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NITRATION OF 2,3- TRIMETHYLEN -3,4-DIHYDROQUINAZOLIN-4-ONES
AND QUINAZOLINES
Tukhsanov Feruz Sadullayevich ,
Assistant of the Department of Chemistry of the Uzbek-Finnish Pedagogical Institute,
Samarkand, E-mail:
Musulmonov Noryigit Hasanovich
Associate Professor of the Department of Chemistry of the Uzbek-Finnish Pedagogical Institute,
Samarkand, Uzbekistan. https://orcid.org/0000-0002-2092-3115
E - mail :
Abstract:
The nitration reactions of 2,3-polymethylene-3,4-dihydroquinazolin-4-one and
quinazolines were studied . The reaction conditions for the substitution of hydrogen atoms in
positions 6 and 8 of the aromatic ring were shown. It turned out that it is impossible to
introduce a second nitro group into the quinazoline ring without using an excess amount of the
nitrating mixture (1:4) and under relatively complex conditions (heating to 90-100 0C). The
synthesized compounds were studied for the first time and it was found that such organic
substances have biological activity. 2,3-Polymethylene-3,4-dihydroquinazolin-4-one was
nitrated under special conditions to obtain several different nitro derivatives and their properties
(reduction, substitution reactions) were studied. This nitration process was first carried out on
three-ring quinazoline and quinazoline rings, and their properties were studied.
Key words:
2,3-polymethylene-3,4-dihydroquinazolin-4-ones, ichinazolines , nitration,
amination , transamination , enamine , acetone cyanohydrin , bromination .
VISIONS
Previously [1,3] we studied some electrophilic substitution reactions of 2,3-
polymethylene-3,4-dihydroquinazolin-4 – ones . Some of the synthesized compounds have
growth-regulating , hypnotic, muscle-relaxing , narcotic action. Therefore, they are of certain
practical interest. On the other hand, the presence of several reaction centers (pyridine nitrogen
atom, aromatic ring, etc.) make them interesting in chemical terms. Before our research, there
are almost no data on nitration reactions of quinazalines in the literature . Therefore, the study
of these reactions is of great scientific interest.
Purpose of the work:
To date, there are no data in the literature on the electrophilic substitution of 2,3-
polymethylene-3,4-dihydroquinazolin-4-ones. There is only information on the nitration of the
simplest representative of the quinazoline series - quinasolone-4 and some of its derivatives. [1]
It was therefore of interest to investigate the nitration reactions of 2,3-polymethylene-3,4-
dihydroquinazolin-4-ones and quinazolines .
For this purpose, we studied [2,3,4,5] the nitration of 2,3-polymethylene-3,4-
dihydroquinazolin-4-ones (I-III). The reaction proceeds smoothly when I-III, IV are treated
with a nitrating mixture (reagent ratio 1:2.3) and leads to 6-nitro-2,3-polymethylene-3,4-
dihydroquinazolin-4-ones (V-XIII).
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N
C
C
N
O
(CH
2
)
n
N
C
C
N
O
2
N
O
(CH
2
)
n
I-III, IV
V-VIII
IV n= 1; IV -VI n=2; X, VII n=3; IV, VIII n=4
Compounds I-III, IV react with a mixture of nitric and sulfuric acids and give V-VIII
under mild conditions. However, it is not possible to introduce a second nitro group into the
quinazoline ring even when using an excess of the nitrating mixture (1:4.6) and under relatively
harsh conditions (heating to 90-100
0
).
The position of the nitro group of 6-nitro-2,3-polymethylene-3,4-dihydroquinazolin-4-
ones has been proven by spectral data, their counter synthesis from 5- nitroanthranilic acid, and
also by reduction with tin chloride to the corresponding 6-amino-2,3-polymethylene-3,4-
dihydroquinazolin-4-ones [XI]. The latter are reduced with zinc in hydrochloric acid at room
temperature and yield 6-amino-2,3-polymethylene-3,4-dihydroquinazolines XII.
N
C
C
N
O
2
N
O
(CH
2
)
n
V
N
C
C
N
H
2
N
O
(CH
2
)
n
XI
N
O
2
N
C
N
(CH
2
)
n
XII
The nitration reaction of 2,3-trimethylene-3,4-dihydroquinazoline (XIII) proceeds
differently. When using a 1:1 reagent ratio, a mono nitro product is formed – 6-nitro-2,3-
polymethylene-3,4-dihydroquinazoline (XIV), and at 1:2 – 6,8-dinitro-2,3-trimethylene-3,4-
dihydroquinazoline (XV).
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N
C
N
N
C
N
O
2
N
NO
2
N
C
N
O
2
N
XV
XIII
XIV
The possibility of introducing two nitro groups into the molecule of 2,3-trimethylene-
3,4-dihydroquinazoline is apparently explained by an increase in nucleophilicity benzene ring
during the transition from 2,3-trimethylene-3,4-dihydroquinazolone-4 to the corresponding
quinazoline , which is associated with the withdrawal of electrons from the aromatic ring by the
amide carbonyl .
Reduction of the nitro group of 6'-nitro-2,3-trimethylene-3,4-dihydroquinazoline gives
6'-amino-2,3-trimethylene-3,4-dihydroquinazoline, which is identical to the product obtained
from 6'-nitro-2,3-trimethylene-3,4-dihydroquinazolin-4-one.
In the mass spectrum of XIV there is an intense peak of the molecular ion with m/e
262(M
+
), 215(M
+
-47), 182(M
+
-80), 169(M
+
-93), 149(M
+
-113), 103(M
+
-159), the relative
intensity of which is 100, 25, 12, 54, 10, 9%, respectively.
In the PMR spectrum of compounds XIV and XV, the methylene protons at α-C, β-C, γ-
C have chemical shifts at 2.80; 2.10; 3.50 and 2.98; 2.10; 3.63 ppm , respectively, and the
protons of the methylene group at C-4 – at 4.55 and 4.73 ppm . The signals of the protons of the
aromatic ring appear in the region of 6.80 ppm (doublet, J=8.0 Hz , H-8), 7.78 ppm (doublet-
doublet, J
ortho
=12 Hz , J
meta
=2 Hz , H-7) and 8.70 ppm . (doublet, J
meta
= 2.5 Hz , H-5) for XIV,
and for XV – at 8.68 ppm (doublet, J = 2.5 Hz , H-5) and 7.98 ppm (doublet, J = 2 Hz , H-7).
(
ppm-millionth of a decimal fraction
).
Acylation of 6-amino-2,3-trimethylene-3,4-dihydroquinazolin-4-one and -quinazoline
with acetic anhydride or methyl chlorocarbonate leads to the corresponding acyl derivatives
( XVI a, b).
XV
N
C
N
H
2
N
X
+
(CH
3
CO)
2
O
ili
CH
3
C
O
Cl
N
C
N
RCOHN
X
XVI
a) R=CH
3
, X=O; b) R=OCH
3
, X=H
2
a
b
Table 1. Nitration products of 2,3-polymethylene-3,4-dihydroquinazolin-4-ones and
quinazolines .
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Re
ac
tio
n
pr
od
uc
t
n
R
Ex
it
%
M
.p
.
0
C
x
R
fx
x
Found
Gross
formula
Calculated
C H N
C
H
N
1
2
3
4
5
6
7 8 9 10
11
12
13
V
1
-
73
187-188
0.
78
57
.1
3.
9
18
.2
C
11
H
9
N
3
O
3
57.1 3.9 18.2
VI
2
-
54
179-180
0.
64
68
.6
4.
6
7.
0
C
12
H
11
N
3
O
3
58.8 4.5 17.1
VII
3
-
57
104-105
0.
64
60
.3
5.
2
16
.3
C13H13N3
O3
60.2 5.0 16.2
VIII
4
-
74
182-183
0.
94
61
.3
5.
2
15
.3
C14H15N3
O3
61.5 5.5 15.4
XI
1
-
90
248-249
0.
33
65
.8
5.
6
20
.6
C
11
H
11
N
3
O
65.7 5.5 20.9
XII
1
-
53
184-186
0.
12
70
.4
7.
1
26
.1
C
11
H
11
N
3
70.6 7.0 22.4
XIV
+
-
80
187-189
0.
46
60
.7
5.
3
19
.5
C
11
H
11
N
3
O
2
60.8 5.1 19.3
XV
+
-
88
214-216
0.
36
50
.4
3.
7
21
.7
C
11
H
10
N
4
O
4
50.4 3.8 21.4
XVI a +
C
H
3
95
265-266
0.
28
64
.4
5.
3
17
.1
C13H13N3
O2
64.2 50.
4
17.3
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16th
centur
y
+
O
C
H
3
88
113-115
0.
51
63
.9
6.
5
17
.3
C13H15N3
O2
63.7 6.1 17.1
* Note : Compounds I–IV, VI, VII, IX a-z , k-r, XV were recrystallized from acetone;
IX a-r from alcohol; XII, XIII from hexane ; XIV from acetone– hexane .
For compounds I, II, V– VIIIa , IXf , c-d, g, j, n-p, x, XV the Rf values were determined
in the solvent system chloroform–methanol 1:1, 10:1 ( silufol ); for XIII chloroform–
ether, 15:1 ( silufol ); IV–X chloroform (aluminum oxide); for III, VIII e, g –
chloroform–ether, 14:1 (aluminum oxide); for IX p, XII – chloroform–ether, 9:1
(aluminum oxide).
MATERIALS AND METHODS
Nitration of 2,3-polymethylene-3,4-dihydroquinazolin-4-ones and quinazolines was
carried out according to a modified procedure [6].
6-nitro-2,3-trimethylene-3,4-dihydroquinazolin-4-one(V). 5 g (26 mmol ) of 2,3-
trimethylene-3,4-dihydroquinazolin-4-one are dissolved in 10 ml of sulfuric acid (d=1.84) with
stirring and cooling to 0
°
C. A nitrating mixture consisting of 2.5 ml of nitric (d=1.5) and 3.5
ml of sulfuric acid (d=1.84) is added to the reaction mixture in portions with vigorous stirring at
such a rate that the temperature of the reaction mixture is below 2
°
C. The mixture is stirred for
1 hour at 5-10
°C
, for 1 hour at 20
°C
, poured into ice, the formed precipitate is filtered off and
thoroughly washed with water. Recrystallization from methanol gives 4.5 g of 6-nitro-2,3-
trimethylene-3,4-dihydroquinazolin-4-ones(V) with a mp of 187–188. A mixed melting point
with V, obtained by condensation of 5-nitroanthranilic acid with γ- butyrolactam , does not give
depression.
Similarly to the above, nitration of 2,3-tetra-, -penta-, hexamethylene-3,4-
dihydroquinazaline-4-ones was carried out.
6-nitro-2,3-trimethylene-3,4-dihydroquinazolin-4-one (XIV).
0.33 g (2 mmol ) of
2,3-trimethylene-3,4-dihydroquinazoline is dissolved with stirring and cooling to -2-5
0
C in 3
ml of concentrated sulfuric acid. A nitrating mixture consisting of 0.09 ml (2.14 mmol ) of
nitric acid (d = 1.5) and 0.2 ml of sulfuric acid (d = 1.84) is added to the reaction mixture in
portions with vigorous stirring at such a rate that the temperature of the reaction mixture is
below 0
0
C. Stir at this temperature for 30 minutes, at 5-10
0
C 1 hour and at 20
0
C for 1 hour,
pour into ice, alkalize with ammonia to pH = 8.9. The formed precipitate is filtered off, washed
with water, dried. Yield XIV 0.33 g, T ( melting point ) 187 – 189 (from methanol). IR
spectrum: 1620 ( υ
C = N
) cm
-1
, 1508 (υ
NO2
) cm
-1
, molecular weight 217 (mass spectrometry ).
6,8-dinitro-2,3-trimethylene-3,4-dihydroquinazoline(XV).
From 0.5 g (3 mmol ) of
2,3-trimethylene-3,4-dihydroquinazoline and a nitrating mixture consisting of 0.25 ml (6 mmol )
of nitric acid (d=1.5) and 0.36 ml of sulfuric acid (d=1.84) 0.56 g of XV are obtained.
T( melting point ) 214 – 216 (from methanol). IR spectrum: 1625 ( υ
C =N
) cm
-1
, 1520 (υ
NO2
)
cm
-1
, molecular weight 262 (mass spectrometry ).
6-amino-2,3-trimethylene-3,4-dihydroquinazolin-4-ones[XI]. A mixture of 1.2 g tin
chloride in 35 ml concentrated sulfuric acid is added
to a solution of 2 g (8.6 mmol ) V in
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200 ml alcohol with heating to 80-90
0
C and stirring. The reaction mixture is boiled for 3 hours,
cooled, and alkalized with 10% sodium hydroxide solution until a strongly alkaline medium is
obtained. Extracted with chloroform and dried with magnesium sulfate. The residue after
distilling off the solvent is recrystallized from ethyl acetate. Yield of XI 1.57 g, T( melting
point ) 248 – 249. IR spectrum: 1625 ( υ
C =N
) cm-
1
, 1665 ( υ
C =O
) cm
-1
, 3339 (υ
NH2
) cm
-1
molecular weight 201 (mass spectrometry ).
Synthesis of 6-amino-2,3-trimethylene-3,4-dihydroquinazoline[XII].
A mixture of 1
g (5 mmol ) of 6-nitro-2,3-trimethylene-3,4-dihydroquinazolin-4-one, 3 g of zinc dust in 30 ml
of hydrochloric acid (1:1) was stirred for 8 hours at room temperature. Excess zinc was filtered
off, washed with hot water, the filtrate was alkalized with ammonia and extracted with
chloroform. The residue after drying (sodium sulfate) and distillation of the solvent was
recrystallized from hexane . 0.49 g was obtained, T( melting point ) 184 – 186
0
C.
The restoration of IX was carried out in a similar manner to that described above.
6-acetamino-2,3-trimethylene-3,4-dihydroquinazolin-4-one[XVI].
1 g (5 mmol ) of
6-amino-2,3-trimethylene-3,4-dihydroquinazolin-4-one is dissolved in 10 ml of acetic
anhydride and heated for 1 hour at a temperature of 50–60
0
C. The precipitate that forms upon
cooling is filtered off, thoroughly washed with water and dried. Yield 1.15 g, T( melting point )
265–266
0
C (from alcohol).
6-Carbomethoxyamino-2,3-trimethylene-3,4-dihydroquinazoline
hydrochloride
[XVI].
To a solution of 0.45 g (2.4 mmol ) of 6-amino-2,3-trimethylene-3,4-dihydroquinazoline
in 8 ml of chloroform is added 0.4 ml (4.7 mmol ) of methyl chlorocarbonate. After 30 minutes,
the formed precipitate is filtered off, washed with ether, and dried. 0.6 g of the acid chloride is
obtained . T ( melting point ) 290
0
C ( decomp .).
Results and discussion
The synthesis of the target compounds is shown in Scheme 1. The starting material 2,3-
trimethylene-3,4-dihydroquinazoline (3) was prepared according to the described procedure [21]
by refluxing N- ( trimethoxybenzoyl )-3-methoxyanthranilic acid with acetic anhydride
followed by reaction with hydrazine to give the compound 33-amino-8-methoxy-2-
trimethoxyphenylquinazoline-4. The IR spectra of the compound showed absorption bands at
3221.35, 3387.83, and 1655.19 cm due to the stretching vibrations of the −1 NH 2 and CO
groups , respectively, and 1 H NMR resulted in the appearance of a singlet consisting of two
protons for the NH 2 group at 5.842.
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Compound 3 reacts with formamide to form 8-methoxy-2-trimethoxyphenylquinazolin-
4(3 H )-one (5), the latter compound shows a broadened band for CO at 1655.67 cm−1 and 1 H
NMR shows a singlet peak for NH group at 8.292 ppm . The compound reacts with ammonia to
form benzamide derivative 6, the IR spectrum of compound 6 shows broadened vibrational
bands for NH and NH at 3193.13, 3367.91 and 3389.62 and broadened bands at 1672.66 and
1663.23 for two CO groups. In addition, 1 H NMR data showed a singlet peak for NH group at
6.069 ppm . and a singlet peak for the NH fragment at 9.782 ppm . The compound reacts with
hydrazine hydrate in the presence of ethanol to form a hydrazide derivative . The compound
showed characteristic CO bands diamide at 1670.63 and 1655.19 and NH , NH . Absorption at
3376.45, 3382.21, 3175.43 and 3295.34 cm−1, in addition to a singlet H NMR peak at 4.479
ppm for NH and two singlets for NH diamide at 10.134 and 10.167 ppm . Compound 7 reacts
with benzenesulfonyl chloride to form a compound 83366.45, 3372.52 and 3385.43 cm−1 with
absorption bands of NH groups and a CO band at 1670.65 and 1655.37 cm−1 in the IR
spectrum, as well as singlets at 8.5497 and 12.615 ppm for NH protons .1 H NMR. In addition,
the compound reacts with 4-benzenesulfonyl chloride to form a compound. Singlet 1 H NMR
for NH at 11.885 ppm . due to CO and NH , respectively, around −1 with absorption lines at
1655.82 and 3385.56 cm. Furthermore, the compound reacts with methylamine to form 3-
methyl-8-methoxy-2-trimethoxyphenylquinazolin-4(3 H )-one (10), the latter compound being
confirmed by the presence of the CH group at 317.08 and 2.637 ppm by 13 C NMR and 1 H
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NMR, respectively. Compound 33 reacts with 4,5-trimethoxyaniline to form 3-(3,4,5-
trimethoxyphenyl)-8-methoxy-2-trimethoxyphenylquanazoline-4, which is confirmed by the
presence of separate peaks at 56.18, 59.56 and 60.23 ppm . and 3.624, 3.768 and 3.964 ppm ,
due to one methoxy group and two trimethoxy groups.
6-nitro-2,3-trimethylene-3,4-dihydroquinazolin-4-one (8) A mixture of equimolar
amounts of 3-aminoquinazoline derivative (4) and isatin (10 mmol ) in glacial acetic acid (5 ml)
was heated under reflux for 2 h, then poured into ice water. The resulting solid was filtered,
washed with water and recrystallized from ethanol to give methyl orange crystals; yield 75%;
mp 220–222°C; IR (cm−1): 3267 ( NH ), 3098-3067 ( CH aromatic), 2920 ( CH aromatic),
1720 ( C = O ), 1686 ( C = O ), 1612 ( NH bending), 1516-1489 ( C = C ); 1 H NMR (DMSO-
d 6, 400 MHz, d , ppm ): 4.91 (s, 2 H , CH 2 O ), 6.73 ( d , J = 8.40 Hz, 2 H , aromatic H ), 6.96
( d , J = 8.00 Hz, 2 H , aromatic H ), 7.11 ( t , J = 7.56 Hz, 1 H , aromatic H ), 7.35 ( d , J = 8.80
Hz, 1 H , aromatic H ), 7.40 ( d , J = 7.68 Hz, 1 H , aromatic H ), 7.51 ( d , J = 8.80 Hz, 1 H ,
aromatic H ), 7.58 ( d , J = 8.04 Hz, 1 H , aromatic H ), 8.25 ( d , J = 7.80 Hz, 1 H , aromatic
H ), 8.45 (s, 1 H , aromatic H ), 11.31 (s, 1 H , NH , exchanged with D 2 O ); Analysis
calculated. For C 23 H 14 BrIN 4 O 3; C, 45.09; H, 2.32; Cb , 9.30; Found; C, 46.12; H, 2.43;
H.
4-nitro-2,3-trimethylene-3,4-dihydroquinazolin-4-one white crystals; yield 87%; mp
284–286°C; IR (cm−1): 3336 ( NH ), 3094-3039 ( CH aromatic), 2920 ( CH aliphatic), 1659 (2
C = O ), 1597-1489 ( C = C ); 1 H NMR (DMSO- d 6, 100 MHz, d , ppm ): 1.35-1.49 (m, 6 H ,
piperidine 3 CH 2), 2.45 ( br s , 4 H , piperidine N ( CH 2) 2), 2.87 (s, 2 H , CH 2 N ), 3.17 (s, 1
H , NH replaced by D 2 O ), 4.93 (d, J = 15.64 Hz, 1 H , CH 2 O ), 5.20 (d, J = 15.60 Hz, 1 H ,
CH 2 O ), 6.93 (d, J = 8.92 Hz, 2 H , aromatic H ), 7.29 (d, J = 8.60 Hz, 1 H , aromatic H ), 7.40
(d, J = 8.88 Hz, 2 H , aromatic H ), 7.91 ( d , J = 8.60 Hz, 1 H , aromatic H ), 8.33 (s, 1 H ,
aromatic H ); 13 C NMR (DMSO- δ 6, 100 MHz, d , ppm ) : 24.5 (piperidine CH2 ), 26.0
(piperidine 2CH2 ), 54.8 (piperidine N ( CH2 )2), 63.8 (CH2N), 66.3 ( CH2O ) , 90.3 ( CI ) ,
112.5, 117.50, 124.1, 129.5 132.4, 134.7, 141.4, 146.4, 155.2, 158.1 (aromatic carbons), 158.3
( C = O ), 172.9 ( C = O ); The analysis is calculated for C 22 H 22 BrIN 4 O 3; C, 44.22; N,
3.68; N, 9.38; Found: C, 44.47; N, 3.84; N, 9.47.
To a stirred solution of 3-aminoquinazoline derivative (4) (2.37 g, 5 mmol ) in dry DMF
(5 ml) was added dropwise chloroacetyl chloride (0.65 ml, 5.5 mmol ) and stirring was
continued at room temperature overnight. The solution was poured onto crushed ice with
vigorous stirring, then filtered. The resulting precipitate was washed with water and
recrystallized from ethanolchloroform to give yellow crystals; yield 81%; mp 198–200°C; IR
spectrum (cm−1): 3387 ( NH ), 3194 ( CH aromatic), 2990 ( CH aliphatic), 1725 ( C = O ),
1685 ( C = O ), 1609 ( NH bend), 1489 ( C = C ); 1 H NMR (DMSO- d 6, 400 MHz, d , ppm ):
4.40 (s, 2 H , CH 2 O ), 5.04 ( d , J = 8.40 Hz, 1 H , CH 2 Cl ), 5.11 ( d , J = 8.40 Hz, 1 H , CH
2 Cl ), 6.98 ( d , J = 8.92 Hz, 2 H , aromatic H ); 7.45-7.50 (m, 3 H , aromatic H ); 8.18 ( d , J =
8.60 Hz, 1 H , aromatic H ), 8.43 ( s , 1 H , aromatic H ).
Conclusions
1.
For the first time, the nitration reaction of 2,3-polymethylene-3,4-
dihydroquinazolin-4-ones and quinazolines was studied .
2.
It turned out that this results in the formation of reaction products of electrophilic
substitution of the aromatic ring.
3.
The possibility of the reaction occurring with the substitution of the hydrogen
atom of the aromatic ring in position 6 is shown.
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4.
It was found that it was not possible to introduce a second nitro group into the
quinazoline ring earlier when using an excess of the nitrating mixture (1:4) and under relatively
harsh conditions ( heating to 90-100%).
5.
Nitration of 2,3-polymethylene-3,4-dihydroquinazolines shows that when using a
1:1 reagent ratio, a mono nitro product, 6-nitro derivative, is formed, and at 1:2, a dinitro
product, 6,8-dinitro-2,3-trimethylene-3,4-dihydroquinazoline, is formed.
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F .
A . ,
S u n d b e r g
,
R .
J .
Organic Chemistry:
Reaction Mechanisms and Synthetic Approaches. 5th ed. Springer, 2007.
3. P a r s h a l l , G . W . , N o y o r i , R . Catalysis in Organic Synthesis
4. Wiley-Interscience, 2009.
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