Synthesis of Novel Spiro[chromene-4,3'-indolines] and Spiro(indoline-3,4'-pyrano[3,2-h]quinolines)

Article abstract of DOI:10.1134/S1070428020020062

Abstract: The condensation of 1-alkylisatines with malononitrile and 8-hydroxyquinoline or 5,5-dimethyl-cyclohexane-1,3-dione in the presence of an aqueous solution of trimethylamine proceeds regioselectively as a one-pot three-component domino process to

Full text of DOI:10.1134/S1070428020020062

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 2, pp. 213–217. © Pleiades Publishing, Ltd., 2020.
Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 2, pp. 204–209.
Synthesis of Novel Spiro[chromene-4,3'-indolines]
and Spiro(indoline-3,4'-pyrano[3,2-h]quinolines)
S. A. Pogosyana,*, M. V. Pogosyanb, and A. A. Harutyunyana,c
a Scientific and Technological Center of Organic and Pharmaceutical Chemistry, NAS of Armenia, Yerevan, 0019 Armenia
b University of Cologne, Cologne, 50923 Germany
c Armenian–Russian University, Yerevan, 0051 Armenia
*e-mail: safar.poghosyan@gmail.com
Received July 30, 2019; revised December 13, 2019; accepted December 16, 2019
Abstract—The condensation of 1-alkylisatines with malononitrile and 8-hydroxyquinoline or 5,5-dimethyl-cyclo-
hexane-1,3-dione in the presence of an aqueous solution of trimethylamine proceeds regioselectively as a one-pot
three-component domino process to form spiro[chromene-4,3'-indoline] and spiro(indoline-3,4'-pyrano[3,2-h]-
quinoline).
Keywords: 1-alkylisatines, malononitrile, 8-hydroxyquinoline, 5,5-dimethylcyclohexane-1,3-dione, three-com-
ponent condensation, spiro(indoline-3,4'-pyrano [3,2-h]quinoline), spiro[chromene-4,3'-indoline]
DOI: 10.1134/S1070428020020062
Multicomponent reactions, which involve 1H-
Indole-2,3-dione (isatin) and occur as one-pot catalytic
domino processes, are the most common and efficient
methods of synthesis of spiro-fused heterocyclic com-
pounds [1].
nism to form spiro-fused 2-oxindoles: spiro(chromene-
4,3'-indoline) derivatives in the case of dimedone and
spiro(indoline-3,4'-pyrano[3,2-h]quinoline) derivatives
in the case of 8-hydroxyquinoline. The synthesized novel
spiro-fused compounds combine two different heterocy-
clic system comprising a carbocycle and three different
heterocycles, which determines the spectrum of their
biological activity.
The three-component reactions of isatin with malono-
nitrile or cyanoacetic ester, and compounds with an enolic
component or its synthetic equivalent in the structure were
used to obtain a great number of carbo- and heterocyclic
spirooxindoles, which are of interest for medical or com-
binatorial chemistry [2, 3].
The syntheses realized in the present work are pre-
sented in Scheme 1. The suggested mechanism of the
reaction is shown in Scheme 2.
As known, natural or synthetic oxindoles exhibit
diverse biological activities, including a wide range of
biological activity, including DNA-damaging [4], cyto-
toxic [5–7], fungicidal [8], antibacterial [9], and others.
The dielectrophile 2-(2-oxoindolin-3-ylidene)malo-
nonitrile (7) formed by the condensation of substituted
isatin 1 and malononitrile (2) undergoes a regioselective
Michael reaction with the participation of both electro-
philic centers (the cyano group and the β-position of the
activated double bond), leading to pyran ring closure; In
both cases, the enolic OH group attacks exclusively the
cyano group. The same reaction route was also suggested
for similar syntheses of spiro-fused isatin derivatives [2,
10–13].
Proceeding with our research into the synthesis of
spiro-fused isatins by base-catalyzed three-component
reactions [10, 11] and aiming at expanding the combi-
natorial potential of this synthetic approach, we involved
in such reactions 1-substituted isatins, malononitrile, and
5,5-dimethylhexane-1,3-dione (dimedone) or 8-hydroxy-
quinoline.
The IR spectra of the synthesized compounds con-
tain characteristic ν(NH2) bands at 3450–3150 cm–1,
ν(CN) bands at 2198–2190 cm–1, and ν(C=O) bands at
1714–1680 cm–1. The 13C NMR spectra of the products
containing a dimethylhexanone fragment display signals
It was shown that the one-pot three-component con-
densation of the mentioned compounds in ethanol in
the presence of an aqueous solution of trimethylamine
occurs in a regioselective fashion by a cascade mecha-
213

214
POGOSYAN et al.
Scheme 1.
O
O
NH2
CN
O
O
O
3
N
R
O
5a–5f
NMe3
N
+
CH2(CN)2
O
EtOH/H2O
OH
N
O
N
NH2
CN
R
1a–1f
2
4
O
N
R
6a–6e
1a–1f, 5a–5f, 6a–6e, R = H (a), CH3 (b), C2H5 (c), C3H8 (d), C4H9 (e), Bn (f); 5a–e, R = H (a), CH3 (b),
C2H5 (c), C3H7 (d), C4H9 (e), CH2C6H5 (f); 6a–6e, R = CH3 (a), C2H5 (b), C3H8 (c), C4H9 (d), CH2C6H5 (e).
1
at δC 31.6, 46.1, and 57.5 ppm assigned to the C(Me2)
carbon, quaternary spiro-oxindole carbon, and carbon
atoms linked to the CN group, respectively.
Avatar 330 instrument in mineral oil. The Н and 13C
NMR spectra were run on a Varian Mercury-300 VX spec-
trometer at 300 and 75.46 MHz, in DMSO-d6–CCl4 (1 : 3),
internal reference TMS. The elemental analyses were
obtained on a Eurovector ЕА 3000 analyzer. Thin-layer
chromatography was performed on Silufol UV-254 plates
in ethanol–benzene (2 : 5), visualization in iodine vapor.
To conclude, we would like to note that we still could
not establish the absolute configuration of the synthesized
3-spiroindolines; the same situation was mentioned in
some other publications concerning the synthesis of the
spiro-fused isatin derivatives [6, 14, 15].
Spiro[chromene-4,3'-indolines] 5a–5e and spiro-
(indoline-3,4'-pyrano[3,2-h]quinolines 6a–6e (gen-
eral procedure). A mixture of 20 mmol of isatine 1a–1f,
malononitrile (2), 5,5-dimethylcyclohexane-1,3-dione (3)
or 8-hydroxyquinoline (4) and 1 mL of aqueous trimeth-
ylamine in 80 mL of ethanol was stirred under reflux for
EXPERIMENTAL
Solvents were distilled before use and crystalline
substances were recrystallized from appropriate solvents.
The IR spectra were measured on a Thermo Nicolet
Scheme 2.
_
HO
N
C
O
N
O
C
NH
2
2
CN
O
O
O
N
N
R
N
R
R
1
7
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SYNTHESIS OF NOVEL SPIRO[CHROMENE-4,3'-INDOLINES]
215
2 h, after which 40 mL of the solution was distilled off,
and the remaining solution was left to stand in the cold.
The crystals that formed were filtered off and recrystal-
lized from ethanol.
3-carbonitrile (5d). Yield 5.2 g (69%), mp 248–247°C,
Rf 0.80. IR spectrum, ν, cm–1: 3276, 3162 (NH2), 2196
(CN), 1698, 1678 (C=O), 1633, 1609 (C=C). Н NMR
1
spectrum, δ, ppm: 1.02 t (3Н, CН3, J 7.4 Hz), 1.07 s (3Н,
CН3), 1.12 s (3H, CH3), 1.74 sextet (2H, CH2CH3, J
7.4 Hz), 2.07 d (1Н) and 2.18 d (1Н, CH2, J 16.0 Hz),
2.52 d (1Н) and 2.62 d (1H, CH2, J 17.6 Hz), 3.55–
3.73 m (2H, NCH2), 6.87 br.d (1H, C6Н4, J 7.6), 6.88 br.s
(2Н, NH2), 6.93 d.d.d (1H, C6H4, J 7.3, 7.3, 1.0 Hz),
6.98 d.d (1H, C6H4, J 7.3, 1.7 Hz), 7.21 d.d.d (1H, C6H4,
J 7.6, 7.3, 1.7 Hz). 13C NMR spectrum, δ, ppm: 11.1
(CH3 Pr), 20.0 (CH2), 27.1 (CH3), 27.8 (CH3), 31.6,
40.1 (CH2), 41.3 (CH2), 46.1, 49.8 (NCH2), 57.5 (CCN),
107.6 (CH), 110.8, 116.4 (CN), 121.6 (CH), 122.4 (CH),
127.7 (CH), 133.3, 142.9, 158.4, 163.1, 175.7, 193.3.
Found, %: C 70.12; Н 5.96; N 11.38. C22Н23N3O3. Cal-
culated, %: C 70.05; Н 6.14; N 11.13.
2-Amino-7,7-dimethyl-2',5-dioxo-5,6,7,8-
tetrahydrospiro[chromene-4,3'-indoline]-3-carboni-
trile (5a). Yield 5.5 g (82%), mp 280–282°C, Rf 0.24. IR
spectrum, ν, cm–1: 3368, 3246 (NH' NH2), 1686 (C=О),
1604-1590 (C=C). 1Н NMR spectrum, δ, ppm: 1.07 s and
1.12 s (6Н, Me2), 2.09 d and 2.19 d [2Н, 6,8-H(CH2), J
15.9 Hz], 2.52 d and 2.61 d [2Н, 6,8-H(CH2), J 17.6 Hz],
6.80–6.94 m (3Н) and 7.11 t.d (1Н, C6Н4, J 7.5, 1.5 Hz),
6.84 br.s (2Н, NH2), 10.26 s (1H, NH). Found, %: C
68.02; Н 5.15; N 12.53. C19Н17N3O3. Calculated, %: C
68.05; Н 5.11; N 12.53.
2-Amino-2,5'-dioxo-1',7,7-trimethyl-5,6,7,8-
tetrahydrospiro[chromene-4,3'-indoline]-3-carboni-
trile (5b). Yield 4.80 g (70%), mp 273–275°C. Rf 0.64.
IR spectrum, ν, cm–1: 3284, 3107 (NH2), 2192 (CN),
1701, 1682, 1666 (C=O), 1602 (C=C). 1Н NMR spectrum,
δ, ppm: 1.07 s and 1.12 s (6Н, Me2), 2.08 d and 2.16 d
[2Н, 6,8-H(CH2), J 16.0 Hz], 2.54 d and 2.61 d [2Н,
6,8-H(CH2), J 17.5 Hz], 3.20 s (3Н, NCH3), 6.87–7.01 m
(3H, C6Н4), 6.90 br.s (2Н, NH2), 7.23 d.d.d (1H, C6Н4, J
7.6, 6.9, 2.2 Hz). 13C NMR spectrum, δ, ppm: 25.9, 27.2,
27.7, 31.6, 40.1, 46.2, 49.9, 57.2, 107.5, 110.8, 116.5,
121.8, 122.2, 127.8, 133.2, 143.4, 158.5, 163.2, 175.9,
193.4. Found, %: C 68.72; Н 5.45; N 12.15. C20Н19N3O3.
Calculated, %: C 68.75; Н 5.48; N 12.03.
2-Amino-1'-butyl-7,7-dimethyl-2,5'-dioxo-5,6,7,8-
tetrahydrospiro[chromene-4,3'-indoline]-3-carboni-
trile (5e). Yield 5.7 g (73%), mp 247–248°C, Rf 0.80. IR
spectrum, ν, cm–1: 3360, 3288, 3149 (NH2), 2193 (CN),
1702, 1684, 1668 (C=O), 1603 (C=C). 1Н NMR spectrum,
δ, ppm: 1.00 t (3Н, CН3, J 7.3 Hz); 1.07 s (3Н, CН3), 1.13 s
(3H, CH3), 1.41–1.53 m (2H, CH2CH3), 1.64–1.75 m
(2H, CH2C2H5), 2.08 d (1Н, CH2, J 15.9 Hz), 2.19 d (1Н,
CH2, J 15.9 Hz), 2.52 d (1Н, CH2, J 17.6 Hz), 2.62 d (1H,
CH2, J 17.6 Hz), 3.58–3.76 m (2H, NCH2), 6.85 br.s (2H,
NH2), 6.85–7.00 m (3Н, C6Н4), 7.21 t.d (1Н, C6H4, J 7.5,
1.7 Hz). 13C NMR spectrum, δ, ppm: 13.4 (CH3), 19.5
(CH3), 27.2 (CH3), 27.8 (CH3), 28.7 (CH2), 31.6 (CMe2),
39.3 (CH2), 40.1 (CH2), 46.1 (Cspiro), 49.9 (CH2), 57.6
(CCN), 107.6 (CH), 110.8, 116.4, 121.5 (CH), 122.4
(CH), 127.7 (CH), 133.4, 142.8, 158.4, 163.1, 175.6,
193.3. Found, %: C 70.33; Н 6.28; N 10.95. C23Н25N3O3.
Calculated, %: C 70.57; Н 6.44; N 10.73.
2-Amino-7,7-dimethyl-2,5'-dioxo-1'-ethyl-5,6,7,8-
tetrahydrospiro[chromene-4,3'-indoline]-3-carboni-
trile (5c). Yield 3.62 g (50%), mp 278–280°C, Rf 0.73.
IR spectrum, ν, cm–1: 3271, 3157 (NH2), 2198 (CN),
1
1698, 1680 (C=O), 1634, 1611, 1602 (C=C). Н NMR
spectrum, δ, ppm: 1.07 s (3Н, CН3), 1.13 s (3Н, CН3),
1.28 t (3H, CH3, J 7.2 Hz), 2.08 d (1Н, CH2, J 16.0 Hz)
and 2.18 d (1Н, CH2, J 16.0 Hz), 2.53 d (1Н, CH2, J
17.6 Hz) and 2.62 d (1H, CH2, J 17.6 Hz), 3.74 q (2H,
NCH2, J 7.2 Hz), 6.86 br.s (2H, NH2), 6.88 br.d (1H, C6H4,
J 7.8 Hz), 6.94 t.d (1H, C6H4, J 7.3, 0.9 Hz), 6.98 d.d.d
(1H, C6H4, J 7.3, 1.7, 0.5 Hz), 7.22 d.d.d (1H, C6H4, J 7.7,
7.3, 1.7 Hz). 13C NMR spectrum, δ, ppm: 11.7, 27.1, 27.8,
31.6, 34.1, 40.1, 46.0, 49.8, 57.5, 107.5, 110.8, 116.4,
121.5, 122.4, 127.8, 133.4, 142.3, 158.4, 163.0, 175.3,
193.3. Found, %: C 69.62; Н 5.75; N 11.53. C21Н21N3O3.
Calculated, %: C 69.41; Н 5.82; N 11.56.
2-Amino-1'-benzyl-7,7-dimethyl-2,5'-dioxo-
5',6',7',8'-tetrahydrospiro[chromene-4,3'-indoline]-
3-carbonitrile (5f). Yield 5.4 g (64%), mp 248–247°C,
Rf 0.80. IR spectrum, ν, cm–1: 3380, 3320, 3206 (NH2),
1
2197 (CN), 1714, 1680, 1660 (C=O), 1601 (C=C). Н
NMR spectrum, δ, ppm: 1.10 s (3Н, CН3), 1.15 s (3H,
CH3), 2.14 d (1Н, CH2, J 15.9 Hz), 2.24 d (1Н, CH2, J
15.9 Hz), 2.57 d (1H, CH2, J 17.5 Hz), 2.66 d (1Н, CH2,
J 17.5 Hz), 4.90 d (1Н, NCH2, J 16.2 Hz), 4.97 d (1Н,
NCH2, J 16.2 Hz), 6.59 d (1Нarom, J 7.7 Hz), 6.91–7.12 m
(3Harom), 6.96 br.s (2H, NH2), 7.20–7.34 m (3Harom),
7.44–7.49 m (2Harom). 13C NMR spectrum, δ, ppm: 27.2
(CH3), 27.8 (CH3), 31.6 (CMe2), 40.1 (CH2), 43.4 (CH2),
2-Amino-7,7-dimethyl-2,5'-dioxo-1'-propyl-
5',6',7',8'-tetrahydrospiro[chromene-4,3'-indoline]-
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POGOSYAN et al.
46.3 (Cspiro), 49.8 (CH2), 57.4 (CCN), 108.5 (CH), 110.8,
116.8, 121.9 (CH), 122.3 (CH), 126.5 (CH), 126.6 (2CH),
127.6 (CH), 127.9 (2CH), 133.2, 135.6, 142.4, 158.5,
163.4, 176.1, 193.6. Found, %: C 73.44; Н 5.41; N 9.84.
C26Н23N3O3. Calculated, %: C 73.39; Н 5.45; N 9.88.
spectrum, ν, cm–1: 3360 (EtOH), 3288, 3149 (NH2), 2193
(CN), 1702, 1684, 1668 (C=O), 1603 (C=C). Н NMR
1
spectrum, δ, ppm: 0.99 t (3Н, CН3, J 7.3 Hz), 1.10 t (3H,
CH3, J 7.0 Hz), 1.38–1.50 m (2H, CH2CH3), 1.65–1.78 m
(2Н, CH2C2H5), 3.41–3.51 m (2H), 3.68–3.89 m (3H,
NCH2, OCH2, OH), 6.57 d (1Harom, J 8.7 Hz), 7.03–
7.16 m (3H, C6H4), 7.16 br.s (2H, NH2), 7.35 t.d (1H,
C6H4, J 7.6, 1.2 Hz), 7.47 d (1Нarom, J 8.7 Hz), 7.53 d.d
2'-Amino-1-methyl-2-oxospiro(indoline-3,4'-
pyrano[3,2-h]quinoline)-3'-carbonitrile (6a). Yield
4.6 g (65%), mp 355–357°C, Rf 0.64. IR spectrum,
ν, cm–1: 3416, 3301 (NH2), 2192 (CN), 1720, 1660 (C=O),
(1H, 8'-Hquinoline, J 8.3, 4.2 Hz), 8.20 d.d (1Н, 7'-Hquinoline
,
1
J 8.3, 1.6 Hz), 8.95 d.d (1H, 9'-Hquinoline, J 4.2, 1.6 Hz).
13C NMR spectrum, δ, ppm: 13.3, 18.1, 19.4, 28.9, 39.3,
50.3, 54.3, 56.0, 108.3, 117.5, 118.4, 121.8, 122.6, 123.3,
123.5, 124.7, 128.0, 128.8, 133.8, 135.3, 135.4, 137.7,
142.5, 144.2, 149.6, 161.0, 176.3. Found, %: C 72.58; Н
5.31; N 14.29. C24Н20N4O2. Calculated, %: C 72.71; Н
5.08; N14.13.
1600 (C=C). Н NMR spectrum, δ, ppm: 3.30 s (3Н,
NCH3), 6.59 d (1Н, C6H2, J 8.6 Hz), 7.05–7.15 m (3H,
C6H4), 7.20 br.s (2Н, NH2), 7.38 t.d (1Н, C6H4, J 7.6,
1.6 Hz), 7.48 d (1Н, C6H2, J 8.7 Hz), 7.54 d.d (1H,
8'-Hquinoline, J 8.3, 4.2 Hz), 8.22 d.d (1H, 7'-Hquinoline, J
8.3,1.6 Hz), 8.95 d.d (1Н, 9'-Hquinoline, J 4.2, 1.6 Hz).
Found, %: C 71.21; Н 3.87; N 15.65. C21 Н14N4O2. Cal-
culated, %: C 71.18; Н 3.98; N 15.81.
2'-Amino-1-benzyl-2-oxospiro(indoline-3,4'-
pyrano[3,2-h]quinoline)-3'-carbonitrile (6e). Yield
5.5 g (69%), mp 333–335°C, Rf 0.66. IR spectrum,
ν, cm–1: 3321, 3178 (NH2), 2192 (CN), 1696, 1656 (C=O),
1608 (C=C). 1Н NMR spectrum, δ, ppm: 4.95 and 5.04 d
2'-Amino-1-ethyl-2-oxospiro(indoline-3,4'-
pyrano[3,2-h]quinoline)-3'-carbonitrile (6b). Yield
4.5 g (61%), mp 318–321°C, Rf 0.61. IR spectrum,
ν, cm–1: 3408, 3122 (NH2), 2192 (CN), 1699, 1652 (C=O),
1
(1Н and 1H, CН2, J 15.7 Hz), 6.59 d (1H, 5'/6'-Hquinoline
,
1620 (C=C). Н NMR spectrum, δ, ppm: 1.30 t (3Н,
CН3, J 7.1 Hz), 3.76–3.89 m (2Н, CН2), 6.57 d (1Harom, J
8.7 Hz), 7.04–7.15 m (3Harom), 7.27 br.s (2H, NH2),
7.37 t.d (1H, C6H4, J 7.6, 1.4 Hz), 7.52 d (1Нarom, J
8.7 Hz), 7.58 d.d (1Hquinoline, J 8.3, 4.2 Hz), 8.26 d.d
(1Нquinoline, J 8.3, 1.6 Hz), 8.97 d.d (1Hquinoline, J 4.2,
1.6 Hz). Found, %: C 71.61; Н 4.16; N 15.05. C22Н16N4O2.
Calculated, %: C 71.73; Н 4.38; N 15.21.
J 8.6 Hz), 6.93 br.d (1H, 7-Hisatine, J 7.8 Hz), 7.05 d.d.d
(1H, 5-Hisatine, J 7.8, 7.4, 0.7 Hz), 7.16 d.d (1H, 4-Hisatine, J
7.4, 1.2 Hz), 7.22–7.41 m (8Н, Нarom, NH2, C6H5), 7.49 d
(1H, 5'/6'-Hquinoline, J 8.6 Hz), 7.55 d.d (1H, 8'-Hquinoline
,
J 8.3, 4.2 Hz), 8.23 d.d (1H, 7'-Hquinoline, J 8.3,1.7 Hz),
8.97 d.d (1H, 9'-Hquinoline, J 4.2, 1.7 Hz). Found, %: C
75.50; Н 4.13; N 13.34. C27Н18N4O2. Calculated, %: C
75.34; H 4.21; N 13.02.
2'-Amino-1-propyl-2-oxospiro(indoline-3,4'-
pyrano[3,2-h]quinoline)-3'-carbonitrile (6c). Yield
4.9 g (64%), mp 316–318°C, Rf 0.68. IR spectrum,
ν, cm–1: 3321, 3194 (NH2), 2192 (CN), 1716, 1660 (C=O),
1608 (C=C). 1Н NMR spectrum, δ, ppm: 1.00 t (3Н, CН3,
J 7.4 Hz), 1.71–1.84 m (2H, CH2CH3), 3.66–3.83 m (2Н,
NCН2), 6.58 d (1H, 5'-Hquinoline, J 8.6 Hz), 7.03–7.16 m
(3Harom), 7.19 br.s (2H, NH2), 7.35 t.d (1H, C6H4, J 7.6,
1.5 Hz), 7.48 d (1Н, 6'-Hquinoline, J 8.6 Hz), 7.54 d.d (1H,
8'-Hquinoline, J 8.2, 4.2 Hz), 8.21 d.d (1Н, 7'-Hquinoline, J
8.2, 1.5 Hz), 8.95 d.d (1H, 9'-Hquinoline, J 4.2, 1.5 Hz).
13C NMR spectrum, δ, ppm: 10.9, 20,2, 41.2, 50.4, 54.3,
108.5, 117.6, 118.5, 121.9, 122.7, 123.4, 123.6, 124.7,
128.1, 128.9, 133.7, 135.5, 137.6, 142.5, 144.2, 149.7,
161.0, 176.5. Found, %: C 72.16; Н 4.65; N 14.40.
C23Н18N4O2. Calculated, %: C 72.24; Н 4.74; N 14.65.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
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