Pang et al.
FULL PAPER
for C41H29N4O3Br2 [M+H]+ 783.0606, found 783.0608.
found 783.0610.
3,3-Di-4-chlorobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8b)
3,3-Di-3-chlorobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8g) Brown solid; 89%
Gray solid; 93%
1
1
yield; m.p. 183—185 ℃; H NMR (DMSO-d6, 300
MHz) δ: 8.40 (s, 2H), 8.11—7.33 (m, 25H), 6.64 (d, J=
10.0 Hz, 1H); 13C NMR (DMSO-d6, 75 MHz) δ: 162.07,
149.74, 147.57, 146.15, 136.61, 133.59, 132.01, 130.04,
129.52, 129.21, 129.05, 128.52, 128.39, 127.55, 127.09,
126.99, 126.72, 123.97, 121.56, 119.93, 118.06, 113.94,
81.50; IR (KBr) ν: 3203, 3054, 3021, 1656, 1586, 1553,
yield; m.p. 177—179 ℃; H NMR (DMSO-d6, 300
MHz) δ: 8.47 (s, 2H), 8.12—7.37 (m, 25H), 6.65 (d, J=
9.9 Hz, 1H); 13C NMR (DMSO-d6, 75 MHz) δ: 161.69,
149.73, 147.80, 146.20, 135.33, 135.29, 133.54, 133.28,
130.41, 130.04, 129.21, 129.04, 128.38, 127.53, 127.32,
127.13, 126.99, 126.72, 126.39, 123.97, 121.55, 119.94,
118.05, 113.93, 81.49; IR (KBr) ν: 3216, 3062, 3017,
-1
-1
1511, 1486, 1358, 1270, 1005 cm ; HRMS (ESI) calcd
1652, 1602, 1565, 1507, 1474, 1358, 1258, 1001 cm ;
for C41H29N4O3Cl2 [M+H]+ 695.1617, found 695.1603.
3,3-Di-4-nitrobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8c) Yellow solid; 96%
HRMS (ESI) calcd for C41H29N4O3Cl2 [M + H] +
695.1617, found 695.1616.
3,3-Di-3-nitrobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8h) Light yellow solid;
85% yield; m.p. 189—193 ℃; 1H NMR (DMSO-d6, 300
MHz) δ: 8.75 (s, 2H), 8.47—7.36 (m, 25H), 6.67 (d, J=
9.9 Hz, 1H); 13C NMR (DMSO-d6, 75 MHz) δ: 160.95,
149.72, 148.27, 147.73, 146.31, 134.70, 134.05, 133.43,
130.20, 130.04, 129.19, 129.04, 128.38, 127.52, 127.21,
126.99, 126.73, 126.25, 123.97, 122.26, 121.55, 119.96,
118.04, 113.93, 81.48; IR (KBr) ν: 3216, 3079, 3058,
1
yield; m.p. 189—192 ℃; H NMR (DMSO-d6, 300
MHz) δ: 8.42 (s, 2H), 8.35—7.34 (m, 25H), 6.65 (d, J=
10.4 Hz, 1H); 13C NMR (DMSO-d6, 75 MHz) δ: 161.50,
149.72, 149.24, 148.38, 146.35, 138.99, 133.42, 130.69,
130.05, 129.12, 128.38, 127.50, 127.23, 126.99, 126.74,
123.98, 123.55, 122.80, 121.55, 119.97, 118.04, 113.94,
81.48; IR (KBr) ν: 3207, 3050, 3025, 1664, 1598, 1561,
-1
1515, 1457, 1341, 1279,+1009 cm ; HRMS (ESI) calcd
-1
for C41H29N6O7 [M+H] 717.2098, found 717.2099.
3,3-Di-4-methoxybenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8d) Brown solid; 71%
1656, 1611, 1561, 1523, 1457, 1345, 1275,+1009 cm ;
HRMS (ESI) calcd for C41H29N6O7 [M+H] 717.2098,
found 717.2086.
1
yield; m.p. 179—181 ℃; H NMR (DMSO-d6, 300
3,3-Di-3-methylbenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8i) Gray solid; 62% yield;
MHz) δ: 8.42 (s, 2H), 8.14—7.04 (m, 25H), 6.66 (d, J=
9.9 Hz, 1H), 3.83 (s, 6H); 13C NMR (DMSO-d6, 75
MHz) δ: 162.56, 161.99, 149.76, 146.62, 145.93, 133.83,
130.02, 129.55, 129.22, 129.04, 128.38, 127.60, 126.93,
126.70, 125.43, 125.39, 123.96, 121.55, 119.88, 118.07,
113.93, 113.66, 81.51, 55.36; IR (KBr) ν: 3224, 3050,
3029, 16-44, 1598, 1548, 1503, 1461, 1358, 1250, 1167,
1
m.p. 174—176 ℃; H NMR (DMSO-d6, 300 MHz) δ:
8.43 (s, 2H), 8.15—7.36 (m, 25H), 6.67 (d, J=9.9 Hz,
1H), 2.38 (s, 6H); 13C NMR (DMSO-d6, 75 MHz) δ:
163.22, 149.74, 147.09, 146.04, 137.75, 133.72, 133.32,
132.28, 130.03, 129.21,129.04, 128.38, 128.30, 128.06,
127.60, 127.00, 126.86, 126.72, 124.73, 123.97, 121.56,
119.90, 118.06, 113.92, 81.51, 20.89; IR (KBr) ν: 3216,
3058, 30-17, 1664, 1598, 1586, 1528, 1457, 1353, 1279,
+
1
1005 cm ; HRMS (ESI) calcd for C43H35N4O5 [M+H]
687.2607, found 687.2604.
+
1
3,3-Di-4-methylbenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8e) Brown solid; 78%
1001 cm ; HRMS (ESI) calcd for C43H35N4O3 [M+H]
655.2709, found 655.2703.
1
yield; m.p. 194—196 ℃; H NMR (DMSO-d6, 300
3,3-Di-2-chlorobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8j) Yellow solid; 81%
MHz) δ: 8.44 (s, 2H), 8.13—7.31 (m, 25H), 6.65 (d, J=
9.9 Hz, 1H), 2.37 (s, 6H); 13C NMR (DMSO-d6, 75
MHz) δ: 162.97, 162.87, 161.83, 149.75, 146.94, 146.00,
141.77, 133.77, 130.47, 130.03, 129.22, 129.04, 128.93,
128.39, 127.61, 126.98, 126.71, 123.97, 121.56, 119.89,
118.06, 113.93, 81.51, 20.97; IR (KBr) ν: 3211, 3062,
3021, 1644, 1606, 1548, 1490, 1457, 1353, 1279, 100+9
1
yield; m.p. 175—177 ℃; H NMR (DMSO-d6, 300
MHz) δ: 8.40 (s, 2H), 8.11—7.33 (m, 25H), 6.64 (d, J=
10.0 Hz, 1H); 13C NMR (DMSO-d6, 75 MHz) δ: 162.48,
149.70, 147.39, 146.25, 145.79, 143.27, 135.89, 135.19,
133.37, 131.37, 130.40, 129.70, 129.28, 128.88, 128.70,
128.38, 127.16, 126.73, 126.49, 123.97, 121.55, 119.89,
118.05, 113.91, 81.36; IR (KBr) ν: 3203, 3050, 3025,
-1
cm ; HRMS (ESI) calcd for C43H35N4O3 [M+H]
-1
655.2709, found 655.2709.
1660, 1598, 1590, 1511, 1428, 1358, 1233, 1001 cm ;
3,3-Di-3-bromobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8f) Gray solid; 93% yield;
HRMS (ESI) calcd for C41H29N4O3Cl2 [M + H] +
695.1617, found 695.1607.
1
m.p. 173—176 ℃; H NMR (DMSO-d6, 300 MHz) δ:
3,3-Di-2-nitrobenzoic acid methylenehydrazino-
[3H]-naphtho[2,1-b]pyran (8k) Yellow solid; 88%
8.44 (s, 2H), 8.11—7.34 (m, 25H), 6.62 (d, J=9.9 Hz,
1H); 13C NMR (DMSO-d6, 75 MHz) δ: 161.63, 149.73,
147.84, 146.20, 135.48, 134.44, 133.51, 130.67, 130.15,
130.04, 129.19, 129.04, 128.38, 127.52, 127.14, 126.99,
126.77, 126.71, 123.98, 121.73, 121.54, 119.94, 118.05,
113.93, 81.47; IR (KBr) ν: 3216, 3054, 3016, 1660,
1
yield; m.p. 192—196 ℃; H NMR (DMSO-d6, 300
MHz) δ: 8.40 (s, 2H), 8.11—7.33 (m, 25H), 6.64 (d, J=
10.0 Hz, 1H); 13C NMR (DMSO-d6, 75 MHz) δ: 167.83,
161.86, 149.70, 147.70, 146.89, 145.95, 143.77, 134.22,
133.97, 132.96, 131.17, 130.62, 129.99, 129.53, 128.36,
127.20, 126.56, 124.31, 123.95, 123.37, 121.50, 119.91,
118.01, 113.90, 81.35; IR (KBr) ν: 3199, 3058, 3025,
-1
1602, 1561, 1506, 1465, 1353, 1262, 1001 cm ; HRMS
(ESI) calcd for C41H29N4O3Br2 [M+H]+ 783.0606,
1682
© 2011 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2011, 29, 1677— 1684