 (1H, s), 8.46 (2H, d,
J=4.8 Hz), 8.70 (1H, s); 13C NMR (75 MHz, CDCl3): d=
113.8, 116.2, 118.9, 124.8, 127.1, 128.3, 141.0, 151.0, 157.9,
162.5, 167.9; anal. calcd. for C13H9N3O2: C 65.27, H 3.79, N
17.56%; found: C 65.24, H 3.77, N 17.59%; HR-MS (ESI-
TOF): m/z=240.0771 [M+H]+, calculated for C13H9N3O2:
240.0773.
3-(Phenylamino)-2H-chromen-2-one (2m): Yield: 92%
(0.218 g); characteristics: white crystalline solid; mp 2098C;
IR (KBr): n=3369, 1701, 1598 cmÀ1 1H NMR (300 MHz,
;
CDCl3): d=6.72 (1H, s), 7.01–7.34 (10H, m); 13C NMR
(75 MHz, CDCl3): d=108.4, 116.0, 120.5, 120.6, 120.8, 123.4,
124.7, 125.4, 126.7, 129.2, 129.4, 129.5, 139.6, 148.3, 159.7;
anal. calcd. for C15H11NO2: C 75.94, H 4.67, N 5.90%;
found: C 75.91, H 4.69, N 5.92%; HR-MS (ESI-TOF): m/z=
238.0866 [M+H]+, calculated for C15H11NO2: 238.0868.
2-Phenylaminophenol (2n): Yield: 96% (0.177 g); charac-
3-(Pyridin-2-ylamino)-chromen-2-one (2h): Yield: 97%
(0.230 g); characteristics: white crystalline solid; mp 2418C;
IR (KBr): n=3339, 1708, 1598 cmÀ1 1H NMR (300 MHz,
;
1
teristics: dark brown oil; H NMR (300 MHz, CDCl3): d=
CDCl3): d=6.71–6.8 (2H, m), 7.17–7.30 (3H, m), 7.43–7.53
(3H, m), 8.27 (1H, t, J=2.4 Hz), 8.79 (1H, s); 13C NMR
(75 MHz, CDCl3): d=112.2, 116.1, 116.2, 116.8, 121.1, 124.8,
126.1, 126.9, 127.6, 137.4, 147.6, 148.8, 154.4, 159.9; anal.
calcd. for C14H10N2O2: C 70.58, H 4.23, N 11.76%; found: C
5.26 (s, 1H), 5.76 (s, 1H), 6.76–6.79 (m, 3H), 6.85–6.91 (m,
2H), 6.99 (d, J=7.5 Hz, 1H), 7.12 (t, J=7.2 Hz, 1H), 7.17–
7.25 (m, 2H); 13C NMR (75 MHz, CDCl3): d=116.3, 116.7,
121.0, 121.9, 124.3, 126.4, 128.3, 128.6, 145.5, 151.5; anal.
calcd. for C12H11NO: C 77.81, H 5.99, N 7.56%; found: C
77.83, H 5.96, N 7.58%; HR-MS (ESI-TOF): m/z=186.0919
[M+H]+, calculated for C12H11NO: 186.0919.
70.56,
H 4.25, N 11.75%; HR-MS (ESI-TOF): m/z=
239.0829 [M+H]+, calculated for C14H10N2O2: 239.0821.
3-(4-Chloroquinolin-7-ylamino)-chromen-2-one
(2i):
1-tert-Butyl-4-phenoxybenzene (3a): Yield: 90% (0.203 g);
characteristics: colorless liquid; 1H NMR (300 MHz,
CDCl3): d=1.24 (9H, s), 6.80–7.27 (9H, m); 13C NMR
(75 MHz, CDCl3): d=31.6, 34.3, 118.4, 118.5, 118.6, 118.7,
122.9, 126.3, 126.4, 129.4, 129.5, 146.1, 154.7, 157.6; anal.
calcd. for C16H18O: C 84.91, H 8.02%; found: C 84.88, H
Yield: 91% (0.293 g); characteristics: yellow crystalline
solid; mp 2898C; IR (KBr): n=3423, 2399, 1764 cmÀ1
;
1H NMR (300 MHz, CDCl3 +DMSO-d6): d=7.04 (1H, s),
7.26–7.60 (5H, m), 7.73 (1H, s), 7.91 (1H, s), 8.11 (1H, s),
8.31 (1H, d, J=8.7 Hz), 8.61 (1H, s); 13C NMR (75 MHz,
CDCl3 +DMSO-d6): d=110.5, 116.1, 120.0, 124.8, 125.0,
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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