2876
D.K. Barange et al. / Tetrahedron 67 (2011) 2870e2877
356.0723 and calcd for C17H12N2O5Na [MþNa]þ 379.0542, found
J¼7.4 Hz, 1H), 7.17 (d, J¼8.6 Hz, 2H), 6.83 (d, J¼8.6 Hz, 2H), 5.34 (s,
1H), 3.71 (s, 3H), 3.55 (s, 3H). 13C NMR (100 MHz, DMSO-d6)
165.1,
379.0524.
d
158.2, 157.7,140.4, 136.1,133.0,132.0,128.7,127.9,122.4, 122.2, 115.5,
111.8, 110.1, 45.7, 28.7, 20.5. MS (EI): (m/z) (relative intensity) 320
(Mþ, 100), 303 (45), 287 (22), 274 (18). HRMS (EI): calcd for
C19H16N2O3 (M)þ 320.1161, found 320.1164.
4.4.12. 4-Hydroxy-3-(2-nitro-1-(thiophen-2-yl)ethyl)-2H-chromen-
2-one (12l). Gray solid; mp: 173e174 ꢀC. FT-IR (KBr) /cmꢃ1 3443,
n
1705,1645,1518,1380,1240. 1H NMR (400 MHz, DMSO-d6)
d 8.07 (d,
J¼7.9 Hz, 1H), 7.65 (t, J¼6.8 Hz, 1H), 7.39e7.38 (m, 3H), 7.08 (s, 1H),
6.95 (s, 1H), 5.53 (t, J¼7.5 Hz, 1H), 5.40 (d, J¼8.0 Hz, 2H). 13C NMR
4.4.18. (E)-2-(Hydroxyimino)-3-(4-methoxyphenyl)-5-methyl-2,3-
(100 MHz, DMSO-d6)
d
162.1, 161.5, 152.2, 141.1, 132.6, 126.7, 125.5,
dihydrofuro[3,2-c]quinolin-4(5H)-one (15c). White solid; mp:
125.0, 124.1, 123.7, 116.4, 115.7, 103.5, 77.2, 34.5. MS (ESI): (m/z)
(relative intensity) 318 [(MþH)þ(60)], 271 (20), 257 (98), 216 (15).
HRMS (ESI): calcd for C15H11NO5S [MþH]þ 317.0358, found 317.0438
and calcd for C15H11NO6Na [MþNa]þ 340.0256, found 340.0259.
130e132 ꢀC. FT-IR (KBr) /cmꢃ1 3442, 1690, 1553, 1325, 1135. 1H
n
NMR (400 MHz, DMSO-d6)
d 10.27 (s, C]NeOH, (E) isomer, 1H),
7.87 (d, J¼7.7 Hz, 1H), 7.88 (t, J¼7.8 Hz, 1H), 7.62 (d, J¼8.6 Hz, 1H),
7.39 (t, J¼7.5 Hz, 1H), 7.15e7.06 (m, 4H), 5.34 (s, 1H), 3.54 (s, 3H),
1.98 (s, 3H). 13C NMR (100 MHz, DMSO-d6)
d 165.2, 158.2, 158.1,
4.4.13. 3-(1-(Furan-2-yl)-2-nitroethyl)-4-hydroxy-2H-chromen-2-
157.8, 140.3, 132.0, 129.1, 127.9, 122.4, 122.2, 115.4, 113.6, 111.8, 110.1,
55.0, 45.3, 28.7, 30. MS (EI): (m/z) (relative intensity) 336 (Mþ, 100),
319 (45), 287 (38). HRMS (EI): calcd for C19H16N2O4 (M)þ 336.1110,
found 336.1107.
one (12m). Light green colour; mp: 174e176 ꢀC. FT-IR (KBr)
n
/cmꢃ1
1
3443, 1650, 1600, 1510, 1355, 1215. H NMR (400 MHz, DMSO-d6)
d
8.04 (d, J¼6.8 Hz,1H), 7.65 (s,1H), 7.54 (s,1H), 7.39 (d, J¼6.8 Hz, 2H),
6.39e6.37 (m,1H), 6.26e6.23 (m,1H), 5.37e5.35 (m, 2H), 5.31e5.28
(m, 1H). 13C NMR (100 MHz, DMSO-d6)
162.5, 161.4, 152.3, 151.4,
d
4.4.19. (E)-3-(3,4-Dimethoxyphenyl)-2-(hydroxyimino)-5-methyl-
141.9,132.6,124.1,123.7,116.4,115.8,110.6,106.3,101.3, 75.2, 33.3. MS
(ESI): (m/z) (relative intensity) 301 (Mþ, 100), 437 (38), 324
[(MþNa)þ(98)], 302 [(MþH)þ(58)], 277 (24), 255 (95), 241 (62).
HRMS (ESI): calcd for C15H11NO6 [MþH]þ 302.0665, found 302.0674
and calcd for C15H11NO6Na [MþNa]þ 324.0484, found 324.0479.
2,3-dihydrofuro[3,2-c]quinolin-4(5H)-one (15d). White solid; mp:
166e168 ꢀC. FT-IR (KBr) /cmꢃ1 3435, 1650, 1570, 1390, 1215. 1H
n
NMR (400 MHz, DMSO-d6)
d 10.31 (s, C]NeOH, (E) isomer, 1H),
7.87 (d, J¼7.8 Hz, 1H), 7.74 (t, J¼7.8 Hz, 1H), 7.63 (d, J¼8.6 Hz, 1H),
7.39 (t, J¼7.5 Hz, 1H), 6.95 (s, 1H), 6.83 (d, J¼8.3 Hz, 1H), 6.70 (d,
J¼8.2 Hz, 1H), 5.35 (s, 1H), 3.70 (s, 6H), 3.59 (s, 3H). 13C NMR
4.4.14. 4-Hydroxy-3-(1-(naphthalen-2-yl)-2-nitroethyl)-2H-chro-
(100 MHz, DMSO-d6) d 165.1, 158.1, 157.8, 148.3, 147.9, 140.3, 132.0,
men-2-one (12n). Pale yellow solid; mp: 164e165 ꢀC. FT-IR (KBr)
n
/
128.3, 122.2, 119.7, 115.5, 112.6, 111.8, 111.7, 110.1, 55.5, 45.6, 28.8. MS
(EI): (m/z) (relative intensity) 366 (Mþ, 8), 350 (100), 335 (25).
HRMS (EI): calcd for C20H18N2O5 (M)þ 366.1216, found 366.1227.
cmꢃ1 3435, 1645, 1520, 1312, 1250. 1H NMR (400 MHz, DMSO-d6)
8.01 (d, J¼8.2 Hz,1H), 7.96e7.84 (m 4H), 7.64 (t, J¼8.2 Hz,1H), 7.56
(d, J¼8.2 Hz, 1H), 7.49e7.44 (m, 2H), 7.39e7.38 (m, 2H), 5.61e5.53
(m, 2H) 5.50e5.45 (m, 1H). 13C NMR (100 MHz, DMSO-d6)
162.2,
d
d
4.4.20. 3-(2,6-Dichlorophenyl)-2-(hydroxyimino)-5-methyl-2,3-di-
161.8, 152.2, 136.4, 132.8, 132.5, 132.0, 128.0, 127.7, 127.3, 126.2,
126.0, 125.8,124.0,123.6, 116.3, 115.8,104.0, 76.4, 38.6. MS (ESI): (m/
z) (relative intensity) 384 [(MþNa)þ(45)], 362 [(MþH)þ(75)], 315
(42), 301 (100), 283 (48), 266 (27), 223 (58). HRMS (ESI): calcd for
C21H15NO5 [MþH]þ 362.1028, found 362.1016 and calcd for
C21H15NO5Na [MþNa]þ 384.0848, found 384.0848.
hydrofuro[3,2-c]quinolin-4(5H)-one (15e). White solid; FT-IR (KBr)
n
/cmꢃ1 3434,1674,1520,1332. 1H NMR (400 MHz, DMSO-d6)
d 10.59
(s, C]NeOH, (Z) isomer, 1H), 10.31 (s, C]NeOH, (E) isomer, 1H),
7.89e7.87 (m, (E) isomer and (Z) isomer, 2H), 7.78e7.74 (m, (E)
isomer and (Z) isomer, 2H), 7.64e7.62 (m, (E) isomer and (Z) isomer,
2H), 7.55e7.52 (m, (E) isomer, 1H), 7.41e7.36 (m, (E) isomer and (Z)
isomer, 2H), 7.31e7.30 (m, (E) isomer, 2H), 6.19 (s, (E) isomer, 1H),
6.14 (s, (E) isomer, 1H), 3.56 (s, (Z) isomer, 3H), 3.54 (s, (E) isomer,
4.4.15. Deuterated compound of (12b
120e122 ꢀC. FT-IR (KBr) /cmꢃ1 3429, 2920, 1671, 1209, 552. 1H
NMR (400 MHz, DMSO-d6)
7.75 (d, J¼7.8 Hz, 1H), 7.55 (t, J¼7.8 Hz,
1H), 7.33e7.30 (m, 4H), 7.17 (d, J¼7.6 Hz, 2H), 5.14 (dd, J¼13.1,
6.9 Hz, 2H), 2.32 (s, 3H). 13C NMR (100 MHz, DMSO-d6)
167.7, 161.7,
*
). Yellow solid; mp:
n
3H). 13C NMR (100 MHz, DMSO-d6)
d 162.2, 158.4, 156.4, 157.7, 137.6,
d
137.2, 132.1,130.0, 129.2, 129.1, 128.4, 128.2, 128.1,127.9, 127.8, 126.6,
124.4, 122.7, 119.0, 116.8, 115.8, 92.1, 85.0, 30.4, 30.1, 29.5, 29.2. MS
(EI) (m/z) (relative intensity) 376.0 (Mþ2, 65), 374 (Mþ, 100), 323
(22), 296 (40), 248 (70). HRMS (EI): calcd for C18H12N2O3Cl2 (M)þ
374.0219, found 374.0231.
d
152.1, 136.2, 135.8, 132.4, 129.0, 127.4, 124.0, 123.5, 116.3, 115.7,
104.3, 76.3 (t, J¼21.0 Hz), 38.1, 20.5. MS (ESI) (m/z) (relative in-
tensity) 265 (8), 325 (14), 326(Mþ, 20). HRMS (ESI): calcd for
C18H14DNO5 (MþH)þ 326.1013 found 326.1004 and for
C18H14DNNaO5 (MþNa)þ 349.0911 found 349.0916.
4.4.21. 2-(Hydroxyimino)-3-(2-methoxyphenyl)-5-methyl-2,3-dihy-
drofuro[3,2-c]quinolin-4(5H)-one (15f). White solid; FT-IR (KBr) v/
cmꢃ1 3443, 1678, 1544, 1335, 113. 1H NMR (400 MHz, DMSO-d6)
4.4.16. (E)-2-(Hydroxyimino)-5-methyl-3-phenyl-2,3-dihydrofuro
d 10.36 (s, C]NeOH, (Z) isomer, 1H), 10.01 (s, C]NeOH, (E) isomer,
[3,2-c]quinolin-4(5H)-one (15a). White solid; mp: 140e142 ꢀC. FT-
1H,), 7.89e7.87 (m, (E) isomer and (Z) isomer, 2H), 7.75e7.71 (m, (E)
isomer and (Z) isomer, 2H), 7.40e7.37 (m, (E) isomer and (Z) isomer,
2H), 7.25e7.17 (m, (E) isomer and (Z) isomer, 4H), 6.99e6.86 (m, (E)
isomer and (Z) isomer, 4H), 5.48 (s, (E) isomer,1H), 5.40 (s, (Z) isomer,
1H), 3.66 (s, (Z) isomer, 3H), 3.62 (s, (E) isomer, 3H), 3.55 (s, (Z)
isomer, 3H), 3.52 (s, (E) isomer, 3H). 13C NMR (100 MHz, DMSO-d6)
IR (KBr)
(400 MHz, DMSO-d6)
n
/cmꢃ1 3431, 1685, 1602, 1551, 1335, 1135. 1H NMR
d
10.32 (s, C]NeOH, (E) isomer, 1H), 7.88 (d,
J¼6.4 Hz, 1H), 7.75 (t, J¼7.2 Hz, 1H), 7.63 (d, J¼8.0 Hz, 1H), 7.40 (t,
J¼7.2 Hz, 1H), 7.28e7.21 (m, 5H), 5.40 (s, 1H), 3.55 (s, 3H). 13C NMR
(100 MHz, DMSO-d6)
d 165.0, 158.3, 157.9, 140.2, 136.0, 132.1, 128.2,
128.0, 126.9, 122.4, 122.2, 115.5, 111.7, 110.1, 46.1, 28.8. MS (EI): (m/z)
(relative intensity) 306 (Mþ, 100), 289 (35), 248 (22). HRMS (EI):
calcd for C18H14N2O4 (M)þ 306.1004, found 306.1006.
d 165.3, 158.5, 158.0, 157.8, 157.0, 156.9, 140.2, 135.0, 134.9, 131.8,
131.6, 128.6, 128.3, 127.6, 125.0, 124.6, 122.2, 122.1, 120.4, 120.1, 115.4,
115.4, 111.8, 111.4, 110.2, 55.9, 55.8, 55.6, 28.8, 28.7, 28.6. MS (EI): (m/
z) (relative intensity) 336 (Mþ, 22), 320 (100), 288 (35), 262 (28).
HRMS (EI): calcd for C19H16N2O4 (MþH)þ 336.1105, found 336.1104.
4.4.17. (E)-2-(Hydroxyimino)-5-methyl-3-p-tolyl-2,3-dihydrofuro
[3,2-c]quinolin-4(5H)-one (15b). White solid; mp: 165e167 ꢀC. FT-
IR (KBr)
(400 MHz, DMSO-d6)
J¼6.8 Hz, 1H), 7.77e7.75 (m, 1H), 7.63 (d, J¼8.6 Hz, 1H), 7.39 (t,
n
/cmꢃ1 3438, 1687, 1630, 1556, 1335, 1125. 1H NMR
4.4.22. 2-(Hydroxyimino)-5-methyl-3-(naphthalen-2-yl)-2,3-dihy-
d
10.28 (s, C]NeOH, (E) isomer, 1H), 7.87 (d,
drofuro[3,2-c]quinolin-4(5H)-one (15g). White solid; FT-IR (KBr)
n/
cmꢃ1 3422, 1670, 1638, 1548, 1419, 1320. 1H NMR (400 MHz, DMSO-