Derivatives of arborine [1-methyl-2-(phenylmethyl)-4(1H)-quinazolinone]

Article abstract of DOI:10.1007/s10593-007-0197-4

A method has been developed for the reaction of 2-cyanomethylbenzoic acid with N-methylanthranilic acid to give 2-[(1-methyl-4-oxo-1,4-dihydro-2- quinazolin-2-yl)methyl]benzoic acid, its esters were synthesized. The spectroscopic chracteristics of the isomeric compounds have been studied and compared in solution and in the solid state.

Full text of DOI:10.1007/s10593-007-0197-4

Chemistry of Heterocyclic Compounds, Vol. 43, No. 10, 2007
DERIVATIVES OF ARBORINE
[1-METHYL-2-(PHENYLMETHYL)-
4(1H)-QUINAZOLINONE]
V. A. Kovtunenko1, T. T. Kucherenko1, R. I. Zubatyuk2,
O. V. Shishkin2, and D. A. Yushchenko1
A method has been developed for the reaction of 2-cyanomethylbenzoic acid with N-methylanthranilic
acid to give 2-[(1-methyl-4-oxo-1,4-dihydro-2-quinazolin-2-yl)methyl]benzoic acid, its esters were
synthesized. The spectroscopic chracteristics of the isomeric compounds have been studied and compared
in solution and in the solid state.
Keywords: 2-methylaminobenzoic acid, 2-cyanomethylbenzoic acid, 2-[(1-methyl-4-oxo-1,3-dihydro-
quinazolin-2-yl)methyl]benzoic acid, X-ray structural analysis.
The alkaloid arborine was separated in 1951 from the plant Glycosmis arborea growing in India and its
structure as 1-methyl-2-(phenylmethyl)-4(1H)-quinazolinone was established in 1961 [1]. The Glycosmis arborea
preparations are used in the ayurvedic system of medicine as antipyretic and anthelmintic agents. Many arborine
derivatives substituted at position 1 show high biological activity [2, 3].
We have previously proposed a method [4] for the synthesis of 2-[(4-oxo-3,4-dihydroquinazolin-
2-yl)methyl]benzoic acid (1a) as a structural analog of the alkaloid glycosminine resulting from the condensation
of 2-cyanomethylbenzoic (2) and anthranilic acids.
Continuing our work in this area we have studied the condensation of acid 2 with N-methylanthranilic
acid (3). The reaction occurs upon heating equimolar amounts of the components in dioxane over 6 h to give 2-(4-
oxo-1-methyl-1,4-dihydro-2-quinazolinylmethyl)benzoic acid (4a) in good yield. The structure of its ester 4c has
been shown using X-ray structural analysis (Figure 1). An interesting feature of this compound is the marked
nonplanarity of the pyrimidine ring and this is likely due to crystal packing effects (shortened intermolecular
contacts C(1)···H(10b') (0.5-x, -0.5+y, z) 2.69 and C(9)···C(15') (0.5-x, 0.5+y, z) 3.39 Å where the sums of the van der
Waal radii are 2.87 and 3.42 Å respectively [5]). The maximal values of the endocyclic torsional angles are C(2)–
C(1)–N(1)–C(8) -6.3(5) and N(1)–C(8)–N(2)–C(7) 6.3(5)º.
Such a disturbance to the heterocycle planarity is evidence of high conformational flexibility in similar
dihydroaromatic rings [6, 7] and this allows the molecule to change its geometry sufficiently easy when steric
strain arises.
The benzene ring C(11)···C(16) is orientated almost perpendicularly to the mean plane of the quinazoline
fragment (torsional angle C(8)–C(10)–C(11)–C(16) -79.2(4)º). The ester substituent lies in the plane of the benzene
__________________________________________________________________________________________
2
Taras Shevchenko National University, Kiev 01033, Ukraine; e-mail: vkovtunenko@univ.kiev.ua. STC
"Institute for Single Crystals", Ukraine National Academy of Sciences, Kharkiv 61001; e-mail:
shishkin@xray.isc.kharkov.com. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1532-1538,
October, 2007. Original article submitted May 31, 2006.
0009-3122/07/4310-1301©2007 Springer Science+Business Media, Inc.
1301

ring (torsional angles C(15)–C(16)–C(17)–O(3) 1.5(4) and C(17)–O(3)–C(18)–C(19) 178.8(3)º). This substituent orientation
is also stabilized by the formation of attractive intramolecular shortened contacts O{2)···H10a) 2.29 and O(3)···H(15)
2.31 Å (sum of van der Waal radii 2.45 Å).
A feature of the IR spectrum of acid 4a is the lowered carbonyl group stretching frequency for the COOH
group at 1685 cm-1, due to the intramolecular hydrogen bond involving the nitrogen atom of the quinazolone ring.
For the same reason an even lower frequency (1670 cm-1) was seen by us in acid 1a. Compound 4a behaves as a
conventional amino acid and shows amphoteric properties, being soluble in 2N HCl and in 2N alkali solution.
The acids 4a and 1a we have obtained can be esterified without difficulty. Both classical (alcohol and a stream of
dry hydrogen chloride) and recent (DMSO + alkyl halide + triethylamine) methods of esterification give a high
yield of the corresponding esters 4b,c and 1b,c.
O
CO2H
CO2H
5
4'
5'
6'
6
7
3'
N
+
NH
Me
1 N
Me
4a–c
8
1'
CN
O
COOR
3
2
–
O
X
N
Me
N
N
+
Me
N
arborine
Me
COOR
O
O
6a,b
Me
NH
N
N
N
COOR
COOR
1a–с
5a,b
5 a R = Me, b R = Et;
1, 4 a R = H, b R = Me, c R = Et;
6 a R = Me, X = MeOSO3, b R = Et, X = ClO4
On the basis of the general understanding of quinazolones we assign a 4(3H)-quinazolinone structure to
the acid 1a. Linked with the method developed for preparing acid 4a and its esters 4b,c it became possible in this
study to determine the position of the quinazolone ring NH proton in acid 1a and its esters 1b,c. For this purpose
we additionally prepared the methyl ester of the acid 1b and both esters 1b,c were alkylated using methyl iodide
in DMSO in the presence of potassium carbonate. The alkylation of quinazolin-4-ones has been quite well studied
and there are reports in the chemical literature of the introduction of an alkyl group not only at atom N(1) [8] and
N(3) [9] but also possible alkylation involving the carbonyl oxygen atom [10].
An important feature in connecting the structure of the methyl esters 1b,c with structures 5a,b is the
presence in the IR spectra of "quinazolone" type absorption bands [11], in addition the esters obtained differ in
melting point and spectroscopic parameters from the esters of 2-[(1-methyl-4-oxo-1,4-dihydro-
2-quinazolinyl)methyl]benzoic acid (4b,c). On the basis of analysing their IR spectra an O-methylated structure
for 5a,b was declined by us and in our hands they proved to be the two pairs of isomeric esters 4b,c and 5a,b. The
melting points of the esters obtained from the 3-methyl-(4H)-quinazol-4-one 5a proved to be lower than the
corresponding 1-methyl-(4H)-quinazol-4-ones 4b,c. At the same time, the chemical shifts of the
proton-containing groups in the NMR spectra of the isomeric esters proved very similar. The greatest difference
1302

occurred in the resonance for the N-methyl group protons of compounds 4b,c and 5a,b. The signals for this group
assigned to the 3-methyl-(4H)-quinazol-4-one series were to higher field by 0.2 ppm. In the IR spectra of the
isomeric esters 4b,c and 5a,b the stretching vibrations assigned to the ester carbonyl group were seen at the same
frequency of 1695 cm-1 which points to the disappearance of the intramolecular hydrogen bond in the methylated
products. For all four compounds 4b,c and 5a,b the ester C–O stretching vibrations appear as strong, single bands
in the range 1070-1080 cm-1. As regards the carbonyl group absorption of the quinazolone ring there clearly arises
a difference among the isomeric esters. In esters 4b,c the carbonyl group absorbs at 1630 cm-1 and in the esters
5a,b at 1655-1660 cm-1. It should be noted that such a remarkably low frequency for νC=O, particularly for esters
4b,c, is in agreement with tabulated νC=O frequencies for other isomeric quinazol-4-ones [12].
Fig. 1. Molecular structure of ethyl 2-[(1-methyl-4-oxo-1,4-dihydro-2-quinazolinyl)methyl]benzoate (4c).
Thermal ellipsoids for the non-hydrogen atoms are shown at the 30% probability level.
The electronic transitions for the esters 4c and 5b are observed in three regions: 1) at lowest wavelength
(less than 250 nm) single bands with a uniform structure and close intensities; 2) in the medium region
(260-285 nm) two local maxima, in ester 5b being close in intensity and in compound 4c the long wavelength
being more intense; 3) at longer wavelength (295-320 nm) two localized maxima in each of the spectra but in
both compounds the first being more intense than the second.
The differences in the electronic spectra of esters 4c and 5b consist of differences in the absorption band
intensities in the medium and long wavelength regions. In compound 5 the intensity of the medium band is
greater (∆ε ~ 2000) and the long wavelength band lower (∆ε ~ 4000) than the intensities of the corresponding
bands in ester 4c. Comparison of the electronic spectra of the ester 1c with the spectra of the model compounds 4c
and 5b shows a similarity in the features of the spectra of esters 5b and 1c and a difference of the latter from the
electronic spectrum of ester 4c. This leads us to conclude that the ester 1c has a 4(3H)-quinazolinone structure.
Although less thorough, the same conclusion can be reached by comparison of the IR spectra of the esters 4c, 5b
and 1c.
The esters 4a-c and 5a,b show marked basic properties. They readily form simple salts with mineral acids
and are quaternized by alkylating agents. Moreover, the different starting esters (e.g. the pairs 4b and 5a or 4c and
5b) give identical quaternary salts (e.g. 6a and 6b respectively). In these salts the N(1)-methyl group proton
resonances are seen at higher field than the N(3)-methyl protons (∆δ ~ 0.3-0.4 ppm). The assignment of signals
was made in this case on the basis of NOE experiments.
1303

EXPERIMENTAL
IR spectra for the compounds in CsI tablets were recorded on a Pye-Unicam SP3-300 instrument.
1H NMR spectra were measured on a Varian Mercury 400 (400 MHz) spectrometer using DMSO-d6 solvent and
TMS as internal standard. UV spectra were recorded on a Specord M-40 spectrophotometer in methanol solvent
at 5×10-5 M concentration.
X-ray Structural Analysis. Crystals of 4c are rhombic (ethanol), C19H18N2O3, at 298 K: a = 15.694(1),
b = 10.6785(6), c = 19.539(1) Å, V = 3274.5(4) Å3, Mr = 322.35, Z = 8, space group Pbca, dcalc = 1.308 g/cm3,
µ(MoKα) = 0.09 mm-1, F(000) = 1360. The unit cell parameters and intensities of 9448 reflections (3024
independent with Rint = 0.053) were measured on an Xcalibur 3 automatic, four circle diffractometer (MoKα,
graphite monochromator, CCD detector, ω-scanning, 2θmax = 51º). The structure was solved by a direct method
using the SHELXTL program package [13]. The positions of the atoms were calculated geometrically and refined
using the "riding" model with Uiso(H) = nUeq (C) (n = 1.5 for methyl groups and n = 1.2 for other hydrogen
atoms). The structure was refined in F2 full matrix least squares analysis for non-hydrogen atoms to wR2 = 0.182
for 3024 reflections (R1 = 0.074 for 1721 reflections with F > 4σ(F), S = 1.13). The crystallographic data
(excluding the structural factors) has been placed in the Cambridge structural data base (reference CCDC
608867).
2-Cyanomethylbenzoic Acid (2) was prepared according to method [14].
2-[(4-Oxo-3,4-dihydro-2-quinazolinyl)methyl]benzoic acid (1a) was prepared according to method [4].
1H NMR spectrum, δ, ppm (J, Hz): 12.7 (1H, s, COOH); 12.1 (1Н, s, NH); 8.05 (1H, d, J = 8.0, H-5); 7.91 (1H, d,
J = 7.2, H-6'); 7.65 (1H, t, J = 7.6, H-7); 7.47 (1H, t, J = 7.8, H-4'); 7.42 (1H, d, J = 8.4, H-8); 7.37 (1H, t, J = 8.0,
H-6); 7.36 (1H, t, J = 8.0, H-5'); 7.32 (1H, d, J = 8.0, H-3'); 4.35 (2H, s, 1'-CH2).
Methyl 2-[(4-Oxo-3,4-dihydro-2-quinazolinyl)methyl]benzoate (1b). A. Triethylamine (0.3 ml,
2 mmol) and methyl iodide (0.13 ml, 2 mmol) were added dropwise to a solution of acid 1a (0.56 g, 2 mmol) in
DMSO (5 ml). The reaction mixture was stirred and held at room temperature for 48 h and then diluted with
water. The colorless precipitate was washed with water and alcohol. Yield 0.56 g (90%); mp 188ºC (acetic acid).
B. A suspension of acid 1a (1.12 g, 4 mmol) in dry methanol (50 ml) was saturated with dry hydrogen
chloride for 30 min until the precipitate dissolved. The reaction mixture was refluxed for 3 h, solvent removed
under reduced pressure, and the residue was treated with saturated sodium bicarbonate solution. The precipitate
was filtered off and washed with water and alcohol. Yield 1 g (81%).
The substance obtained by method A was spectroscopically identical to the compound prepared by
method B and the melting point of a mixed sample was not depressed. IR spectrum, ν, cm-1: 3190 (N–H), 1710
(ester C=O), 1670 (quinazolone C=O), 1610 (C=N), 1480, 1450, 1430, 1270. 1H NMR spectrum, δ, ppm (J, Hz):
12.2 (1Н, s, NH); 8.05 (1H, d, J = 7.6, H-5); 7.89 (1H, d, J = 8, H-6'); 7.65 (1H, t, J = 7.8, H-7); 7.50 (1H, t,
J = 7.8, H-4'); 7.39 (1H, t, J = 8.0, H-5'); 7.39 (1H, t, J = 8.0, H-6); 7.36 (1H, d, J = 7.2, H-3'); 7.36 (1H, d,
J = 7.2, H-8); 4.31 (2H, s, 1'-CH2); 3.77 (3H, s, –OCH3). Found, %: C 70.23; H 4.69; N 9.33. С17H14N2O3.
Calculated, %: C 70.38; H 4.79; N 9.52.
Ethyl 2-[(4-Oxo-3,4-dihydro-2-quinazolinyl)methyl]benzoate (1c) with mp 176ºC (acetic acid) was
prepared by the method in [4]. IR spectrum, ν, cm-1: 3200 (N–H), 1710 (ester C=O), 1670 (quinazolone C=O),
1
1600 (C=N), 1250. UV spectrum, λmax, nm (log ε): 313 (3.59), 301 (3.67), 269 (3.92), 263 (3.94). H NMR
spectrum, δ, ppm (J, Hz): 12.22 (1Н, s, NH); 8.07 (1H, d, J = 8.0, H-5); 7.88 (1H, d, J = 6.8, H-6'); 7.70 (1H,
t, J = 6.8, H-7); 7.44 (1H, t, J = 6.8, H-4'); 7.44 (1H, t, J = 6.8, H-5'); 7.44 (1H, t, J = 6.8, H-6); 7.39 (1H, d,
J = 8.4, H-3'); 7.39 (1H, d, J = 8.4, H-8); 4.31 (2H, s, 1'-CH2); 4.19 (2H, q, J = 7.2, OCH2); 1.24 (3H, t, J = 7.2,
OCH2CH3).
2-(1-Methyl-4-oxo-1,4-dihydro-2-quinazolinylmethyl)benzoic Acid (4a). A mixture of 2-cyanomethyl-
benzoic acid (2, 0.81 g, 5 mmol) and N-methylanthranilic acid (3, 0.76 g, 5 mmol) was dissolved in dry dioxane
(30 ml) and the mixture was refluxed for 6 h. The precipitate was filtered, washed with 2-propanol, and
1304

recrystallized from DMF to give the colorless compound. Yield 1.25 g (88%); mp 259ºC (DMF). IR spectrum,
ν, cm-1: 2660-2960 (N–H), 1690 (carboxyl C=O), 1680 (4-quinazolone C=O), 1580 (C=N), 1530 (C–N), 1450,
1
1430, 1250 (C–O). H NMR spectrum, δ, ppm (J, Hz): 12.7 (1Н, s, CO2H); 8.04 (1H, d, Jо = 7.6, Jm = 2.0, H-5);
7.99 (1H, d, J = 7.6, H-6'); 7.75 (1H, t, Jо = 7.6, Jm = 1.2, H-7); 7.66 (1H, d, J = 8.8, H-8); 7.49 (1H, t, J = 7.2,
H-4'); 7.42 (1H, t, J = 7.6, H-6); 7.37 (1H, t, J = 7.4, H-5'); 7.27 (1H, d, J = 6.8, H-3'); 4.60 (2H, s, 1'-CH2); 3.79
(3H, s, –NCH3). Found, %: C 68.98; H 4.83; N 9.64. С17H14N2O3. Calculated, %: C 69.38; H 4.79; N 9.52.
Methyl 2-[(1-Methyl-4-oxo-1,4-dihydro-2-quinazolinyl)methyl]benzoate (4b) was prepared from acid
4a using the preparative method B for compound 1b. Yield 80%; mp 202ºC (2-propanol). IR spectrum, ν, cm-1:
1
1710 (ester C=O), 1630 (quinazolone C=O), 1580 (C=N), 1530, 1470, 1450, 1290, 1250. H NMR spectrum, δ,
ppm (J, Hz): 8.03 (1H, d, J = 8.0, H-5); 7.99 (1H, d, J = 8.0, H-6'); 7.78 (1H, t, J = 7.6, H-7); 7.71 (1H, d, J = 8.0,
H-8); 7.56 (1H, t, J = 7.4, H-4'); 7.44 (1H, t, J = 8.0, H-6); 7,42 (1H, t, J = 8.0, H-5'); 7.33 (1H, d, J = 7.6, H-3');
4.59 (2H, s, 1'-CH2); 3.81 (3H, s, NCH3); 3.72 (3H, s, OCH3). Found, %: C 70.26; H 5.30; N 9.17. С18H16N2O3.
Calculated, %: C 70.12; H 5.23; N 9.09.
Ethyl 2-[(1-Methyl-4-oxo-1,4-dihydro-2-quinazolinyl)methyl]benzoate (4c) was prepared similarly to
compound 4b by esterification of acid 4a using absolute ethanol. Yield 85%; mp 200ºC (2-propanol). IR
spectrum, ν, cm-1: 1700 (ester C=O), 1630 (quinazolone C=O), 1580 (C=N), 1530,1470, 1450, 1290, 1250. UV
spectrum, λmax, nm (log ε): 317 (3.84), 305 (3.97), 275 (3.85), 266 (3.80). 1H NMR spectrum, δ, ppm (J, Hz): 8.03
(1H, d, J = 7.6, H-5); 7.98 (1H, d, J = 7.2, H-6'); 7.77 (1H, t, J = 7.6, H-4'); 7.71 (1H, d, J = 8.4, H-3'); 7.54 (1H,
t, J = 7.8, H-7); 7,43 (1H, t, J = 7.6, H-6); 7.40 (1H, t, J = 7.6, H-5'); 7.32 (1H, d, J = 8.0, H-8); 4.59 (2H, s,
1'-CH2); 4.15 (2H, q, J = 7.2, OCH2); 3.81 (3H, s, NCH3); 1.2 (3H, t, J = 7.2, OCH2CH3). Found, %: C 71.06;
H 5.70; N 8.81. С19H18N2O3. Calculated, %: C 70.79; H 5.63; N 8.69.
Methyl 2-[3-Methyl-4-oxo-3,4-dihydro-2-quinazolinyl)methyl]benzoate (5a). Potassium carbonate
(0.6 g) was added to a solution of the ester 1b (0.56 g, 2 mmol) in DMSO (5 ml). Methyl iodide (0.25 ml,
4 mmol) was then introduced dropwise with stirring and the reaction mixture was held for 48 h at room
temperature. It was diluted with water and the colorless precipitate was filtered off and washed with water and
alcohol. Yield 0.5 g (85%); mp 155ºC (acetic acid). IR spectrum, ν, cm-1: 1700 (ester C=O), 1670 (quinazolone
C=O), 1580 (C=N), 1480, 1460, 1430, 1250. 1H NMR spectrum, δ, ppm (J, Hz): 8.10 (1H, d, J = 7.6, H-5); 7.96
(1H, d, J = 7.6, H-5'); 7.66 (1H, t, J = 7.6, H-7); 7.53 (1H, t, J = 7.6, H-4'); 7.41 (1H, t, J = 7.6, H-6); 7.41 (1H, t,
J = 7.6, H-5'); 7.34 (1H, d, J = 8.4, H-8); 7.31 (1H, d, J = 7.6, H-3'); 4.60 (2H, s, 1'-CH2); 3.72 (2H, s, –OCH3);
3.62 (3H, s, 3-CH3). Found, %: C 70.21; H 5.28; N 9.14. С18H16N2O3. Calculated, %: C 70.12; H 5.23; N 9.09
Ethyl 2-[(3-Methyl-4-oxo-3,4-dihydro-2-quinazolinyl)methyl]benzoate (5b) was prepared from ester
1c, potassium carbonate, and methyl iodide in DMSO by the method reported for ester 5a. Yield 87%; mp 121ºC
(acetic acid). IR spectrum, ν, cm-1: 1700 (ester C=O), 1670 (quinazolone C=O), 1580 (C=N), 1470, 1250.
UV spectrum, λmax, nm (log ε): 313 (3.59), 305 (3.68), 273 (3.96), 263 (3.96). 1H NMR spectrum, δ, ppm (J, Hz):
8.09 (1H, d, J = 7.6, H-5); 7.95 (1H, d, J = 8.0, H-6'); 7.64 (1H, t, J = 7.6, H-7); 7.52 (1H, t, J = 7.2, H-4'); 7.39
(1H, t, J = 7.6, H-6); 7.39 (1H, t, J = 7.6, H-5'); 7.33 (1H, d, J = 8.4, H-3'); 7.30 (1H, d, J = 6.8, H-8); 4.57 (2H, s,
1'-CH2); 3.60 (3H, s, 3-CH3); 4.14 (2H, q, J = 7.2, OCH2CH3); 1.16 (3H, t, J = 7.2, OCH2CH3). Found, %:
C 70.96; H 5.55; N 8.78. С19H18N2O3. Calculated, %: C 70.79; H 5.63; N 8.69.
2-[2-(Ethoxycarbonyl)phenyl]methyl-1,3-dimethyl-4-oxo-1,4-dihydroquinazolin-3-ium Methylmetho-
sulfate (6a). A. A mixture of compound 5a (0.62 g, 2 mmol) and dimethylsulfate (0.4 ml, 2.2 mmol) was fused on
an oil bath at 120-140ºC for 1 h. The solid residue was triturated with acetone and filtered. Yield 0.53 g (61%);
mp 158ºC (alcohol).
B. Prepared from the methyl ester 4b and dimethylsulfate by the method given for 6a.
The substance obtained by method A was spectroscopically identical to that prepared by method B and
the melting point of a mixed sample was not depressed. IR spectrum, ν, cm-1: 1710 (ester C=O), 1615
1
(quinazolone C=O), 1555 (C=N), 1490, 1270, 1250, 1225. H NMR spectrum, δ, ppm (J, Hz): 8.43 (1H, d,
1305

J = 7.6, H-5); 8.20-8.12 (3H, m, H-7,4',6'); 7.87 (1H, t, J = 7.6, H-6); 7.58-7.51 (2H, m, H-3',5'); 7.39 (1H, d,
J = 8.0, H-8); 5.28 (2H, s, 1'-CH2); 4.05 (3H, s, 3-CH3); 3.70 (3H, s, 1-CH3); 3.94 (3H, s, –COOCH3); 3.45 (3H, s,
–COCH3). Found, %: C 55.18; H 5.19; N 6.57; S 7.51. С20H22N2O7S. Calculated, %: C 55.29; H 5.10; N 6.45; S
7.38.
2-[2-(Ethoxycarbonyl)phenyl]methyl-1,3-dimethyl-4-oxo-1,4-dihydroquinazolin-3-ium Perchlorate
(6b). A. A mixture of compound 4c (0.65 g, 2 mmol) and methyl tosylate (0.4 g, 2.1 mmol) was fused on an oil
bath at 140ºC for 1 h. The melt was cooled, dissolved in ethanol (10 ml), and treated with a saturated alcohol
solution of NaClO4. The colorless precipitate was filtered off and washed with water. Yield 0.54 g (62%);
mp 158ºC (alcohol).
B. Prepared from the ethyl ester 5b and methyl tosylate using method A in the synthesis of compound 6b.
The substance obtained by method A was spectroscopically identical to that obtained by method B and
the melting point of a mixed sample was not depressed. IR spectrum, ν, cm-1: 1720 (ester C=O), 1615
(quinazolone C=O), 1555 (C=N), 1490, 1270, 1250. UV spectrum, λmax, nm (log ε): 347 (3.52), 290 (3.51), 284
1
(3.56). H NMR spectrum, δ, ppm (J, Hz): 8.39 (1H, d, J = 7.6, H-5); 8.18–8.11 (3H, м, H-7,4',6'); 7.87 (1H, t,
J = 7.0, H-6); 7.56-7.50 (2H, m, H-3',5'); 7.40 (1H, d, J = 8.0, H-8); 5.22 (2H, s, 1'-CH2); 4.07 (3H, s, 3-CH3);
3.65 (3H, s, 1-CH3); 4.39 (2H, q, J = 7.2, –OCH2CH3); 1.42 (3H, t, J = 7.2, –OCH2CH3). Found, %: C 55.23;
H 4.96; Cl 8.22; N 6.53. С20H21ClN2O7. Calculated, %: C 54.99; H 4.85; Cl 8.12; N 6.41.
The authors thank Dr. A. V. Turov for the NOE experiments and for accumulating the COSY
NMR spectra.
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