3-AmiAnoC-5C'-flEuoProT-2E'-DoxoMspiAroN[beUnzSoC[f]RchIrPomTene-1,3'-indoline]-2-carbonitrile (4i): m.p.=
286-288, FT-IR (neat) ν = 3334, 2190, 1709, 1623, 1514, 1463, 1209, 746 cm-1.; 1H NMR
(DMSO-d6, 400 MHz): δ = 7.127 (2H, s, NH2), 7.053 (9H, m, Ar), 9.750 (1H, s, NH)
ppm.; 13C NMR (DMSO-d6, 100 Mz): δ = 50.76, 57.74, 111.67, 117.63, 118.29, 123.10,
123.30, 124.78, 125.38, 126.45, 126.58, 127.93, 128.01, 128.19, 131.59, 135.06, 148.41,
155.75, 159.86, 178.99 ppm.
Ethyl 2'-amino-3'-cyano-5-fluoro-6'-methyl-2-oxospiro[indoline-3,4'-pyran]-5'-carboxylate
(4j): m.p. =254-256, FT-IR (neat) ν = 3372, 3301, 3188, 2196, 1722, 1606, 1473, 1287,
1
1213, 1074, 751 cm-1.; H NMR (DMSO-d6, 400 MHz): δ = 0.794 (3H, t, J = 7.2 Hz,
CH3), 2.328 (s, 3H, CH3), 3.768 (2H, m, OCH2), 6.763-7.016 (3H, m, Ar-H), 7.303 (2H, s,
NH2), 10.436 (1H, s, NH) ppm.; 13C NMR (DMSO-d6, 100 Mz): δ = 13.45, 19.03, 49.42,
56.96, 60.72, 105.11, 109.78, 117.97, 122.32, 123.86, 129.01, 135.01, 142.62, 158.98,
159.40, 164.97, 179.05 ppm.
2'-Amino-5-fluoro-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-
carbonitrile (4k): m.p. =306-308; FT-IR (neat) ν = 3357, 3289, 3204, 2202, 1734, 1709,
1
1484, 1360, 1177, 771 cm-1.; H NMR (DMSO-d6, 400 MHz): δ = 6.865 (1H, dd, J= 4.4
Hz, Ar-H), 7.068 (1H, td, J1 = 8.4 Hz, J2 = 2.8 Hz), 7.280 (1H, dd, J = 2.8 Hz), 7.525 (1H,
d, J=8.4), 7.571 (1H, t, J=8), 7.746 (2H, s, NH2), 7.797 (1H, td, J1 = 8.4 Hz, J2 = 2.8 Hz),
7.965 (1H, d, J=8.4), 10.723 (1H, s, NH) ppm.; 13C NMR (DMSO-d6, 100 Mz): δ = 48.57,
57.01, 101.38, 110.65, 110.73, 112.55, 112.80, 113.03, 115.55, 115.79, 117.17, 117.38,
123.20, 125.49, 134.20, 135.13, 135.22, 138.90, 152.58, 155.81, 157.66, 158.87, 159.01,
160.01, 177.72 ppm.
2'-Amino-2,5'-dioxo-5',6',7',8'-tetrahydro-2H-spiro[acenaphthylene-1,4'-chromene]-3'-
carbonitrile (4m): m.p. =244-246; FT-IR (neat) ν = 3374, 3323, 3205, 2192, 1722, 1676,
1
1598, 1350, 1213, 997, 785 cm-1.; H NMR (DMSO-d6, 400 MHz): δ = 1.953 (2H, m,
CH2), 2.253 (2H, m, CH2), 2.644 (2H, m, CH2), 7.338 (2H, s, NH2), 7.429 (1H, d, J= 6.8
), 7.671 (1H, t, J=7.2), 7.846 (1H, t, J=7.2), 7.957 (2H, m), 8.280 (1H, d, J= 8) ppm.; 13C
NMR (DMSO-d6, 100 Mz): δ = 20.30, 27.20, 36.54, 51.50, 58.55, 113.59, 118.02, 120.50,
121.84, 124.98, 128.93, 129.36, 130.24, 131.89, 132.72, 140.92, 143.86, 159.12, 166.95,
195.89, 204.08 ppm.
4,4'-(1,3-Phenylene)bis(2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile)
(4r): m.p.=260-262 °C, FT-IR (neat) ν = 3436, 3330, 3180, 2964, 2196, 1653, 1600, 1365,
1213, 1150, 1030 cm-1., 1H NMR (DMSO-d6, 400 MHz): δ = 1.87-2.62 (12H, m), 4 (2H,
s), 6 (1H, s, Ar), 6.9 (4H, s, NH) ppm, 7.00 (2H, dd, J1= 7.6 Hz, J2 = 1.6 Hz), 7.2 (1H, t,
J= 7.6, Ar) ppm.; 13C NMR (DMSO-d6, 100 MHz): δ = 19, 30, 36.1, 39.7, 60.6, 115, 120,
125, 126, 129, 146, 159, 163, 196 ppm.
H2N
NC
O
O
O
CN
O
NH2