Novel 1-aminomethylisatins: Peculiarities of the synthesis and the reaction with tris(diethylamino)phosphine

Article abstract of DOI:10.1002/jhet.2011

The Mannich reaction of isatin with different primary and secondary amines and effect of the substituent in aromatic amines on the reaction pathway is studied. The efficient high-yield synthesis of novel isoindigo derivatives by the mild deoxygenation rea

Full text of DOI:10.1002/jhet.2011

July 2014
Novel 1-Aminomethylisatins: Peculiarities of the Synthesis and the
Reaction with Tris(diethylamino)phosphine
1027
*
Andrei V. Bogdanov, Lenar I. Musin, Anton V. Il’in, and Vladimir F. Mironov
A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Centre, Russian Academy of Sciences,
420088, Arbuzov Street, 8, Kazan, Russian Federation
*
E-mail: abogdanov@inbox.ru
Received January 9, 2013
DOI 10.1002/jhet.2011
Published online 16 December 2013 in Wiley Online Library (wileyonlinelibrary.com).
The Mannich reaction of isatin with different primary and secondary amines and effect of the substitu-
ent in aromatic amines on the reaction pathway is studied. The efficient high-yield synthesis of novel
isoindigo derivatives by the mild deoxygenation reaction of the corresponding isatins with tris
(diethylamino)phosphine is described.
J. Heterocyclic Chem., 51, 1027 (2014).
INTRODUCTION
recently n-heptylamine, n-dodecylamine, and some para-
substituted anilines used in this reaction result in corre-
sponding aminomethylisatins bearing secondary amine
function with medium yields [25]. At the same time,
three-component reaction of isatin with methylamine in
the presence of formaldehyde due to the absence of sterical
hindrances and strong nucleophilicity of amine nitrogen
does not stop on the stage of secondary amine formation
but further proceeds to give corresponding bisisatin [26].
As part of ongoing interest in the field of deoxygenation
reaction of a-dicarbonyl compounds under the action of
trivalent phosphorus derivatives earlier, we have studied the
reactions of acenaphthenequinone [27], certain alkylisatins,
aminomethylisatins, and tosylisatins with tris(diethylamino)
phosphine [28–32]. Those reactions are characterized by
mild conditions and allow to obtain different isoindigo deriv-
atives with high yields. The probable intermediate carbene
formation was confirmed by trapping them with fullerene
С60 to form corresponding methanofullerenes with moderate
yields [33–35].
Isatin and its derivatives play an important role in organic
chemistry and in particularly in the chemistry of biologically
active compounds. It was found that numerous heterocycles
containing isatin moiety can be used as an effective drug
against epilepsy, tuberculosis, bulimia, and so on [1–4].
1-Aminomethylisatins (so-called isatin-N-Mannich bases)
rank a special place among such compounds [5,6]. Thus,
1-morpholinomethylisatins and 1-piperidinomethylisatins
possess high activity towards certain Gram-negative bac-
teria [7]. In recent time, many research groups focus their
studies on the synthesis of conjugates of isatin derivatives
with different pharmacophore such as thiolactomycine and
fluoroquinolones (ciprofloxacin, norfloxacin, gatifloxacin,
etc.) [8–12]. Mannich reaction seems to be the most
convenient tool for this purpose.
Substituted isatins are also widely used in obtaining of
numerous nitrogen-containing heterocycles, in particular in
the synthesis of isoindigo derivatives [13–15]. These bisindole
compounds were found to have anticancer, antimicrobial, and
anti-inflammatory activity [16–21]. So, Natura (1-(b-D-tri-О-
acetylxylopyranosyl)-isoindigo) [22,23] and Meisoindigo
(1-methylisoindigo) [24] have been effectively used in the
treatment of chronic myelogenous leukemia. (Fig. 1).
Most works by the investigation of aminomethylation of
isatin by Mannich reaction describe the utilization of
secondary amine as the third component. As for the
primary amines, such works are very limited. For example,
Here, we disclose some peculiarities of the synthesis of
novel isatin-N-Mannich bases bearing secondary or tertiary
nitrogen atom in substituent and investigation of their reac-
tion with hexaethylphosphorous triamide (HEPTA).
RESULTS AND DISCUSSION
On the first stage of the study, the primary anilines—o-
toluidine and p-butylaniline—were used in the Mannich
© 2013 HeteroCorporation

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A. V. Bogdanov, L. I. Musin, A. V. Il'in, and V. F. Mironov
Vol 51
to the Mannich reaction with the participation of isatin,
secondary amines with acetal and pyrimidine fragments
were involved for the first time (Scheme 4).
In continuation of the study of the reaction of isatin
derivatives with trivalent phosphorus nucleophiles, com-
pounds 2, 3, 6, and 7 were treated with HEPTA under the
conditions reported earlier (ꢀ60ꢁС, CH2Cl2) [28–32]. The
evidence of the HEPTA oxidation to the corresponding
phosphate O = P(NEt2)3 was achieved by 31Р–{1Н} NMR
spectroscopy. The symmetrically substituted isoindigo
derivatives 8–10 with 70–90% yields were obtained as a
result of this reaction (Scheme 5). Their antifungal and
antibacterial activities are under investigation.
Figure 1. Representatives of biologically active isoindigo derivatives.
reaction with isatin that results in novel 1-
aminomethylisatins 2 and 3 with 87 and 48% yield,
respectively (Scheme 1).
The structure and composition of compounds 2 and 3 were
established on the basis of the NMR and IR spectroscopy and
elemental analysis data. Thus, there are broadened absorp-
tion band at 3308–3440 cmꢀ1, corresponding to NH group
and strong bands at 1610 and 1730 cmꢀ1, characteristic to
carbonyl fragment, and the 13С NMR spectra of compound
3 contain signals at 158.30 and 183.32 ppm corresponding
to amide and ketone carbonyls, respectively.
CONCLUSIONS
The Mannich reaction of isatin with various primary or
secondary amines was studied. It was established that
electron-withdrawing substituent in anilines does not allow
to obtain desired 1-aminomethylisatins.
It was shown that 4-aminobenzofurazane reacts with
formaldehyde in the presence of isatin with the formation
of only corresponding diaminomethane.
It was found that the possibility of this reaction strongly
depends on electronic structure of the substituent in
starting primary amine molecule. Thus, it was found that
the presence of electron-withdrawing substituent in
benzene fragment of aniline hinders the formation of the
desired products. In all cases, starting isatin and the corre-
sponding aniline were recovered even after the prolonged
heating of isatin, paraformaldehyde, and amine mixture
(Scheme 2).
A
mild-yield and high-yield synthesis of novel
bisaminomethylisoindigos was described.
Scheme 3. Preparation of diaminomethane 5.
Investigating the influence of structure of amine compo-
nent in Mannich aminomethylation, 4-aminobenzofurazane
was used. It has been shown for the first time that the interac-
tion of isatin, paraformaldehyde, and furazane 4 in equimolar
ratio at room temperature in ethanol leads to the formation of
corresponding diaminomethane 5 (Scheme 3). It should be
noted that the close synthetic result was reported in the
reaction of saccharine with paraformaldehyde [36]. But, that
reaction proceeded only in acidic conditions.
Scheme 4. Preparation of secondary aminomethylisatins 6 and 7.
Furthermore on the basis of isatin scaffold, novel 1-
aminomethyl derivatives 6 and 7 were obtained. Meanwhile
Scheme 1. Preparation of N-Mannich isatins 2 and 3.
Scheme 5. Synthesis of bis(aminomethyl)isoindigos 8–11.
Scheme 2. Effect of electron-withdrawing substituents.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

July 2014
Mannich Aminomethylation of Isatin
1029
1-(((2,2-Dimethoxyethyl)(methyl)amino)methyl)isatin (6). This
compound was obtained as bright orange powder; yield 80%;
mp: 86–87ꢁС; 1Н NMR (СDCl3): d 2.34 (s, 3Н, CH3), 2.65
(d, J = 5.2 Hz, 2Н, CH2), 3.28 (s, 6Н, CH3), 4.43 (t, J = 5.2 Hz,
1Н, CH), 4.45 (s, 2Н, CH2), 7.04 (dd, J = 7.5 Hz, J = 7.5 Hz,
1Н), 7.12 (d, J = 7.9 Hz, 1Н), 7.49 (dd, J = 7.5 Hz, J = 1.3 Hz,
1Н), 7.52 (dt, J = 7.9 Hz, J = 1.3 Hz, 1Н); 13C NMR (СDCl3): d
40.90 (СH3), 53.57 (СH3), 56.22 (СH2), 62.26 (СH2), 102.81,
111.92, 117.30, 123.52, 124.73, 138.20, 151.34, 158.58 (СO),
183.16 (СO); IR (nujol) n: 1740, 1698, 1605, 1326, 1291,
1243, 1129, 1075, 765 cmꢀ1; MS (EI) m/z: 278.1 [M+]. Anal.
Calcd for С14Н18N2O4: C, 60.20; H, 6.47; N, 9.85; found: C,
EXPERIMENTAL
All melting points were measured with a Stuart digital SMP10
apparatus (Bibby Scientific Ltd., UK). Solvents were distilled and
dried by standard literature procedures prior to use. Elemental
analyses for C, H, and N were performed using a CHNS-3 ana-
lyzer (EuroVector S.p.A., Italy). IR spectra were measured with
Bruker Vector-22 spectrometer (Bruker Corporation, Germany)
as suspensions in nujol. The 1H and 13C NMR spectra were
recorded on a Bruker Avance-400 instrument (Bruker Corpora-
1
tion, Germany) (400 MHz for H and 100.6 MHz for 13C), and
31P NMR spectra were recorded on a Bruker CXP-100 (Bruker
Corporation, Germany) (36.48 MHz).
60.42; H, 6.52; N, 10.07.
N,N0-Di(benzo[c][1,2,5]oxadiazol-4-yl)methanediamine
1-((4-(Pyrimidin-2-yl)piperazin-1-yl)methyl)isatin (7). This
compound was obtained as bright orange powder, yield 65%; mp:
180ꢁС; 1Н NMR (СDCl3): d 2.69 (dd, J = 5.0 Hz, J = 5.1 Hz, 4H,
2CH2), 3.84 (dd, J = 5.0 Hz, J = 5.1 Hz, 4H, 2CH2), 4.52 (s, 2H,
CH2), 6.48 (t, J = 4.8 Hz, 1H), 7.12 (d, J = 7.9 Hz, 1H), 7.14 (dd,
J = 7.5 Hz, J = 7.6 Hz, 1H), 7.61 (dt, J = 7.9 Hz, J = 1.3 Hz, 1H),
7.62 (dd, J = 7.4 Hz, J = 1.3 Hz, 1H), 8.28 (d, J = 4.8 Hz, 2H);
13C NMR (СDCl3): d 43.41 (СH2), 50.58 (СH2), 62.49 (СH2),
110.05, 111.70, 117.61, 123.89, 125.26, 138.32, 151.52,
157.68, 158.83, 161.52 (СO), 183.05 (СO); IR (nujol) n: 1750,
1732, 1606, 1591, 1303, 1268 cmꢀ1; MS (EI) m/z: 323.1 [M+].
Anal. Calcd for С17Н17N5O2: C, 60.95; H, 5.21; N, 21.39;
found: C, 63.15; H, 5.30; N, 21.66.
General procedure for the synthesis of isoindigo derivatives
8–11. To a solution of appropriate isatin derivative (2.64 mmol)
in dichloromethane (10mL), a solution of HEPTA (0.69 mL,
2.64mmol) in the same solvent (3 mL) was added dropwise at
ꢀ60ꢁС with bubbling of dry argon for 2 min. The reaction
mixture was then allowed to warm to room temperature. The
precipitate that formed was filtered off, washed with dry hexane,
and dried in vacuo (12Torr) to give the pure products. If the
aforementioned procedure does not give any solids, reaction
mixture was evaporated in vacuo (12 Torr) to dryness, and the
resulted residue was treated with dry pentane (10 mL) to give
(5).
To the suspension of isatin (1, 1.47g, 10mmol) in
absolute ethanol (10 mL) at 10ꢁC under constant vigorous
stirring, formaldehyde (37% aqueous solution, 10 mmol) was
added followed by the addition of the solution of
4-amonobenzofurazane (4, 1,35 g, 10mmol) in the same solvent
(5mL). Then, stirring was continued at room temperature for
1 h, a precipitate that formed was filtered off, washed with
pentane, and dried in vacuo (12 Torr) to give 2.68 g (95%) of
5 as yellow powder, mp: 181–184ꢁС; 1Н NMR (DMSO-d6):
d 4.90 (t, J = 5.4 Hz, 2H, СН2), 6.74 (d, J = 7.1 Hz, 2Н), 7.07
(d, J = 8.9 Hz, 2H), 7.39 (dd, J = 8.9 Hz, J = 7.1 Hz, 2H), 7.86
(t, J = 5.4 Hz, 2H, NH). 13C NMR (DMSO-d6): d 52.14
(СН2), 101.38, 103.06, 135.46, 135.53, 145.08, 150.21; IR
(nujol) n: 1621, 1573, 1408, 1388, 1298, 1149, 1010,
737 cmꢀ1
;
MS (EI) m/z: 282.1 [M+]. Anal. Calcd for
С13Н10N6O2: C, 55.32; H, 3.57; N, 29.77; found: C, 55.27;
H, 3.45; N, 29.59.
General procedure for the synthesis of substituted
aminomethylisatins 2, 3, 6, and 7. To the suspension of isatin
(1, 1.47 g, 10mmol) in absolute ethanol (10 mL) at 10ꢁC under
constant vigorous stirring, formaldehyde (37% aqueous solution,
10mmol) was added. After this, an appropriate amine (10 mmol)
was also added dropwise (solid amines was previously dissolved
in 5 mL of the same solvent) followed by additional stirring at
room temperature for 1 h. A precipitate that formed was filtered
off, washed with pentane, and dried in vacuo (12 Torr).
precipitate, which was separated as described earlier.
1,10-Bis((o-tolylamino)methyl)-1H,10H-[3,30]biindolylidene-
2,20-dione (8). This compound was obtained as dark-red solid,
yield 87%; mp: 178ꢁС (dec); 1Н NMR (DMSO-d6): d 2.09 (s, 3Н,
CH3), 5.26 (d, J = 6.1 Hz, 2Н, CH2), 6.08 (t, J = 6.3 Hz, 1H, NH),
6.5 (t, J = 7.3 Hz, J = 1.0 Hz, 1H), 6.85-6.94 (m, 3Н), 7.08 (m,
J = 7.5 Hz, J = 1.0 Hz, 1H), 7.44 (m, J = 7.6 Hz, J = 7.7 Hz,
J = 1.1 Hz, 1H), 7.6 (d, J = 7.9 Hz, 1H), 9.06 (dd, J = 8.0 Hz,
J = 0.7 Hz, 1H); 13C NMR (DMSO-d6): d 17.63 (СН3), 49.09
(СН2), 109.79, 110.1, 116.95, 120.7, 121.7, 121.9, 126.68,
128.8, 130.09, 132.62, 133.03, 143.42, 143.89, 166.92 (СO); IR
(nujol) n: 3429, 1702, 1608, 1520, 1400, 1255, 1236 cmꢀ1; MS
(EI) m/z: 500.2 [M+]. Anal. Calcd for С32Н28N4O2: C, 76.78, H,
5.64; N, 11.09; found: C, 76.55; H, 5.72; N, 11.15.
1-((о-Tolylamino)methyl)isatin (2).
This compound was
obtained as bright orange powder, yield 87%, mp: 194ꢁС; TLC:
1
Rf 0.62 (hexane/EtOAc 3:1); Н NMR (СDCl3): d 1.57 (s, 3Н),
5.3 (s, 2Н), 6.7 (t, J = 7.0 Hz, 1Н), 6.93 (d, J = 7.85 Hz, 1Н),
7.04-7.15 (m, 4Н), 7.58 (m, 1Н), 7.6 (m, 1Н); IR (nujol) n:
3440, 1731, 1607 cmꢀ1. Anal. Calcd for C17H17N2O2: C, 72.58;
H, 6.09; N, 9.96; found: C, 72.40; H, 6.02; N, 10.18.
1-((4-Butylphenylamino)methyl)isatin (3). This compound
was obtained as yellow powder, yield 78%; mp: 143–144ꢁС
(from ethanol); 1Н NMR (СDCl3): d 0.89 (t, J = 7.3 Hz, 3Н, CH3),
1.31 (m, 2Н, CH2), 1.52 (m, 2Н, CH2), 2.48 (d, J = 7.6 Hz, 2H,
CH2), 4.44 (s, 1H, NН), 5.22 (s, 2Н, CH2), 6.74 (d, J = 8.3, 2H),
7.01 (d, J = 8.3 Hz, 2H), 7.08 (d, J = 7.5 Hz, 1H), 7.10 (t,
J = 7.5 Hz, 1H), 7.57 (t, J = 8.7 Hz, 1H), 7.58 (d, J = 7.7 Hz, 1H);
13C NMR (СDCl3): d 13.89 (СH3), 22.24 (СH2), 33.77 (СH2),
34.63 (СH2), 50.98 (NСH2), 110.90, 113.95, 117.82, 123.88,
125.52, 129.41, 134.21, 138.19, 142.22, 150.42, 158.30 (СO),
183.32 (СO); IR (nujol) n: 3392, 1728, 1616, 1532, 1377, 1255,
1209, 1109, 1060, 755cmꢀ1; MS (EI) m/z: 308.2 [M+]. Anal.
Calcd for С19Н20N2O2: C, 74.00; H, 6.54; N, 9.08; found: C,
73.80; H, 6.32; N, 8.90.
1,10-Bis(4-butylphenylaminomethyl)-1H,10H-[3,30]biindolylidene-
2,20-dione (9). This compound was obtained as dark-red solid,
1
yield 86%; mp: 218ꢁС; Н NMR (СDCl3): d 0.89 (t, J = 7.2 Hz,
3H, СH3), 1.30 (m, 2Н, СH2), 1.52 (m, 2Н, СH2), 2.47 (m, 2Н,
СH2), 4.43 (br. s, NН), 5.24 (br. s, 2Н, СH2), 6.76 (d, J = 8.4 Hz,
2H), 6.93 (d, J = 7.6 Hz, 1H), 6.99 (d, J = 8.4 Hz, 2H), 7.07 (m,
J = 7.7Hz, J = 7.7 Hz, J = 1.0 Hz, 1H), 7.36 (m, J = 7.6 Hz,
J = 7.7Hz, J = 1.2 Hz, 1H), 9.12 (d, J = 7.7 Hz, 1H); 13C NMR
(СDCl3): d 13.91 (СH3), 22.26 (СH2), 33.80 (СH2), 34.68 (СH2),
50.84 (СH2), 108.26, 114.14, 121.80, 122.47, 129.28, 129.89,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

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A. V. Bogdanov, L. I. Musin, A. V. Il'in, and V. F. Mironov
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132.40, 133.59, 133.80, 142.88, 144.04, 168.15 (СO); IR (nujol) n:
3408, 1685, 1608, 1524, 1254, 1199, 1102, 1050, 1026 cmꢀ1; MS
(EI) m/z: 577.3 [M+]. Anal. Calcd for С38Н40N2O4: C, 77.87; H,
6.72; N, 9.41; found: C, 78.05; H, 6.89; N, 9.58.
1,10-Bis(((2,2-dimethoxyethyl)methylamino)methyl)-1H,10H-
[3,30]biindolylidene-2,20-dione (10).
This compound was
obtained as dark-red solid, yield 80%; mp: 70ꢁС; 1Н NMR
(СDCl3): d 2.44 (s, 3Н, CH3), 2.77 (d, J = 5.3 Hz, 2H, CH2),
3.37 (s, 6Н, 2CH3), 4.53 (m, 1Н), 4.60 (s, 2H, CH2), 7.05 (m,
J = 7.4 Hz, 1H), 7.06 (d, J = 7.8 Hz, 1H), 7.35 (m, J = 7.6 Hz,
J = 7.7 Hz, 1H), 9.12 (d, J = 7.6 Hz, 1H); IR (nujol) n: 1744,
1694 1609, 1298, 1074, 1025 cmꢀ1; MS (EI) m/z: 524 [M+].
Anal. Calcd for С28Н36N4O6 :C, 64.10; H, 6.92; N, 10.68;
found: C, 63.89; H, 6.78; N, 10.49.
1,10-Bis((4-(pyrimidin-2-yl)piperazin-1-yl)methyl)-1H,10H-
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[3,30]biindolylidene-2,20-dione (11).
This compound was
obtained as dark-red solid, yield 84%; mp: 218ꢁС; 1Н NMR
(СDCl3): d 2.72 (t, J = 5.0 Hz, J = 4.9 Hz, 4H, 2CH2), 3.83 (t,
J = 5.0 Hz, J = 4.9, 4H, 2CH2), 4.59 (s, 2Н, CH2), 6.45 (t, J = 4.7,
1H), 7.00 (d, J = 7.6 Hz, 1H), 7.07 (ddd, J = 7.7 Hz, J = 8.0 Hz,
J = 1.0 Hz, 1H), 7.36 (ddd, J = 7.7 Hz, J = 7.6 Hz, J = 1.0 Hz, 1H),
8.26 (d, J = 4.7 Hz, 2H), 9.09 (dd, J = 8.0 Hz, J = 0.7 Hz, 1H);
13C NMR (СDCl3): d 43.51, 50.71, 62.11, 109.25, 109.87,
121.51, 122.50, 129.64, 132.51, 133.36, 145.20, 157.66, 161.57,
168.76 (CO); IR (nujol) n: 1739, 1696, 1610, 1586, 1545, 1455,
1287, 1265, 1182, 1122, 1087, 1030 cmꢀ1. Anal. Calcd for
С34Н34N10O2 :C, 66.43; H, 5.58; N, 22.79; found: C, 66.39; H,
5.51; N, 22.73.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet