Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones and Their Reactions with Alkyl Halides and α-Glycopyranosyl Bromides

Article abstract of DOI:10.1002/jhet.3623

A series of 3-substituted 2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones 4a–e were synthesized from the reaction of 3-aminonaphthalene-2-carboxylic acid 1 with isothiocyanate derivatives 2a–e. The alkylation of 4a–e with alkyl halides gave 3-substituted 2-alkylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin-4-ones 5a–o. S-Glycosylation was carried out via the reaction of 4a–e with glycopyranosyl bromides 7a and 7b under anhydrous alkaline conditions. The structure of the compounds was established as S-nucleoside and not N-nucleoside. Conformational analysis has been studied by homonuclear and heteronuclear two-dimensional NMR methods (2D DFQ-COSY, heteronuclear multiple quantum coherence, and heteronuclear multiple bond correlation). The S site of alkylation and glycosylation was determined from the ¹H and?¹³C heteronuclear multiple quantum coherence experiments.

Full text of DOI:10.1002/jhet.3623

Month 2019
Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-
dihydro-1H-benzo[g]quinazolin-4-ones and Their Reactions with Alkyl
Halides and α-Glycopyranosyl Bromides
a
Ahmed I. Khodair,
Mona A. Elsafi,b and Siham A. Al-Issac
*
aChemistry Department, Faculty of Science, Kafrelsheikh University, Kafrelsheikh 33516, Egypt
bChemistry Department, College of Science, Taibah University, Al-Madinah Al-Monawarah 1343, Saudi Arabia
cChemistry Department, College of Science, Princess Nourah Bint Abdulrahman University, Riyadh 48828-1161,
Saudi Arabia
*E-mail: khodair2020@yahoo.com
Received November 14, 2018
DOI 10.1002/jhet.3623
Published online 00 Month 2019 in Wiley Online Library (wileyonlinelibrary.com).
A series of 3-substituted 2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones 4a–e were synthesized
from the reaction of 3-aminonaphthalene-2-carboxylic acid 1 with isothiocyanate derivatives 2a–e. The al-
kylation of 4a–e with alkyl halides gave 3-substituted 2-alkylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin-
4-ones 5a–o. S-Glycosylation was carried out via the reaction of 4a–e with glycopyranosyl bromides 7a
and 7b under anhydrous alkaline conditions. The structure of the compounds was established as S-
nucleoside and not N-nucleoside. Conformational analysis has been studied by homonuclear and
heteronuclear two-dimensional NMR methods (2D DFQ-COSY, heteronuclear multiple quantum coherence,
and heteronuclear multiple bond correlation). The S site of alkylation and glycosylation was determined from
1
the H and 13C heteronuclear multiple quantum coherence experiments.
J. Heterocyclic Chem., 00, 00 (2019).
INTRODUCTION
which can interact with different cell biosynthesis. During
the last decades, an intensive research was dedicated to the
discovery of more effective, selective, and nontoxic new
nucleoside derivatives [27–29]. We have reported that S-
glycosylated hydantoin derivatives showed potent activity
against the herpes simplex virus [30], the human
immunodeficiency virus [31], and the leukemia subpanel
[32]. In continuation of our work on the synthesis of novel
nucleosides as potential antiviral and antitumor agents and
keeping in mind the biological significance of 2-
thioxoquinazolin-4-ones [33–39], we hereby report the
synthesis and spectroscopy of a new series of S-alkylated
and S-glycosylated 3-substituted 2-thioxo-2,3-dihydro-1H-
benzo[g]quinazolin-4-one bases (Schemes 1 and 2). This
is the first time to prepare S-glycosides of 3-substituted
2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones via
new synthetic strategies. Abdel-Megeed et al. [40] and El-
Barbary et al. [41] previously prepared the acetylated S-
Quinazolines are considered to be important chemical
synthons of various compounds of physiological
significance and pharmaceutical utility. They possess a
variety of biological effects including antihypertensive
[1,2], antimicrobial [3,4], antihyperlipidemic [5,6], anti-
inflammatory [7,8], and anticonvulsant [9–13] activities.
Many quinazolines contributed to the quest for an ultimate
antitumor chemotherapeutic agent [14–21]. It was reported
that 2-thioxo-3-substituted quinazolinones [22] and their
S-methyl thioether counterparts, as well as the 6-
substituted quinazolinone derivatives [23], showed
potential antitumor potency. 7-(4-Chlorophenyl)-5-
phenyl-2-(β-D-glucopyranosylthio)pyrido[2,3-d]pyrimidin
-4-one showed promising anti-inflammatory and analgesic
activities [24]. Moreover, nucleoside analogs constitute an
important class of therapeutic agents in the treatment of
cancers and viral infections [25,26]. The mode of action of
these derivatives is based upon their intracellular
conversion to their phosphorylated forms (nucleotides),
glycosylated
3-substituted
2-thioxoquinazolin-4-one
derivatives as nucleobases but failed to convert them into
the corresponding deacylated S-glycosides.
© 2019 Wiley Periodicals, Inc.

A. I. Khodair, M. A. Elsafi, and S. A. Al-Issa
Vol 000
Scheme 1. Synthesis of compounds 3a–e, 4a–e, and 5a–o.
RESULTS AND DISCUSSION
IR absorption spectra of 5a-o signals were characterized
by the absence of signals for NH and C=S groups. The
1H-NMR spectra of compounds 4a–e obtained in
DMSO-d6 at 500 MHz showed a triplet at δH 7.51–
7.53 ppm with coupling constant (J) values 7.2 Hz
assigned to H-8, a triplet at δH 7.62 ppm (J = 7.25–
7.50 Hz) assigned to H-7, a singlet at δH 7.75–7.84 ppm
assigned to H-10, a doublet at 7.92–7.95 ppm (J = 8.25–
8.50 Hz) assigned to H-9, a doublet at δH 8.12–8.24 ppm
(J = 8.25–8.50 Hz) assigned to H-6, a singlet at δH 8.62–
8.71 ppm assigned to H-5, and a singlet at δH 12.88–
13.00 ppm assigned to NH.
The spectral data compare favorably with the literature
data for the 3-(4-methoxyphenyl)-2-thioxo-2,3-dihydro
quinazolin-4(1H)-one recorded at 300 and 75 MHz in
DMSO-d6 [42]. The 13C-NMR spectra of compounds 4a–
e recorded at 125 MHz in DMSO-d6 revealed the
presence of carbon signals in the region 158.7–
160.0 ppm and 175.4–179.0 ppm corresponding to the
carbonyl (C-4) and thiocarbonyl (C-2) groups, respec
tively. Furthermore, data from the elemental analyses
have been found to be in conformity with the assigned
structure. Also, the molecular ion recorded in the mass
spectrum is also in agreement with the molecular weight
of the compound. 1H-NMR (500 MHz, DMSO-d6)
spectrum of compound 5k showed a singlet at 3.40 ppm
The key intermediates for the synthesis of acyclic
thioglycosides are shown in Scheme 1. 3-Substituted 2-
thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones (4a–e)
were synthesized by one-pot-reaction of 3-aminon
aphthalene-2-carboxylic acid (1) and the appropriate
alkyl/aryl isothiocyanates 2a–e in refluxing absolute
ethanol in the presence of triethylamine as base catalyst.
The reaction proceeds through the formation of 3-(3-
substituted thiourea)-naphthalene-2-carboxylic acids (3a-
e) as intermediates to afford compounds 4a–e. Com
pounds 4a–e were then reacted with the appropriate alkyl
halides, namely, ethyl bromide, ethyl bromoacetate, or 1-
chloro-2-methoxyethane, to yield the corresponding 3-
substituted
2-methylsulfanyl-2,3-dihydro-1H-benzo[g]
quinazolin-4-ones (5a–e), 3-substituted 4-oxo-3,4-dihydro
quinazolin-2-ylsulfanyl-acetic acid ethyl esters (5f–j), and
3-substituted 2-ethoxymethylsulfanyl-2,3-dihydro-1H-ben
zo[g]quinazolin-4-ones (5k–o), respec-tively (Scheme 1).
The structures of 4a–e and 5a–o were established and
confirmed by the combination of spectroscopic data
(NMR, IR, and mass spectrometric techniques) and ele
mental analyses. The IR absorption spectra of 4a–e were
characterized in the presence of signal for NH group at
vmax 3140–3257 cmꢀ1 and the presence of signal for the
thiocarbonyl group at vmax 1255–1279 cmꢀ1. While the
assigned to N3-CH3,
a triplet at δH 3.59 ppm
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-
benzo[g]quinazolin-4-ones and Their Reactions with Alkyl Halides and α-
Glycopyranosyl Bromides
Scheme 2. Synthesis of compounds 6a–e, 8a–h, and 9a,b.
(J = 6.25 Hz) assigned to SCH2, a singlet at 3.67 ppm
assigned to OCH3, a triplet at 3.81 ppm (J = 6.25 Hz)
assigned to the OCH2, a triplet at δH 7.50 ppm
(J = 7.25 Hz) assigned to 8-H, a triplet at δH 7.59 ppm
(J = 7.25 Hz) assigned to 7-H, a doublet at 7.94 ppm
(J = 8.50 Hz) assigned to 9-H, a singlet at δH 7.98 ppm
assigned to 10-H, a doublet at δH 8.03 ppm (J = 8.50 Hz)
assigned to 6-H, and a singlet at δH 8.80 ppm assigned to
5-H. The 13C-NMR (500 MHz, DMSO-d6) spectrum of
5k showed a singlet at δC 155.50 and 162.20 ppm
assigned to –N¼C–S– at C-2 and the carbonyl group at
C-4, respectively, indicated that the site of the alkylation
is the sulfur atom rather than the nitrogen atom. These
data are also in agreement with the 13C-NMR (300 MHz,
DMSO-d6) spectrum of 3-ethyl-2-[2-(4-methoxyphenyl)-
afford the S-glycosylated nucleosides 8a–h in good yields
(58–96%) (Scheme 2). Thin-layer chromatography (TLC)
(using 98:2 CH2Cl2/MeOH (v/v) as eluent) indicated the
formation of the pure compounds. The structures of the
S-glycoside 8a–h were confirmed by elemental analysis
and spectral data (IR, H-NMR, and 13C-NMR). The H-
NMR (500 MHz, CDCl3) spectra of compounds 8a–h
showed the anomeric proton of the glucose moiety as a
doublet at δH 5.85–6.08 ppm with a coupling constant
2J1′,2′ = 10.50–11.00 Hz indicating β-configuration of the
anomeric center. The other protons of the glucopyranose
ring resonated at δH 4.09–5.48 ppm, while the four
acetoxy groups appeared as four singlets at δH 1.88–
2.20 ppm. The 13C-NMR (500 MHz, CDCl3) of
compounds 5k–o and 8a–h revealed the absence of the
thione carbon atom at about 175.43–179.00 ppm, and a
resonance of –N¼C–N– carbon atom (C-2) of
compounds 5k–o and 8a–h at δC 154.40–157.20 and
151.70–153.53 ppm, respectively, indicated the chemical
shift of the corresponding carbon atom (C-2) (Fig. 1).
The signals at δ = 169.63, 170.30, and 170.70 ppm were
due to the four acetoxy carbonyl atoms (4C¼O), and the
six signals at δ 62.04, 68.33, 68.80, 74.14, 76.53, and
82.37 ppm were assigned to C-6′, C-2′, C-3′, C-4′, C-5′,
and C-1′, respectively. Moreover, the IR spectra of
1
1
2-oxo-ethylthio]quinazolin-4(3H)-one [35], because
–
N¼C–S– at C-2 appears at δc 153.40 ppm and the
carbonyl group at C-4 appears at δC 160.60 ppm.
The key intermediates for the synthesis of cyclic
thioglycosides are shown in Scheme 2. Treatment of 4a–f
with 1.1 equivalents of NaH in anhydrous acetonitrile
furnished the sodium salts of 2-thioxo-4-thiazolidinones
(6a–e), which in turn were treated with 2,3,4,6-tetra-O-
acetyl-α-D-glucopyranosyl bromide (7a) and/or 2,3,4,6-
tetra-O-acetyl-α-D-galactopyranosyl bromide (7b) to
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. I. Khodair, M. A. Elsafi, and S. A. Al-Issa
Vol 000
Figure 1. The chemical shift of the corresponding carbon atom at position 2 in 4a–e, 5a–o, and 8a–h. [Color figure can be viewed at wileyonlinelibrary.
com]
compounds 8a–h revealed the absence of the stretching
signal of a thione group. These data are also in agreement
with the 13C-NMR (DMSO-d6) spectrum of 7-(4-
chlorophenyl)-5-phenyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-
glucopyranosylthio)pyrido[2,3-d]pyrimidine-4-one [37],
because the carbonyl at C-4 appears at δc 163.20 ppm
and –N¼C–N– carbon atom (C-2) appears at δC
152.20.8 ppm, indicating the presence of S-glycosylation.
Removal of the acetyl groups from the glycon moiety of
8b and 8d with saturated 5% NH3/MeOH solution at
room temperature furnished the corresponding free
nucleosides 9a and 9b, respectively (Scheme 2). The
structures of 9a and 9b were confirmed on the basis of
their spectroscopic and mass spectral data. The mass
spectrum of 9b showed a molecular ion peak at m/
carboxylic acid (1) (1.87 g, 10 mmol) and triethylamine
(2.00 mL, 22.22 mmol) in absolute ethanol (50 mL) was
added the appropriate alkyl/aryl isothiocyanates 2a–e
(11 mmol). The mixture was refluxed until the starting
material was consumed (4 h; TLC, ethyl acetate/
methanol, 99.9:0.1) and cooled at room temperature. The
reaction mixture was diluted with water and neutralized
with diluted hydrochloric acid. The solid separated was
collected by filtration and recrystallized from ethanol to
give the products 4a–e in quantitative yields.
3-Methyl-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one
(4a). Yield: 2.13 g (88%), mp: 308–310°C. MS: m/z: 242
(M+, 80%). Calculated for C13H10N2OS (242.30): C,
64.44; H, 4.16; N, 11.56. Found: C, 64.22; H, 4.27; N,
11.38. IR (KBr): ν 3232 (NH), 1654 (C¼O), 1279 (C¼S)
1
cmꢀ1. H-NMR (500 MHz, DMSO-d6): δ = 3.71 (3H, s,
1
z = 466, while the H-NMR spectrum showed a doublet
2
CH3), 7.51 (1H, t, J = 7.25 Hz, H-8), 7.64 (1H, d,
J = 7.25 Hz, H-7), 7.76 (1H, s, H-10), 7.94 (1H, d,
J = 8.50 Hz, H-9), 8.14 (1H, d, J = 8.50 Hz, H-6), 8.71
(1H, s, 5-H H-5), 13.00 (1H, s, NH). 13C-NMR
(500 MHz, DMSO-d6): δ = 33.70 (CH3), 111.57 (C-4a),
116.00 (C-9), 126.04 (C-7), 127.70 (C-6, C-8), 129.74
(C-10), 130.01 (C-5, C-9a), 135.90 (C-5a), 136.00 (C-
at δH 5.70 with J1′,2′ = 9.8 Hz, corresponding to the 1′-
H and indicating a β-configuration. C-2 of 9b resonated
at δC 154.83 ppm, establishing the S-glycosylation.
Furthermore, in the heteronuclear spectra (heteronuclear
multiple quantum coherence and DFQ-COSY) of 9a,b,
no such correlation was shown between C-10a and 1′-H,
which is an indication of the S-glycosylation. The
nucleoside bases 4 can be utilized as starting materials
for the synthesis of other carbohydrate derivatives as
deoxy, amino, and azido nucleosides.
10a), 160.00 (C-4), 179.00 (C-2).
3-Ethyl-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one
(4b). Yield: 1.41 g (55%), mp: 288–290°C. MS: m/z: 256
(M+, 3%). Calculated for C14H12N2OS (256.32): C, 65.60;
H, 4.72; N, 10.93. Found: C, 65.46; H, 4.84; N, 10.70. IR
(KBr): ν 3257 (NH), 1653 (C¼O), 1261 (C¼S) cmꢀ1. 1H-
NMR (500 MHz, DMSO-d6): δ = 1.27 (3H, t, J = 7.00 Hz,
CH3), 4.50 (2H, q, J = 7.00 Hz, CH2), 7.52 (1H, t,
J = 7.50 Hz, H-8), 7.64 (1H, t, J = 7.50 Hz, H-7), 7.77
(1H, s, H-10), 7.95 (1H, d, J = 8.50 Hz, H-9), 8.15 (1H,
d, J = 8.50 Hz, H-6), 8.71 (1H, s, H-5), 12.90 (1H, s,
NH). 13C-NMR (500 MHz, DMSO-d6): δ = 12.71 (CH3),
41.44 (CH2), 111.62 (C-4a), 116.09 (C-9), 126.11 (C-7),
127.73 (C-8), 129.75 (C-6), 129.95 (C-10), 130.03 (C-5,
C-9a), 135.42 (C-5a), 136.62 (C-10a), 160.00 (C-4),
EXPERIMENTAL
General procedures. All melting points were taken on
Electrothermal IA 9100 series digital melting point
apparatus. Microanalytical data (in accord with the
calculated values) were performed by Vario, Elementar
apparatus (Shimadzu). The IR spectra (KBr) were
recorded on a Perkin–Elmer 1650 spectrometer (USA).
1H-NMR and 13C-NMR spectra were determined on a
JEOL ECA-500. Chemical shifts were expressed in ppm
relative to SiMe4 as internal standards and DMSO-d6 or
CDCl3 or CD3OD as solvent. Mass spectra were recorded
on 70 eV EI Ms-QP 1000 EX (Shimadzu).
175.43 (C-2).
3-Allyl-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one
(4c). Yield: 1.88 g (70%), mp: 258–260°C. MS: m/z:
268 (M+, 6%). Calculated for C15H12N2OS (268.07): C,
65.14; H, 4.51; N, 10.44. Found: C, 65.42; H, 4.68; N,
10.30. IR (KBr): ν 3166 (NH), 1653 (C¼O), 1255
3-Substituted 2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-
4-ones (4a–e).
To a mixture of 3-aminonaphthalene-2-
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-
benzo[g]quinazolin-4-ones and Their Reactions with Alkyl Halides and α-
Glycopyranosyl Bromides
(C¼S) cmꢀ1. H-NMR (500 MHz, DMSO-d6): δ = 5.14
(2H, d, J = 4.86 Hz, H-1allyl), 5.24 (1H, m, H-3allyl),
5.97 (1H, m, H-2allyl), 7.51 (1H, t, J = 7.35 Hz, H-8),
7.64 (1H, t, J = 7.35 Hz, H-7), 7.75 (1H, s, H-10),
7.95 (1H, d, J = 8.25 Hz, H-9), 8.00 (1H, d,
J = 8.25 Hz, H-6), 8.62 (1H, s, H-5), 12.88 (1H, s,
NH). 13C-NMR (500 MHz, DMSO-d6): δ = 48.02 (C1-
allyl), 112.14 (C-4a), 116.09 (C-9), 117.43 (C3-allyl),
125.94 (C-7), 127.67 (C-8), 129.65 (C-6), 129.81 (C-
10), 129.84 (C-5), 129.94 (C-9a), 132.76 (C-5a),
136.01 (C2-allyl), 136.65 (C-10a), 159.70 (C-4), 175.53
(C-2).
acetate/hexane, 30:70) and cooled at room temperature.
The solvent was removed under reduced pressure and
the residue was treated with cold water. The solid
separated was collected by filtration and recrystallized
from ethanol to give the products 5a–e in quantitative
yields.
1
3-Methyl-2-ethylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin
-4-one (5a). Yield: 0.25 g (93%), mp: 62–64°C. MS: m/z:
270 (M+, 3%). Calculated for C15H14N2OS (270.35): C,
66.64; H, 5.22; N, 10.36. Found: C, 66.76; H, 5.43; N,
.
10.12. IR (KBr): ν 1666 (C¼O) cmꢀ1 1H-NMR
(500 MHz, CDCl3): δ = 1.36 (3H, t, J = 7.25 Hz,
SCH2CH3), 3.25 (2H, q, J = 7.25 Hz, SCH2CH3), 3.48
(3H, s, N3-CH3), 7.46 (1H, t, J = 7.25 Hz, H-8), 7.54
(1H, t, J = 7.50 Hz, H-7), 7.85 (1H, d, J = 8.00 Hz, H-9),
7.98 (1H, s, H-10), 8.00 (1H, d, J = 8.50 Hz, H-6), 8.77
(1H, s, H-5). 13C-NMR (500 MHz, CDCl3): δ = 14.36
(SCH2CH3), 26.34 (SCH2CH3), 26.37 (N3-CH3), 118.46
(C-4a), 123.42 (C-9), 125.74 (C-7), 127.76 (C-8),
128.37 (C-6), 128.60 (C-10), 129.50 (C-5), 131.03 (C-
9a), 136.87 (C-5a), 142.92 (C-10a), 155.47 (C-2), 161.98
(C-4).
3-Phenyl-2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-one
(4d). Yield: 1.30 g (43%), mp: 308–310°C. MS: m/z: 304
(M+, 4%). Calculated for C18H12N2OS (304.37): C, 71.03;
H, 3.97; N, 9.20. Found: C, 70.76; H, 4.05; N, 8.98. IR
(KBr): ν 3140 (NH), 1655 (C¼O), 1267 (C¼S) cmꢀ1
.
1H-NMR (500 MHz, DMSO-d6): δ = 7.32 (2H, d,
J = 7.50 Hz, H-2Ph, H-6Ph), 7.49 (4H, m, H-3Ph, H-4Ph,
H-5Ph, H-8), 7.64 (1H, t, J = 7.50 Hz, H-7), 7.84 (1H, s,
H-10), 7.95 (1H, d, J = 8.50 Hz, H-9), 8.12 (1H, d,
J = 8.50 Hz, H-6), 8.68 (1H, s, H-5), 13.00 (1H, s, NH).
13C-NMR (500 MHz, DMSO-d6): δ = 111.99 (C-4a),
116.70 (C-9), 120.90 (C-7), 126.06 (C-8), 127.74 (C4-
Ph), 128.48 (C-6), 128.99 (C-10), 129.28 (C2-Ph, C6-Ph),
129.68 (C3-Ph, C5-Ph), 129.80 (C-5), 130.04 (C-9a),
136.23 (C1-Ph), 136.75 (C-5a), 139.96 (C-10a), 160.39
(C-4), 176.50 (C-2).
3-Ethyl-2-ethylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin-
4-one (5b). Yield: 0.25 g (89%), mp: 82–84°C. MS: m/z:
284 (M+, 33%). Calculated for C9H8N2OS (284.38): C,
67.58; H, 5.67; N, 9.85. Found: C, 67.45; H, 5.78; N,
9.80. IR (KBr):
ν
.
1669 (C¼O) cmꢀ1 1H-NMR
(500 MHz, CDCl3): δ = 1.40 (3H, t, J = 7.25 Hz,
SCH2CH3), 1.47 (3H, t, J = 7.00 Hz, N3-CH2CH3), 3.17
(2H, q, J = 7.00 Hz, SCH2CH3), 4.20 (2H, q,
J = 7.50 Hz, N3-CH2CH3), 7.44 (1H, t, J = 7.25 Hz, H-
8), 7.50 (1H, t, J = 7.50 Hz, H-7), 7.87 (1H, d,
J = 8.00 Hz, H-9), 7.95 (1H, s, H-10), 7.97 (1H, d,
J = 8.50 Hz, H-6), 8.78 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 13.69 (SCH2CH3), 14.45
(NCH2CH3), 26.35 (SCH2CH3), 39.45 (NCH2CH3),
118.49 (C-4a), 122.99 (C-9), 125.54 (C-7), 127.67 (C-8),
128.15 (C-6), 128.27 (C-10), 129.33 (C-5), 130.87 (C-
9a), 136.73 (C-5a), 142.89 (C-10a), 155.59 (C-2), 161.08
(C-4).
3-(4-Methoxyphenyl)-2-thioxo-2,3-dihydro-1H-benzo[g]quin
azolin-4-one (4e). Yield 3.00 g (90%), mp: 302–304°C.
MS: m/z: 334 (M+, 4%). Calculated for C19H14N2O2S
(334.08): C, 68.24; H, 4.22; N, 8.38. Found: C, 68.66;
H, 4.24; N, 8.07. IR (KBr): ν 3164 (NH), 1663 (C¼O),
1266 (C¼S) cmꢀ1
.
1H-NMR (500 MHz, DMSO-d6):
δ = 3.83 (3H, s, OCH3), 7.03 (2H, d, J = 8.50 Hz, H-
3aryl, H-5aryl), 7.23 (2H, d, J = 9.00 Hz, H-2aryl, H-6aryl),
7.53 (1H, t, 7.50 Hz, H-8), 7.62 (1H, d,
J
=
J = 7.50 Hz, H-7), 7.70 (1H, s, H-10), 7.92 (1H, d,
J = 8.50 Hz, H-9), 8.24 (1H, d, J = 8.50 Hz, H-6), 8.70
(1H, s, H-5), 13.00 (1H, s, NH). 13C-NMR (500 MHz,
DMSO-d6): δ = 55.25 (OCH3), 115.04 (C3-aryl, C5-aryl),
119.64 (C-4a), 123.32 (C-9), 126.44 (C-7), 128.15 (C-8),
128.63 (C-6), 128.85 (C1-aryl), 128.99 (C-10), 129.12
(C-5), 130.97 (C-9a), 131.32 (C2-aryl, C6-aryl), 136.59
(C-5a), 143.11 (C-10a), 155.50 (C-4′), 158.71 (C-4),
176.15 (C-2).
3-Allyl-2-ethylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin-4
-one (5c). Yield: 0.28 g (95%), mp: 74–76°C. MS: m/z:
296 (M+, 18%). Calculated for C17H16N2OS (296.39): C,
68.89; H, 5.44; N, 9.45. Found: C, 68.52; H, 5.80; N,
9.12. IR (KBr):
ν
1681 (C¼O) cmꢀ1
.
1H-NMR
(500 MHz, CDCl3): δ = 1.50 (t, J = 7.00 Hz,
SCH2CH3), 3.36 (2H, q, J = 7.00 Hz, SCH2CH3), 4.83
(2H, d, J = 1.50 Hz, H-1allyl), 5.30 (2H, m, H-3allyl),
6.00 (1H, m, H-2allyl), 7.50 (1H, t, J = 7.00 Hz, H-8),
3-Substituted
2-ethylsulfanyl-2,3-dihydro-1H-benzo[g]
quinazolin-4-ones (5a–e). A mixture of 3-substituted 2-
thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones (4a–e)
(1 mmol), anhydrous acetonitrile (10 mL), and sodium
hydride (45 mg, 80%) was stirred at room temperature
for 1.5 h. Ethyl bromide (0.22 g, 2 mmol) was added
to the mixture with stirring at 40–50°C until the
starting material was consumed (8 h; TLC, ethyl
7.59 (1H, t,
J = 7.00 Hz, H-7), 7.94 (1H, d,
J = 8.50 Hz, H-9), 8.03 (2H, m, H-6, H-10), 8.85 (1H,
s, H-5). 13C-NMR (500 MHz, CDCl3): δ = 14.03
(SCH2CH3), 26.73 (SCH2CH3), 46.37 (C-1allyl), 118.26
(C-4a), 118.85 (C-3allyl), 123.41 (C-9), 125.71 (C-7),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. I. Khodair, M. A. Elsafi, and S. A. Al-Issa
Vol 000
127.73 (C-8), 128.35 (C-6), 128.59 (C-10), 129.42 (C-5),
130.98 (C-9a), 131.30 (C-2allyl), 136.88 (C-5a), 142.90
(C-10a), 155.45 (C-2), 161.90 (C-4).
3-Methyl-4-oxo-3,4-dihydro-benzo[g]quinazolin-2-ylsulfanyl
-acetic acid ethyl ester (5f). Yield: 0.28 g (85%), mp: 149–
151°C. MS: m/z: 328 (M+, 2%). Calculated for
C17H16N2O3S (328.39): C, 62.18; H, 4.91; N, 8.53.
Found: C, 62.55; H, 5.24; N, 8.31. IR (KBr): ν 1734
3-Phenyl-2-ethylsulfanyl-2,3-dihydro-1H-benzo[g]quinazolin
-4-one (5d). Yield: 0.26 g (79%), mp: 180–182°C. MS:
.
(COO), 1667 (C¼O) cmꢀ1 1H-NMR (500 MHz,
m/z: 332 (M+, 2%). Calculated for C20H16N2OS (332.42):
CDCl3): δ = 1.35 (3H, t, J = 7.00 Hz, OCH2CH3), 3.66
(3H, s, N3-CH3), 4.09 (2H, s, SCH2COO), 4.30 (2H, t,
J = 7.00 Hz, OCH2CH3), 7.49 (1H, t, J = 7.25 Hz, H-8),
7.57 (1H, t, J = 7.50 Hz, H-7), 7.91 (1H, d, J = 8.00 Hz,
H-9), 7.94 (1H, s, H-10), 8.01 (1H, d, J = 8.00 Hz, H-6),
8.80 (1H, s, H-5). 13C-NMR (DMSO-d6): δ = 14.30
(OCH2CH3), 30.23 (N3-CH3), 34.16 (SCH2COO), 61.96
(OCH2CH3), 118.52 (C-4a), 123.18 (C-9), 125.83 (C-7),
127.73 (C-8), 128.39 (C-6), 128.55 (C-10), 129.40 (C-5),
131.05 (C-9a), 136.71 (C-5a), 142.43 (C-10a), 154.40 (C-
2), 162.00 (C-4), 168.60 (COO).
C, 72.26; H, 4.85; N, 8.43. Found: C, 72.04; H, 5.16; N,
8.22. IR (KBr):
ν
.
1696 (C¼O) cmꢀ1 1H-NMR
(500 MHz, DMSO-d6): δ = 1.27 (t, J = 7.25 Hz,
SCH2CH3), 3.12 (2H, q, J = 7.25 Hz, SCH2CH3), 7.41
(2H, d, J = 7.50 Hz, H-2Ph, H-6Ph), 7.52 (1H, t,
J = 7.50 Hz, H-8), 7.62 (3H, m, H-3Ph, H-4Ph, H-5Ph),
7.68 (1H, t, J = 7.50 Hz, H-7), 7.91 (1H, s, H-10), 8.03
(1H, d, J = 8.50 Hz, H-9), 8.12 (1H, d, J = 8.50 Hz, H-
6), 8.88 (1H, s, H-5). 13C-NMR (500 MHz, CDCl3):
δ = 14.33 (SCH2CH3), 26.80 (SCH2CH3), 119.64 (C-4a),
123.39 (C-9), 126.49 (C-7), 128.49 (C-8), 128.17 (C-
4Ph), 128.62 (C-6), 129.17 (C-10), 129.72 (C-2Ph, C-6Ph),
129.83 (C-3Ph, C-5Ph), 130.15 (C-5), 130.46 (C-9a),
136.52 (C-1Ph), 136.98 (C-5a), 143.21 (C-10a), 156.72
(C-2), 161.50 (C-4).
3-Ethyl-4-oxo-3,4-dihydro-benzo[g]quinazolin-2-ylsulfanyl-
acetic acid ethyl ester (5g). Yield: 0.30 g (88%), mp: 116–
118°C. MS: m/z: 342 (M+, 2%). Calculated for
C18H18N2O3S (342.41): C, 63.14; H, 5.30; N, 8.18.
Found: C, 63.01; H, 5.44; N, 8.00. IR (KBr): ν 1735
3-(4-Methoxyphenyl)-2-ethylsulfanyl-2,3-dihydro-1H-benzo
(COO), 1683 (C¼O) cmꢀ1
.
1H-NMR (500 MHz,
[g]quinazolin-4-one (5e). Yield: 0.32 g (89%), mp: 186–
188°C. MS: m/z: 362 (M+, 5%). Calculated for
C21H18N2O2S (362.45): C, 69.59; H, 5.01; N, 7.73.
Found: C, 69.23; H, 5.27; N, 8.04. IR (KBr): ν 1696
DMSO-d6): δ = 1.22 (3H, t, J = 7.00 Hz, N3CH2CH3),
1.32 (3H, t, J = 7.00 Hz, OCH2CH3), 4.17 (6H, m,
SCH2COO, N3-CH2CH3, OCH2CH3), 7.58 (1H, t,
J = 7.50 Hz, H-8), 7.69 (1H, d, J = 8.00 Hz, H-7), 7.98
(1H, s, H-10), 8.09 (1H, d, J = 7.50 Hz, H-9), 8.16 (1H,
d, J = 7.50 Hz, H-6), 8.79 (1H, d, J = 7.50 Hz, H-5).
(C¼O) cmꢀ1
.
1H-NMR (500 MHz, DMSO-d6):
δ = 1.31 (t, J = 7.25 Hz, SCH2CH3), 3.15 (2H, q,
J = 7.25 Hz, SCH2CH3), 3.80 (1H, s, OCH3), 7.12
(3H, 2H, d, J = 8.50 Hz, H-3aryl, H-5aryl), 7.39 (2H, d,
J = 8.50 Hz, H-2aryl, H-6aryl), 7.55 (1H, t, J = 7.50 Hz,
H-8), 7.69 (1H, t, J = 7.50 Hz, H-7), 8.12 (1H, s, H-
10), 8.15 (1H, d, J = 8.50 Hz, H-9), 8.23 (1H, d,
J = 8.50 Hz, H-6), 8.88 (1H, s, H-5). 13C-NMR
(500 MHz, DMSO-d6): δ = 14.31 (SCH2CH3), 26.75
(SCH2CH3), 55.57 (OCH3), 114.99 (C-3aryl, C-5aryl),
119.70 (C-4a), 123.50 (C-9), 126.42 (C-7), 128.02 (C-
8), 128.15 (C-6), 128.61 (C-1aryl), 129.12 (C-10),
129.79 (C-5), 131.15 (C-9a), 131.30 (C-2aryl, C-6aryl),
136.85 (C-5a), 143.50 (C-10a), 155.50 (C-2), 160.75
(C-4aryl), 162.20 (C-4).
13C-NMR (500 MHz, DMSO-d6):
δ
=
13.73
(N3CH2CH3), 14.61 (OCH2CH3), 34.49 (SCH2COO),
61.64 (OCH2CH3), 118.85 (C-4a), 123.15 (C-9), 126.56
(C-7), 128.15 (C-6), 128.48 (C-8), 129.17 (C-10), 129.77
(C-5), 131.03 (C-9a), 136.76 (C-5a), 142.48 (C-10a),
154.94 (C-2), 161.02 (C-4), 168.80 (COO).
3-Allyl-4-oxo-3,4-dihydro-benzo[g]quinazolin-2-ylsulfanyl-
acetic acid ethyl ester (5h). Yield: 0.29 g (83%), mp: 138–
140°C. MS: m/z: 354 (M+, 2%). Calculated for
C19H18N2O3S (354.42): C, 64.39; H, 5.12; N, 7.90.
Found: C, 64.18; H, 5.29; N, 7.82. IR (KBr): ν 1734
.
(COO), 1683 (C¼O) cmꢀ1 1H-NMR (500 MHz,
CDCl3): δ = 1.34 (3H, t, J = 7.00 Hz, OCH2CH3), 4.10
(6H, m, SCH2COO), 4.29 (2H, q, J = 7.75 Hz,
OCH2CH3), 4.70 (2H, m, H-1allyl), 5.33 (2H, m, H-3allyl),
6.01 (1H, m, H-2allyl), 7.50 (1H, t, J = 7.25 Hz, H-8),
7.60 (1H, t, J = 7.25 Hz, H-7), 7.98 (1H, d, J = 8.50 Hz,
H-9), 8.00 (1H, s, H-10), 8.04 (1H, d, J = 8.50 Hz, H-6),
8.85 (1H, s, H-5). 13C-NMR (500 MHz, DMSO-d6):
δ = 14.62 (OCH2CH3), 34.58 (SCH2COO), 46.22 (C1-
allyl), 61.60 (OCH2CH3), 117.93 (C-4a), 118.71 (C3-
allyl), 123.23 (C-9), 126.58 (C-7), 128.17 (C-8), 128.66
(C-6), 129.22 (C-10), 129.78 (C-5), 131.05 (C-9a),
132.05 (C2-allyl), 136.82 (C-5a), 142.44 (C-10a), 155.30
(C-2), 161.80 (C-4), 168.70 (COO).
3-Substituted
4-oxo-3,4-dihydro-benzo[g]quinazolin-2-
ylsulfanyl-acetic acid ethyl esters (5f–j).
A mixture of
4a–e (1 mmol), anhydrous acetonitrile (10 mL), and
sodium hydride (45 mg, 80%) was stirred at room
temperature for 1.5 h. Ethyl bromoacetate (0.33 g,
2 mmol) was added to the mixture with stirring at 40–
50°C until the starting material was consumed (8 h; TLC,
ethyl acetate/hexane, 30:70) and cooled at room
temperature. The solvent was removed under reduced
pressure and the residue was treated with cold water. The
solid separated was collected by filtration and
recrystallized from ethanol to give the products 5f–j in
quantitative yields.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-
benzo[g]quinazolin-4-ones and Their Reactions with Alkyl Halides and α-
Glycopyranosyl Bromides
3-Phenyl-4-oxo-3,4-dihydro-benzo[g]quinazolin-2-ylsulfanyl
(300.38): C, 63.98; H, 5.37; N, 9.33. Found: C, 63.90; H,
1
5.08; N, 9.26. IR (KBr): ν 1663 (C¼O) cmꢀ1. H-NMR
-acetic acid ethyl ester (5i). Yield: 0.30 g (78%), mp: 178–
180°C. MS: m/z: 390 (M+, 3%). Calculated for
C22H18N2O3S (390.46): C, 67.67; H, 4.65; N, 7.17.
Found: C, 67.60; H, 4.84; N, 7.28. IR (KBr): ν 1736
(500 MHz, DMSO-d6): δ = 3.40 (3H, s, N3-CH3), 3.59
(2H, t, J = 5.25 Hz, SCH2), 3.67 (3H, s, OCH3), 3.81
(2H, t, J = 6.25 Hz, OCH2), 7.50 (1H, t, J = 7.25 Hz, H-
8), 7.59 (1H, t, J = 7.25 Hz, H-7), 7.94 (1H, d,
J = 8.00 Hz, H-9), 7.98 (1H, s, H-10), 8.03 (1H, d,
J = 8.00 Hz, H-6), 8.80 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 30.14 (SCH2), 31.40 (N3-CH3),
58.86 (OCH3), 70.67 (OCH2), 118.69 (C-4a), 123.08 (C-
9), 125.71 (C-7), 127.70 (C-8), 128.34 (C-6), 128.53 (C-
10), 129.41 (C-5), 131.00 (C-9a), 136.80 (C-5a), 142.77
(C-10a), 155.50 (C-2), 162.20 (C-4).
(COO), 1697 (C¼O) cmꢀ1
.
1H-NMR (500 MHz,
CDCl3): δ = 1.35 (3H, t, J = 7.25 Hz, OCH2CH3), 3.98
(2H, s, SCH2COO), 4.28 (2H, q, J = 7.25 Hz,
OCH2CH3), 7.44 (2H, d, J = 7.50 Hz, H-2Ph, H-6Ph),
7.53 (1H, t, J = 7.50 Hz, H-8), 7.59 (4H, m, H-3Ph, H-
4Ph, H-5Ph, H-7), 7.98 (1H, m, H-H, H-10), 8.05 (1H, d,
J = 8.50 Hz, H-6), 8.87 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 14.29 (OCH2CH3), 35.04
(SCH2COO), 61.82 (OCH2CH3), 119.10 (C-4a), 123.49
(C-9), 126.05 (C-7), 127.83 (C-8), 128.64 (C4-Ph),
129.02 (C-6), 129.27 (C-10), 129.47 (C2-Ph, C6-Ph),
129.76 (C3-Ph, C5-Ph), 130.18 (C-5), 131.18 (C-9a),
135.62 (C-1Ph), 136.47 (C-5a), 142.72 (C-10a), 156.72
(C-2), 161.50 (C-4).
3-Ethyl-2-ethoxymethylsulfanyl-2,3-dihydro-1H-benzo[g]qui
nazolin-4-one (5l). Yield: 1.22 g (78%), mp: 54–56°C.
MS: m/z: 314 (M+, 5%). Calculated for C17H18N2O2S
(314.40): C, 64.94; H, 5.77; N, 8.91. Found: C, 64.63; H,
1
5.60; N, 8.82. IR (KBr): ν 1670 (C¼O) cmꢀ1. H-NMR
(500 MHz, CD3COCD3-d6): δ = 1.36 (3H, t, J = 7.00 Hz,
N3-CH2CH3), 3.56 (2H, t, J = 6.25 Hz, SCH2), 3.64 (3H,
s, OCH3), 3.76 (2H, t, J = 6.25 Hz, OCH2), 4.19 (2H, t,
J = 7.00 Hz, N3-CH2CH3), 7.54 (1H, t, J = 7.25 Hz, H-
8), 7.56 (1H, t, J = 7.25 Hz, H-7), 7.92 (1H, d,
J = 8.00 Hz, H-9), 7.96 (1H, s, H-10), 8.01 (1H, d,
J = 8.00 Hz, H-6), 8.76 (1H, s, H-5). 13C-NMR
(500 MHz, CD3COCD3-d6): δ = 13.20 (N3-CH2CH3),
31.00 (SCH2), 39.90 (N3-CH2CH3), 58.00 (OCH3), 71.00
(OCH2), 119.00 (C-4a), 123.00 (C-9), 126.00 (C-7),
127.50 (C-8), 128.00 (C-6), 128.50 (C-10), 129.00 (C-5),
131.00 (C-9a), 136.00 (C-5a), 143.00 (C-10a), 155.00 (C-
2), 161.00 (C-4).
3-(4-Methoxyphenyl)-4-oxo-3,4-dihydro-benzo[g]quinazolin-
2-ylsulfanyl-acetic acid ethyl ester (5j). Yield: 0.29 g (69%),
mp: 149–151°C. MS: m/z: 420 (M+, 3%). Calculated for
C23H20N2O4S (420.48): C, 65.70; H, 4.79; N, 6.66.
Found: C, 65.57; H, 4.84; N, 6.62. IR (KBr): ν 1735
(COO), 1697 (C¼O) cmꢀ1. 1H-NMR (500 MHz, CDCl3):
δ = 1.34 (t, J = 7.25 Hz, OCH2CH3), 3.86 (3H, s, OCH3),
3.90 (2H, s, 2H, s, SCH2COO), 4.28 (2H, q, J = 7.25 Hz,
OCH2CH3), 7.09 (3H, 2H, d, J = 8.50 Hz, H-3aryl, H-
5
aryl), 7.34 (2H, d, J = 8.50 Hz, H-2aryl, H-6aryl), 7.52 (1H,
t, J = 7.50 Hz, H-8), 7.62 (1H, t, J = 7.50 Hz, H-7), 7.96
(1H, s, H-10), 8.03 (1H, d, J = 8.50 Hz, H-9), 8.24 (1H, d,
J = 8.50 Hz, H-6), 8.90 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 14.31 (OCH2CH3), 35.09
(SCH2COO), 55.57 (OCH3), 61.80 (OCH2CH3), 114.99
(C3-aryl, C5-aryl), 119.15 (C-4a), 123.46 (C-9), 125.99
(C-7), 127.81 (C-8), 128.02 (C-6), 128.59 (C1-aryl),
129.00 (C-10), 129.49 (C-5), 130.58 (C-9a), 131.14 (C2-
aryl, C6-aryl), 136.94 (C-5a), 142.81 (C-10a), 155.54 (C-
2), 160.80 (C4-aryl), 162.20 (C-4), 168.80 (COO).
3-Allyl-2-ethoxymethylsulfanyl-2,3-dihydro-1H-benzo[g]qui
nazolin-4-one (5m). Yield: 0.90 g (55%), mp: 62–64°C.
MS: m/z: 326 (M+, 2%). Calculated for C18H18N2O2S
(326.41): C, 66.23; H, 5.56; N, 8.58. Found: C, 66.06; H,
1
5.44; N, 8.67. IR (KBr): ν 1691 (C¼O) cmꢀ1. H-NMR
(500 MHz, CD3COCD3-d6): δ = 3.57 (2H, t, J = 6.30 Hz,
SCH2), 3.64 (3H, s, OCH3), 3.75 (2H, t, J = 6.30 Hz,
OCH2), 4.80 (2H, d, J = 5.00 Hz, H-1allyl), 5.24 (2H, m,
H-3allyl), 6.01 (1H, m, H-2allyl), 7.56 (1H, t, J = 7.25 Hz,
H-8), 7.65 (1H, t, J = 7.25 Hz, H-7), 8.06 (1H, d,
J = 8.00 Hz, H-9), 8.45 (1H, s, H-10), 8.50 (1H, d,
J = 8.00 Hz, H-6), 8.80 (1H, s, H-5). 13C-NMR
(500 MHz, CD3COCD3-d6): δ = 31.00 (SCH2), 45.90
(C1-allyl), 58.00 (OCH3), 70.20 (OCH2), 119.21 (C-4a),
120.21 (C3-allyl), 121.91 (C-9), 122.02 (C-7), 128.63 (C-
8), 129.21 (C-6), 129.32 (C-10), 131.52 (C-5), 132.05
(C-9a), 135.81 (C-5a), 136.02 (C2-allyl), 142.45 (C-10a),
155.00 (C-2), 161.00 (C-4).
3-Substituted 2-ethoxymethylsulfanyl-2,3-dihydro-1H-ben
zo[g]quinazolin-4-ones (5k–o).
A mixture of 4a–e
(5 mmol), anhydrous dimethylformamide (10 mL), and
potassium carbonate (0.83 g, 6 mmol) was stirred at room
temperature for 1.5 h. 1-Chloro-2-methoxyethane (0.54 g,
6 mmol) was added to the mixture with stirring 90–
100°C until the starting material was consumed (2 h;
TLC, ethyl acetate/hexane, 50:50) and cooled at room
temperature. The mixture was poured into cold water,
and the solid separated was collected by filtration and
recrystallized from cyclohexane to give the products 5f–j
in quantitative yields.
3-Phenyl-2-ethoxymethylsulfanyl-2,3-dihydro-1H-benzo[g]
quinazolin-4-one (5n).
Yield: 1.10 g (61%), mp: 154–
156°C. MS: m/z: 362 (M+, 2%). Calculated for
C21H18N2O2S (362.45): C, 69.59; H, 5.01; N, 7.73.
Found: C, 69.32; H, 5.14; N, 8.01. IR (KBr): ν 1696
3-Methyl-2-ethoxymethylsulfanyl-2,3-dihydro-1H-benzo[g]
quinazolin-4-one (5k). Yield: 1.18 g (78%), mp: 90–92°C.
MS: m/z: 300 (M+, 5%). Calculated for C16H16N2O2S
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. I. Khodair, M. A. Elsafi, and S. A. Al-Issa
Vol 000
1
(C¼O) cmꢀ1. H-NMR (500 MHz, CDCl3): δ = 3.46 (t,
(500 MHz, CDCl3): δ = 1.97 (3H, s, Ac), 2.03 (3H, s,
Ac), 2.04 (3H, s, Ac), 2.10 (3H, s, Ac), 3.63 (3H, s, N3-
CH3), 4.11 (1H, m, H-6′), 4.27 (2H, m, H-5′, H-6″), 5.22
(1H, t, J = 9.50 Hz, H-4′), 5.38 (1H, d, J = 9.50 Hz, H-
2′), 5.48 (1H, d, J = 9.50 Hz, H-3′), 6.08 (1H, d,
2J1′,2′ = 10.50 Hz, H-1′), 7.55 (1H, t, J = 7.50 Hz, H-8),
7.64 (1H, t, J = 7.50 Hz, H-7), 8.05 (1H, s, H-10), 8.06
(1H, d, J = 8.50 Hz, H-6, H-9), 8.87 (1H, s, H-5). 13C-
NMR (500 MHz, CDCl3): δ = 20.62, 20.65 (4Ac), 30.31
(N3-CH3), 62.04 (C-6′), 68.33 (C-2′), 68.80 (C-3′), 74.14
(C-4′), 76.53 (C-5′), 82.37 (C-1′), 119.56 (C-4a), 123.52
(C-9), 125.85 (C-7), 126.15 (C-8), 127.70 (C-6), 128.70
(C-10), 129.52 (C-5), 131.28 (C-9a), 136.02 (C-5a),
142.43 (C-10a), 153.00 (C-2), 162.25 (C-4), 169.63,
170.30, 170.70 (4Ac).
J = 6.30 Hz, SCH2), 3.70 (2H, q, J = 6.30 Hz, OCH2),
7.39 (2H, d, J = 7.50 Hz, H-2Ph, H-6Ph), 7.53 (1H, t,
J = 7.50 Hz, H-8), 7.57 (3H, m, H-3Ph, H-4Ph, H-5Ph),
7.62 (1H, t, J = 7.50 Hz, H-7), 7.97 (1H, s, H-10), 8.05
(1H, d, J = 8.50 Hz, H-9), 8.10 (1H, d, J = 8.50 Hz, H-
6), 8.80 (1H, s, H-5). 13C-NMR (500 MHz, CDCl3):
δ = 14.33 (SCH2CH3), 26.80 (SCH2CH3), 119.64 (C-4a),
123.39 (C-9), 126.49 (C-7), 128.49 (C-8), 128.17 (C4-
Ph), 128.62 (C-6), 129.17 (C-10), 129.72 (C2-Ph, C6-Ph),
129.83 (C3-Ph, C5-Ph), 130.15 (C-5), 130.46 (C-9a),
136.52 (C1-Ph), 136.98 (C-5a), 143.21 (C-10a), 156.72
(C-2), 161.50 (C-4).
3-(4-Methoxyphenyl)-2-ethoxymethylsulfanyl-2,3-dihydro-1
H-benzo[g]quinazolin-4-one (5o). Yield: 1.28 g (65%), mp:
158–160°C. MS: m/z: 392 (M+, 2%). Calculated for
C22H20N2O3S (392.47): C, 67.33; H, 5.14; N, 7.14; S,
8.17. Found: C, 67.26; H, 5.32; N, 7.27. IR (KBr): ν
3-Ethyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylsulfa
nyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-one (8b).
Yield:
2.50 g (85%), mp: 164–166°C. MS: m/z: 586 (M+, 1%).
Calculated for C28H30N2O10S (586.61): C, 57.33; H,
5.15; N, 4.78. Found: C, 57.23; H, 5.26; N, 4.48. IR
1695 (C¼O) cmꢀ1
.
1H-NMR (500 MHz, CDCl3):
δ = 3.40 (3H, br. s, OCH3), 3.50 (2H, t, J = 6.00 Hz,
SCH2), 3.70 (3H, J = 6.00 Hz, OCH2), 3.90 (3H, s,
OCH3), 7.08 (2H, d, J = 7.50 Hz, H-3aryl, H-5aryl), 7.29
(2H, d, J = 7.50 Hz, H-2aryl, H-6aryl), 7.54 (1H, t,
J = 7.50 Hz, H-8), 7.63 (1H, d, J = 8.50 Hz, H-7), 7.99
(1H, d, J = 8.50 Hz, H-9), 8.05 (1H, d, J = 8.50 Hz, H-
6), 8.19 (1H, s, H-10), 8.88 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 31.95 (SCH2), 55.95 (OCH3),
58.36 (OCH3), 70.36 (OCH2), 115.04 (C3-aryl, C5-aryl),
119.64 (C-4a), 123.32 (C-9), 126.44 (C-7), 128.15 (C-8),
128.63 (C-6), 128.85 (C1-aryl), 129.12 (C-10), 129.78
(C-5), 130.97 (C-9a), 131.32 (C2-aryl, C6-aryl), 136.95
(C-5a), 143.11 (C-10a), 157.20 (C-2), 160.51 (C4-aryl),
161.65 (C-4).
(KBr): ν 1752 (C¼O), 1684 (C¼O) cmꢀ1
.
1H-NMR
(500 MHz, CDCl3): δ = 1.40 (3H, t, J = 7.05 Hz, N3-
CH2CH3), 1.93 (3H, s, Ac), 2.01 (3H, s, Ac), 2.03 (3H, s,
Ac), 2.12 (3H, s, Ac), 4.09 (1H, m, H-6′), 4.19 (3H, m,
N3-CH2CH3, H-5′), 4.28 (1H, m, H-6′), 5.20 (1H, t,
J = 9.50 Hz, H-4′), 5.35 (1H, d, J = 9.50 Hz, H-2′), 5.48
(1H, d,
J
=
9.50 Hz, H-3′), 6.07 (1H, d,
2J1′,2′ = 10.50 Hz, H-1′), 7.55 (1H, d, J = 7.50 Hz, H-8),
7.63 (1H, t, J = 7.50 Hz, H-7), 7.90 (1H, d, J = 8.50 Hz,
H-9), 8.02 (1H, s, H-10), 8.05 (1H, d, J = 8.5 Hz, H-6),
8.80 (1H, s, H-5). 13C-NMR (500 MHz, CDCl3):
δ = 13.69 (N3-CH2CH3), 20.66 (4Ac), 39.77 (N3-
CH2CH3), 62.04 (C-6′), 68.03 (C-2′), 68.87 (C-3′), 74.15
(C-4′), 76.52 (C-5′), 82.64 (C-1′), 118.96 (C-4a), 123.54
(C-9), 126.13 (C-7), 127.69 (C-8), 128.58 (C-6), 128.60
(C-10), 129.50 (C-5), 131.28 (C-9a), 136.76 (C-5a),
142.40 (C-10a), 151.70 (C-2), 161.75 (C-4), 169.52,
169.63, 170.18, 170.70 (4Ac).
3-Substituted 2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyrano
sylsulfanyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-ones (8a–
h).
The nucleoside bases 4a–e (5 mmol) was
suspended in anhydrous acetonitrile (25 mL) at room
temperature. To this suspension was added NaH (80%,
0.15 g, 5 mmol), and the mixture was stirred at room
temperature for 1.5 h. 2′,3′,4′,6′-Tetra-O-acetyl-α-D-
glycopyranosylsulfanyl bromides (6a,b, 2.66 g,
5.50 mmol) was added, and the mixture was stirred at
room temperature for 12 h until the starting material was
consumed (TLC, CH2Cl2/MeOH, 98:2). The solvent was
removed under reduced pressure and then treated with
water. The solid separated was collected by filtration and
recrystallized from ethanol to give the products 8a–h in
quantitative yields.
3-Allyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylsulfan
yl)-2,3-dihydro-1H-benzo[g]quinazolin-4-one (8c).
Yield:
2.68 g (89%), mp: 166–168°C. MS: m/z: 598 (M+, 1%).
Calculated for C29H30N2O10S (598.62): C, 58.19; H,
5.05; N, 4.68. Found: C, 57.95; H, 4.70; N, 4.57. IR
(KBr): ν 1751 (C¼O), 1682 (C¼O) cmꢀ1
.
1H-NMR
(500 MHz, CDCl3): δ = 1.90 (3H, s, Ac), 2.02 (3H, s,
Ac), 2.05 (3H, s, Ac), 2.10 (3H, s, Ac), 4.09 (1H, m, H-
6′), 4.19 (1H, dd, J = 1.50, 11.00 Hz, H-5′), 4.28 (1H,
dd, J = 5.00, 12.50 Hz, H-6″), 4.60 (2H, dd, J = 5.50,
11.50 Hz, H-1allyl), 4.80 (2H, dd, J = 5.50, 11.50 Hz, H-
3allyl), 5.20 (1H, t, J = 9.50 Hz, H-4′), 5.33 (1H, d,
J = 9.50 Hz, H-2′), 5.47 (1H, d, J = 9.50 Hz, H-3′), 5.59
3-Methyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylsulf
anyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-one (8a). Yield:
1.81 g (63%), mp: 190–192°C. MS: m/z: 572 (M+, 1%).
Calculated for C27H28N2O10S (572.58): C, 59.64; H,
4.93; N, 4.89. Found: C, 59.28; H, 4.82; N, 4.85. IR
2
(1H, m, H-2allyl), 6.04 (1H, d, J1′,2′ = 10.50 Hz, H-1′),
7.55 (1H, d, J = 7.50 Hz, H-8), 7.64 (1H, t, J = 7.50 Hz,
H-7), 7.90 (1H, d, J = 8.50 Hz, H-9), 8.04 (1H, s, H-10),
(KBr): ν 1761 (C¼O), 1675 (C¼O) cmꢀ1
.
1H-NMR
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-
benzo[g]quinazolin-4-ones and Their Reactions with Alkyl Halides and α-
Glycopyranosyl Bromides
8.05 (1H, d, J = 8.5 Hz, H-6), 8.80 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 20.63 (4Ac), 46.18 (C-1allyl),
62.05 (C-6′), 68.40 (C-2′), 68.88 (C-3′), 74.11 (C-4′),
76.54 (C-5′), 82.79 (C-1′), 118.83 (C-3allyl), 123.64 (C-
4a), 126.19 (C-9), 127.71 (C-7), 128.74 (C-8), 129.51 (C-
6, C-10), 130.79 (C-5), 131.32 (C-9a), 136.93 (C-2allyl
C-5a), 142.35 (C-10a), 151.94 (C-2), 161.71 (C-4),
169.49, 169.53, 170.14, 170.65 (4Ac).
10a), 153.53 (C-2), 160.85 (C-4aryl), 162.25 (C-4),
169.36, 169.46, 170.19, 170.69 (4Ac).
3-Methyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosylsu
lfanyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-ones (8f).
Yield: 1.86 g (65%), mp: 168–170°C. MS: m/z: 572 (M+,
2%). Calculated for C27H28N2O10S (572.58): C, 59.64;
H, 4.93; N, 4.89. Found: C, 59.50; H, 4.78; N, 4.54. IR
,
(KBr): ν 1752 (C¼O), 1686 (C¼O) cmꢀ1
.
1H-NMR
(500 MHz, CDCl3): δ = 1.88 (3H, s, Ac), 2.05 (3H, s,
Ac), 2.012 (3H, s, Ac), 2.22 (3H, s, Ac), 3.65 (3H, s, N3-
CH3), 4.13 (1H, m, H-6′), 4.22 (2H, m, H-5′), 4.29 (1H,
m, H-6″), 5.31 (1H, dd, J = 3.00, 9.50 Hz, H-4′), 5.50
3-Phenyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosylsulf
anyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-one (8d). Yield:
1.85 g (58%), mp: 108–110°C. MS: m/z: 634 (M+, 1%).
Calculated for C32H30N2O10S (634.65): C, 60.56; H,
4.76; N, 4.41. Found: C, 60.37; H, 4.78; N, 4.15. IR
2
(1H, m, 2′-H, H-3′), 6.07 (1H, d, J1′,2′ = 10.50 Hz, H-
(KBr): ν 1751 (C¼O), 1699 (C¼O) cmꢀ1
.
1H-NMR
1′), 7.55 (1H, t, J = 7.50 Hz, H-8), 7.64 (1H, t,
J = 7.50 Hz, H-7), 7.99 (1H, d, J = 8.50 Hz, H-9), 8.09
(2H, s, H-6, H-10), 8.80 (1H, s, H-5). 13C-NMR
(500 MHz, CDCl3): δ = 20.61, 20.71 (4Ac), 30.29 (N3-
CH3), 61.65 (C-6′), 66.21 (C-2′), 67.46 (C-3′), 72.12 (C-
4′), 75.25 (C-5′), 82.83 (C-1′), 118.71 (C-4a), 123.61 (C-
9), 126.13 (C-7), 127.73 (C-8), 128.67 (C-6), 128.73 (C-
10), 129.49 (C-5), 131.27 (C-9a), 136.76 (C-5a), 142.37
(C-10a), 152.26 (C-2), 162.16 (C-4), 169.84, 169.98,
170.27, 170.47 (4Ac).
(500 MHz, CDCl3): δ = 1.92 (3H, s, Ac), 1.99 (3H, s,
Ac), 2.01 (3H, s, Ac), 2.07 (3H, s, Ac), 4.11 (1H, m, H-
6′), 4.17 (1H, d, J = 12.50 Hz, H-5′), 4.27 (1H, d,
J = 12.50 Hz, H-6″), 5.12 (1H, m, H-2′, H-4′), 5.38 (1H,
2
t, J = 9.50 Hz, H-3′), 5.88 (1H, d, J1′,2′ = 10.50 Hz, H-
1′), 7.25 (2H, m, H-2Ph, H-6Ph), 7.38 (1H, d,
J = 7.50 Hz, H-8), 7.47 (1H, t, J = 7.50 Hz, H-7), 7.56
(3H, m, H-3Ph, H-4Ph, H-5Ph), 7.64 (1H, d, J = 8.50 Hz,
H-9), 7.78 (1H, s, H-10), 8.29 (1H, d, J = 8.5 Hz, H-6),
8.82 (1H, s, H-5). 13C-NMR (500 MHz, CDCl3):
δ = 20.61, 20.70 (4Ac), 61.95 (C-6′), 68.21 (C-2′), 68.81
(C-3′), 74.20 (C-4′), 76.39 (C-5′), 82.40 (C-1′), 119.08
(C-4a), 123.85 (C-9), 126.29 (C-7), 127.69 (C-8), 128.82
(C-4Ph), 128.86 (C-6), 129.10 (C-10), 129.20 (C-3Ph),
129.38 (C-5Ph), 129.54 (C-2Ph), 129.67 (C-6Ph), 130.31
(C-5), 131.15 (C-9a), 135.15 (C-1Ph), 136.79 (C-5a),
142.45 (C-10), 152.57 (C-2), 161.77 (C-4), 169.15,
169.39, 169.90, 170.45 (4Ac).
3-Allyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosylsulf
anyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-ones
(8g).
Yield: 1.89 g (63%), mp: 116–118°C. MS: m/z: 598 (M+,
1%). Calculated for C29H30N2O10S (598.62): C, 58.19;
H, 5.05; N, 4.68. Found: C, 58.02; H, 5.27; N, 4.68. IR
(KBr): ν 1743 (C¼O), 1686 (C¼O) cmꢀ1
.
1H-NMR
(500 MHz, CDCl3): δ = 1.91 (3H, s, Ac), 2.03 (3H, s,
Ac), 2.06 (3H, s, Ac), 2.20 (3H, s, Ac), 4.10–4.30 (3H,
m, H-5′, H-6′, H-6″), 4.70 (1H, dd, J = 5.50, 11.50 Hz,
H-4′), 4.88 (1H, d, J = 9.50 Hz, H-2′), 5.15–5.49 (4H, m,
H-1allyl, H-3allyl), 5.47 (1H, t, J = 9.50 Hz, H-3′), 5.95
3-(4-Methoxyphenyl)-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucop
yranosylsulfanyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-one
(8e). Yield: 3.20 g (96%), mp: 151–158°C. MS: m/z: 664
2
(1H, m, H-2allyl), 6.04 (1H, d, J1′,2′ = 10.50 Hz, H-1′),
(M+). Calculated for C33H32N2O11S (664.68): C, 59.63; H,
4.85; N, 4.21. Found: C, 59.48; H, 4.88; N, 4.35. IR (KBr):
7.50 (1H, d, J = 7.50 Hz, H-8), 7.64 (1H, t, J = 7.50 Hz,
H-7), 7.99 (1H, d, J = 8.50 Hz, H-9), 8.00 (1H, m, H-H,
H-10), 8.80 (1H, s, H-5). 13C-NMR (500 MHz, CDCl3):
δ = 20.64, 20.73 (4Ac), 46.17 (C-1allyl), 61.58 (C-6′),
66.27 (C-2′), 67.44 (C-3′), 72.10 (C-4′), 75.23 (C-5′),
83.26 (C-1′), 118.83 (C-3allyl), 123.70 (C-4a), 126.20 (C-
9), 127.77 (C-7), 128.74 (C-8), 128.86 (C-6), 129.51 (C-
10), 130.84 (C-5), 131.31 (C-9a), 136.84 (C-2allyl, C-5a),
142.35 (C-10a), 151.94 (C-2), 161.78 (C-4), 169.79,
170.02, 170.29, 170.48 (4Ac).
ν 1694 (C¼O), 1755 (C¼O) cmꢀ1. H-NMR (500 MHz,
1
CDCl3): δ = 1.96 (3H, s, Ac), 2.03 (3H, s, Ac), 2.05 (3H,
s, Ac), 2.13 (3H, s, Ac), 3.92 (3H, s, OCH3), 4.07 (1H,
m, H-6′), 4.21 (1H, m, H-6″), 4.28 (1H, dd, J = 5.00,
12.50, H-5′), 5.17 (2H, m, H-2′, H-3′, H-4′), 5.85 (1H, d,
J = 11.00 Hz, H-1′), 7.06 (2H, d, J = 8.50 Hz, H-3aryl, H-
5aryl), 7.20 (1H, d, J = 8.50 Hz, H-2aryl), 7.34 (1H, d,
J = 8.50 Hz, H-6aryl), 7.56 (1H, t, J = 7.25 Hz, H-8),
7.66 (1H, t, J = 7.25 Hz, H-7), 8.02 (1H, d, J = 8.50 Hz,
H-9), 8.08 (1H, d, J = 8.50 Hz, H-6), 8.09 (1H, s, H-10),
8.89 (1H, s, H-5). 13C-NMR (500 MHz, CDCl3):
δ = 20.62, 20.68 (4Ac), 55.54 (OCH3), 62.04 (C-6′),
68.31 (C-2′), 68.91 (C-3′), 74.32 (C-4′), 76.47 (C-5′),
82.52 (C-1′), 115.23 (C-3aryl, H-5aryl), 119.25 (C-4a),
123.76 (C-9), 126.23 (C-7), 127.50 (C-8), 128.82 (C-6),
129.15 (C-1aryl), 129.56 (C-10), 129.56 (C-5), 130.57 (C-
3-Phenyl-2-(2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosylsu
lfanyl)-2,3-dihydro-1H-benzo[g]quinazolin-4-one (8h).
Yield: 1.2.70 g (85%), mp: 82–84°C. MS: m/z: 634 (M+,
1%). Calculated for C32H30N2O10S (634.65): C, 60.56;
H, 4.76; N, 4.41. Found: C, 60.44; H, 4.82; N, 4.60. IR
(KBr): ν 1752 (C¼O), 1699 (C¼O) cmꢀ1
.
1H-NMR
(500 MHz, CDCl3): δ = 1.95 (3H, s, Ac), 2.06 (3H, s,
Ac), 2.12 (3H, s, Ac), 2.21 (3H, s, Ac), 4.16–4.27 (3H,
m, H-5′, H-6′, H-6″), 5.26 (1H, dd, J = 3.00, 12.00 Hz,
2aryl, C-6aryl), 131.32 (C-9a), 136.95 (C-5a), 142.65 (C-
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. I. Khodair, M. A. Elsafi, and S. A. Al-Issa
Vol 000
H-4′), 5.30 (1H, t, J = 9.00 Hz, H-2′), 5.50 (1H, t,
J = 9.00 Hz, H-3′), 5.94 (1H, d, J1′,2′ = 10.50 Hz, H-1′),
Ph), 130.82 (C-5), 132.00 (C-9a), 136.49 (C1-Ph), 137.91
(C-5a), 143.51 (C-10), 154.83 (C-2), 163.38 (C-4).
2
7.29 (2H, m, H-2Ph, H-6Ph), 7.57 (4H, m, H-3Ph, H-4Ph,
H-5Ph, 8-H), 7.76 (1H, t, J = 7.50 Hz, H-7), 8.02 (1H, d,
J = 8.50 Hz, H-9), 8.07 (1H, d, J = 8.5 Hz, H-6), 8.13
(1H, s, H-10), 8.90 (1H, s, H-5). 13C-NMR (500 MHz,
CDCl3): δ = 20.62, 20.68 (4Ac), 61.54 (C-6′), 66.26 (C-
2′), 67.42 (C-3′), 72.23 (C-4′), 75.11 (C-5′), 82.96 (C-
1′), 119.23 (C-4a), 123.89 (C-9), 126.29 (C-7), 127.82
(C-8), 128.87 (C4-Ph), 129.07 (C-6), 129.14 (C-10),
129.56 (C3-Ph), 129.61 (C5-Ph), 129.66 (C2-Ph), 129.77
(C6-Ph), 130.41 (C-5), 131.34 (C-9a), 135.19 (C1-Ph),
136.98 (C-5a), 142.62 (C-10), 152.85 (C-2), 162.05 (C-
4), 169.42, 170.05, 170.23, 170.48 (4Ac).
CONCLUSIONS
In the present study, we have carried out the
successful synthesis of hitherto unreported 3-substituted
2-thioxo-2,3-dihydro-1H-benzo[g]quinazolin-4-ones 4a–
e, 3-substituted-2-alkylsulfanyl-2,3-dihydro-1H-benzo[g]
quinazolin-4-ones 5a–o, 3-substituted 2-(2′,3′,4′,6′-tetra-
O-acetyl-β-D-glucopyranosylsulfanyl)-2,3-dihydro-1H-be-
nzo[g]quinazolin-4-ones 8a–h, and 3-substituted 2-(β-D-
glucopyranosylsulfanyl)-2,3-dihydro-1H-benzo[g]quinaz-
olin-4-ones 9a,b. The conformational analyses of their
most stable configurations were established by NMR
spectroscopy.
3-Substituted-2-(β-D-glucopyranosylsulfanyl)-2,3-dihydro-
1H-benzo[g]quinazolin-4-ones (9a,b).
The protected
nucleosides 8b,d (1 mmol) was stirred in saturated NH3/
MeOH (5%, 50 mL) at room temperature for 12 h until
the starting material was consumed (TLC, ether
petroleum ether, 90:10). The solvent was removed in
vacuo, and the residue was chromatographed on silica gel
with a gradient at 1–5% MeOH in CH2Cl2 to afford the
deprotected nucleosides 9a,b as a white solid.
Acknowledgments. Research Centre (King Saud University) is
thanked for carrying out the measurement of IR, H-NMR, 13C-
1
NMR, and MS. Ahmed I. Khodair is grateful for an Alexander
von Humboldt-Fellowship (Alexander von Humboldt-Stiftung).
3-Ethyl-2-(β-D-glucopyranosylsulfanyl)-2,3-dihydro-1H-ben
zo[g]quinazolin-4-one (9a). Yield: 0.14 g (33%), mp: 308–
REFERENCES AND NOTES
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C20H22N2O6S (418.46): C, 57.40; H, 5.30; N, 6.69.
Found: C, 57.39; H, 5.41; N, 6.53. IR (KBr): ν 3406
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1
(OH), 1686 (C¼O) cmꢀ1. H-NMR (500 MHz, CD3OD):
δ = 1.38 (3H, t, J = 7.05 Hz, N3-CH2CH3), 3.46 (2H, m,
H-3′, H-4′), 3.54 (2H, m, H-5′, H-6′), 3.71 (1H, dd,
J = 5.10, 12.02 Hz, H-6″), 3.85 (1H, dd, J = 2.00,
10.50 Hz, H-2′), 4.22 (2H, q, J = 7.05 Hz, N3-CH2CH3),
2
5.81 (1H, d, J1′,2′ = 10.50 Hz, H-1′), 7.46 (1H, d,
J = 7.50 Hz, H-8), 7.59 (1H, t, J = 7.50 Hz, H-7), 7.98
(1H, d, J = 8.50 Hz, H-9), 8.02 (1H, d, J = 8.5 Hz, H-6),
8.04 (1H, s, H-10), 8.74 (1H, s, H-5).
3-Phenyl-2-(β-D-glucopyranosylsulfanyl)-2,3-dihydro-1H-b
enzo[g]quinazolin-4-one (9b).
Yield: 0.18 g (38%), mp:
296–298°C (dec.). MS: m/z: 466 (M+, 3%). Calculated
for C24H22N2O6S (466.51): C, 61.79; H, 4.75; N, 6.00.
Found: C, 61.86; H, 5.02; N, 5.88. IR (KBr): ν 3408
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1
(OH), 1682 (C¼O) cmꢀ1. H-NMR (500 MHz, CD3OD):
δ = 3.40 (2H, m, H-3′, H-4′), 3.58 (2H, M, H-5′, H-6′),
3.74 (1H, dd, J = 5.10, 12.02 Hz, H-6″), 3.87 (1H, dd,
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2
J = 2.00, 10.50 Hz, H-2′), 5.70 (1H, d, J1′,2′ = 10.50 Hz,
H-1′), 7.37 (2H, d, J = 3.20 Hz, H-2Ph, H-6Ph), 7.47–7.61
(5H, m, H-3Ph, H-4Ph, H-5Ph, H-7, H-8), 7.96 (2H, t,
J = 9.25 Hz, H-6, H-9), 8.03 (1H, s, H-10), 8.71 (1H, s,
H-5). 13C-NMR (500 MHz, CD3OD): δ = 62.31 (C-6′),
70.69 (C-4′), 72.52 (C-2′), 79.50 (C-5′), 81.84 (C-3′),
85.74 (C-1′), 119.08 (C-4a), 124.58 (C-9), 126.77 (C-7),
126.91 (C-8), 128.86 (C4-Ph), 128.51 (C-6), 129.21 (C-
10), 129.49 (C3-Ph), 130.03 (C5-Ph), 130.32 (C2-Ph, C6-
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Simple and Efficient Synthesis of Novel 3-Substituted 2-Thioxo-2,3-dihydro-1H-
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