The synthesis of some new quinazolone derivatives of potential biological activity

Article abstract of DOI:10.1080/10426500500543834

The refluxing of 3-amino-6,8-dibromo-2-thioxo-2,3-dihydro-1H-quinazolin-4- one (5) with ethyl chloroformate and/or ethyl chloroacetate afforded compounds 6 and 7 . The reaction of 5 with ethyl bromobutyrate, chloroacetyl chloride, phenacyl chloride, and p

Full text of DOI:10.1080/10426500500543834

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Phosphorus, Sulfur, and Silicon
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The Synthesis of Some New
Quinazolone Derivatives of
Potential Biological Activity
A. A. El-Barbary a , A. Z. Abou El-Ezz a , A. M. Sharaf
a & C. Nielsen b
a Chemistry Department , Tanta University , Tanta,
Egypt
b Retrovirus Laboratory, Department of Virology ,
State Serum Institute , Copenhagen, Denmark
Published online: 01 Feb 2007.
To cite this article: A. A. El-Barbary , A. Z. Abou El-Ezz , A. M. Sharaf & C. Nielsen
(2006) The Synthesis of Some New Quinazolone Derivatives of Potential Biological
Activity, Phosphorus, Sulfur, and Silicon and the Related Elements, 181:8, 1895-1912,
DOI: 10.1080/10426500500543834
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Phosphorus, Sulfur, and Silicon, 181:1895–1912, 2006
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500500543834
The Synthesis of Some New Quinazolone Derivatives
of Potential Biological Activity
A. A. El-Barbary
A. Z. Abou El-Ezz
A. M. Sharaf
Chemistry Department, Tanta University, Tanta, Egypt
C. Nielsen
Retrovirus Laboratory, Department of Virology, State Serum Institute,
Copenhagen, Denmark
The refluxing of 3-amino-6,8-dibromo-2-thioxo-2,3-dihydro-1H-quinazolin-4-one
(5) with ethyl chloroformate and/or ethyl chloroacetate afforded compounds 6
and 7. The reaction of 5 with ethyl bromobutyrate, chloroacetyl chloride, phenacyl
chloride, and phenyl isocyanate yielded compounds 8, 9, 11, and 12. The coupling
of 5 with (2,3,4,6-tetra-O-acetyl-α-D-gluopyranosyl)bromide(ABG) in DMF at r.t.
gave 3-amino-6,8-dibromo-2-(2ꢀ,3ꢀ,4ꢀ,6ꢀ-tetra-O-acetyl-β-D-glucopyranosyl)thioxo-
2,3-dihydro-1H-quinazolin-4-one (14). The deblocking of 14 in sodium methoxide
gave 5. 3-Amino-6,8-dibromo-2-methylthio-3H-quinazolin-4-one (16) was prepared
by stirring 5 with methyl iodide in methanol. The treatment of 16 with hydrazine
hydrate afforded 4. The condensation of 4 with aldehydes furnished 3,5-dibromo-
2-arylaminobenzoic acid hydrazide (18a–c). The refluxing of 18a with acetic anhy-
dride gave 3-(benzylideneamino)-6,8-dibromo-2-methyl-3H-quinazolin-4-one (19).
Hydrazones 20a–f were prepared by the condensation of 4 with pentoses and/or
hexoses. The acetylation of (20a–f) with acetic anhydride gave the acetyl deriva-
tives 21a–f.
Keywords Aldopentoses and hexoses; aminoquinazolenes; HIV; hydrazides; microbial
activity
Received September 5, 2005; accepted October 20, 2005.
The authors are thankful to the Danish International Development Agency (DANIDA)
for their support. Thanks are also due to Dr. Ahmed I. Mowaad, Biochemistry Depart-
ment, Faculty of Agriculture, El-Fayoum, El-Fayoum Branch, Cairo University, Egypt,
for testing antimicrobial activity.
Address correspondence to A.A. El-Barbary, Tanta University, Chemistry Department,
Faculty of Science, Tanta. Egypt. E-mail: aaelbarbary@hotmail.com
1895

1896
A. A. El-Barbary et al.
INTRODUCTION
3H-quinazolin-4-one and their derivatives have been reported to
possess significant activity as antihypertensive,1 antifibrillatory,
choleretic, antiphlogistic,2 antimitotic anticancer,3 antifungal,4,5 and
anticonvulsant agents.6 Quinazolinones were reported to possess di-
verse pharmacological activities such as a CNS depressant,7 hypnotic,
antiinflamatory,8 antitumor,9 muscle relaxants,10 and antineoplastic
activity.11 These results prompted us to continue our earlier work of
synthesizing some other new derivatives for evaluating their biological
antimicrobial activity as anti–HIV, anti–HBV, and schistosomiasis.
RESULTS AND DISCUSSION
The bromination of 2-aminobenzoic acid (1) with bromine in glacial
acetic acid at r.t. gave 2-amino-3,5-dibromobenzoic acid (2), which was
esterified by refluxing in a mixture of ethanol and sulfuric acid to af-
ford 3,12 which, on treatment with hydrazine hydrate in ethanol, fur-
nished 2-amino-3,5-dibromo benzoic acid hydrazide (4).13 The cycliza-
tion of 4 with carbon disulfide in boiling ethanol afforded the new com-
pound 3-amino-6,8-dibromo-2-thioxo-2,3-dihydro-1H-quinazolin-4-one
(5) (Scheme 1). A similar structure of 5 was prepared through the re-
action of isatoic anhydride with thioamide to afford 2-substituted-4(3H)
quinazolinones.14
The IR spectrum of 5 showed the existence of NH at 2814 cm−1. Its
1H NMR spectrum showed the presence of a singlet at 6.55 ppm (2H,
NH2) and a broad signal at 14.61 ppm (1H, NH). Its 13C NMR spec-
trum showed the existence of C N at 158.84 ppm and C O at 176.08
ppm. The mass spectrum of 5 containing bromine atoms showed frag-
ments corresponding to the typical bromine isotope 79Br and 81Br pat-
terns. Thus, the mass spectrum showed its M+1 and M+2 peaks at m/z
351 (93%, C8H5Br2N3OS) and 278 (100%, C7H4Br2NO), respectively
(Scheme 1).
The fusion of 5 with either ethyl chloroformate or ethyl chloroac-
etate yielded thiocarbonic acid S-(3-amino-6,8-dibromo-4-oxo-3,4-
dihydroquinazolin-2-yl)ester-O-ethyl ester (6) and/or (3-amino-6,8-
dibromo-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetic acid ethyl
ester (7), respectively. The reaction of 5 with ethyl 2-bromobutyrate
in sodium ethoxide at r.t. afforded 2-(3-amino-6,8-dibromo-3,4-
dihydroquinazolin-2-ylsulfanyl)butyric acid ethyl ester (8). The struc-
tures of 6–8 were suggested by different spectroscopic data (IR,1H,
13C NMR, and MS). Their IR spectra showed the existence of the C O
1
(ester) in the range 1735–1765 cm−1. Their H NMR spectra showed

The Synthesis of Some New Quinazolone Derivatives
1897
SCHEME 1
the appearance of a triplet (3H, CH3) in the range of 1.20–1.54, and a
quartet (2H, CH2) in the range 4.14–4.65 ppm. The 13C NMR spectra
of compounds 6–8 showed the existence of the C O (ester) in the range
of 145.54–163.66 ppm. The mass spectrum of 7 showed m/z 435 (M+,
71 %).
The stirring of 5 with chloroacetyl chloride in dioxane at 25◦C or at
boiling temperature in the presence of triethylamine yielded 3-amino-
6,8-dibromo-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)acetyl chloride
(9) and not the desired cyclic compound 6,8-dibromo-3,4-dihydro-1-thia-
4,4a,9-triazaanthracene-2,10-dione (10). The IR pectrum of 9 showed
the (COCH2Cl) at 1718 cm−1. Its 1H NMR spectrum showed a singlet at
4.27 ppm (2H, CH2) and a singlet at 6.89 ppm (2H, NH2). Its 13C NMR
spectrum showed the existence of a (CH2) signal at 34.14 ppm; (Carom.)
signals at 105.78, 106.65, 109.91, 128.99, 136.96, and 143.18 ppm;
a (C N) signal at 162.55 ppm; a (cyclic, C O) at 163.36 ppm; and a
(COCH2Cl) at 168.89 ppm. The stirring of 5 with phenacyl chloride at
25◦C in anhydrous DMF and anhydrous potassium carbonate afforded
3-amino-6,8-dibromo-2-(2-oxo-2-phenylethylsulfanyl)-3H-quinazol-in-
4-one (11). The IR spectrum of 11 showed (COPh) at 1728 cm−1. Its 1H
NMR spectrum showed a singlet at 5.35 ppm (2H, CH2CO), a broad sin-
glet at 6.62 (2H, NH2), and a multiplet at 7.65-7.82 ppm (5H, C6H5). The
13C NMR spectrum of 11 showed the CH2 signal at 40.39 ppm, (C N)
at 162.57 ppm, (C O, cyclic) at 163.36 ppm, and (COPh) at 192.65 ppm.
The treatment of 5 with phenyl isocyanate in anhydrous pyri-
dine either at r.t. or by reflux yielded 5,7-dibromo-3-phenyl-3H-
[1,2,4]triazolo[5,1-b]quinazoline-2,9-dione (12) as the sole product
(TLC) and not the open structure (13). The IR spectrum of 12 showed

1898
A. A. El-Barbary et al.
1
the C O at 1598 cm−1 and (C O, cyclic) at 1645 cm−1. Its H NMR
spectrum showed a multiplet at 6.43–7.04 ppm (5H, Harom), and a sin-
glet (1H, NH) at 11.02 ppm. Its 13C NMR spectrum showed a C N at
163.72 ppm and a C ONH at 171.23 ppm (Scheme 2).
SCHEME 2
The coupling of
5
with (2,3,4,6-tetra-O-acetyl-α-D-glucopy-
ranosyl)bromide (ABG) in DMF at r.t. yielded 3-amino-6,8-dibromo-
2(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)thioxo-2,3-dihydro-1H-
quinazolin-4-one (14). Its IR spectrum showed a sharp band at
1748 cm−1 (C O, acetyl). The 1H NMR spectrum showed the presence
of 4 characteristic signals due to four acetyl groups CH3CO (s) of the
sugar moiety in the range 1.95–2.12 ppm and the anomeric proton in
the range 4.95–5.96 ppm. Its 13C NMR spectrum showed 4 signals (4
CH3) in the range 20.14–20.23 and 4 signals (4 C O, acetyl) in the
range 169.21–169.73 ppm. The mass spectrum of compound 14 showed
m/z 681 (M +, C22H23Br2N3O10S, 75%).
The deblocking of 14 using sodium methoxide at r.t. yielded
the starting aglycone15 and not the desired deblocked compound
6,8-dibromo-2-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-
ylsulfanyl)-3H-quinazolin-4-one (15) (Scheme 3). 3-amino-6,8-dibromo-
2-methylthio-3H-quinazolin-4-one (16) can be synthesized by stirring 5
with methyl iodide in methanol at 25◦C. The IR spectrum of 16 showed

The Synthesis of Some New Quinazolone Derivatives
1899
SCHEME 3
1
the NH2 sym at 3338 cm−1 and 3453 cm−1 due to (NH2 antisym). Its H
NMR spectrum showed the appearance of s, 3H, and CH3 at 2.80 ppm
and s, 2H, and NH2 at 6.89 ppm. Its 13C NMR spectrum showed
CH3 at 14.19 ppm. The mass spectrum of 16 showed m/z at 365 (M+,
98 %). The refluxing of 16 with hydrazine hydrate in ethanol furnished
2-amino-3,5-dibromobenzoic acid hydrazide (4) instead of the expected
3-amino-6,8-dibromo-2-hydrazino-3H-quinazolin-4-one (17).
The boiling 4 with some aromatic aldehydes, namely benzaldehyde,
4-methoxybenzaldehyde, and 2-nitrobenzaldehyde in ethanol, afforded
the corresponding Schiff bases 3,5-dibromo-2-arylamino benzoic acid
hydrazide (18a–c) (Scheme 4). IR spectra of compounds 18a–c showed
C N bands in the range 2849–2928 cm−1, NH in the range 3185–
1
3250 cm−1, and NH2 in the range 3339–3362 cm−1. H NMR spectra
showed a signal (1H, CH) in the range 8.12–8.40 ppm. 13C NMR spectra
showed C N signals at 152.13–156.61 ppm. The refluxing of 18a with
acetic anhydride gave 3-(benzylideneamino)-6,8-dibromo-2-methyl-3H-
quinazolin-4-one (19). For the formation of 19, it is supposed that the
acetylation of the NH2 group of 18a took place followed by an internal
nucleophilic attack and the elimination of H2O. Its 1H NMR spectrum
showed a CH3 as a singlet (3H) at 2.45 ppm. Its 13C NMR spectrum
showed a CH3 signal at 20.77 ppm.
The sugar hydrazones 20a–f were prepared by the refluxing of 4 with
an equimolar amounts of L-arabinose, D-ribose, D-xylose, D-glucose,
D-galactose, and D-mannose in an aqueous ethanolic solution in the
presence of a catalytic amount of acetic acid. IR spectra of 20a–f showed
NH band in the range 3188–3210 cm−1 and a broad band of OH in the

1900
A. A. El-Barbary et al.
SCHEME 4
1
range 3421–3476 cm−1. H NMR spectra of these hydrazones showed
signals (1H, CH N) in the range 7.10–7.79 ppm. The structures of com-
pounds 20a–f were also confirmed by the 13C NMR data. For example,
the 13C NMR spectrum of 20e was characterized by the presence of sig-
nals at 63.02, 66.02, 68.17, 68.90, and 69.68 ppm (C-6ꢀ, C-5ꢀ, C-4ꢀ, C-3ꢀ,
and C-2ꢀ) of the galactose moiety and CH N at 154.86 ppm.
The acetylation of the aldehydo sugar hydrazones (20a–f) with
acetic anhydride in pyridine at r.t. gave the corresponding per-O-
acetylaldehydosugar[1-acetyl-1-(N-acetylamino-2-amino-3,5-dibromo-
benzoyl]hydrazones (21a–f) (Scheme 5). IR spectra of 21a–f showed
C N at 1615–1618 cm−1, a N C O (acetyl) at 1695–1699 cm−1, and an
O-acetyl at 1751–1756 cm−1. The structures of compounds 21a–f were
further confirmed by 1H NMR and 13C NMR data (see the experimental
section).
BIOLOGICAL ACTIVITY
All compounds were tested against HIV-1. The test was performed in
MT4 cell cultures infected with wild type HIV-1 (strain IIIB) using
the assay as previously described.16 The compounds were inactive at
100 uM or inactive at subtoxic concentrations. None of the tested com-
pounds showed any significant antiviral activity at 100 µM against
HIV-1.
In addition, the new products were tested as Accaros: Spider mite
(Tetranychus-urticae), (Koch), fungicides (Rhizoctonia solani, Fusarium
oxysporium, Fusarium solani, Verticillium dahliae, and Verticillium

The Synthesis of Some New Quinazolone Derivatives
1901
SCHEME 5
sulphurellium), and bactericides (Psedomonas solani- serum, Erwinia
carotovora, and Ralstonia salanceanum) at a concentration of 10–100
ppm. None of them showed any activity.
EXPERIMENTAL
All melting points were uncorrected and performed in an open capillary
melting point apparatus. Microanalyses were performed by Microanal-
ysis Unit, Faculty of Science, Cairo University, Egypt and Microanaly-
sis Unit, Central Laboratory, Tanta University, Egypt. IR spectra were
recorded with a Perkin-Elmer 1720 spectrometer. NMR spectra were
recorded on a Bruker AC 250 FT NMR spectrometer at 250 MHz for
1H and 62.9 MHz for 13C, on a Varian UNITY 500 NMR spectrometer
1
at 500 MHz for H or 125.7 MHz for 13C, and on a Bruker 200 MHz
and Bruker 90 MHz spectrometer using TMS as an internal standard
DMSO as a solvent. Chemical shifts (δ) are reported in parts per million
(ppm), and signals are expressed as s (singlet), d (doublet), t (triplet),
q (quartet), m (multiplet) or br (broad). Mass spectra were recorded
using electron ionization on a Varian Mat 311A spectrometer and us-
ing fast atom bombardment on a kratos MS 50 spectrometer. Silica gel

1902
A. A. El-Barbary et al.
(0.040–0.063 mm) was used for the column chromatography and was
purchased from Merck.
The Synthesis of 3-Amino-6,8-dibromo-2-thioxo-2,3-dihydro-
1H-quinazolin-4-one (5)
A mixture of compound 4 (10 g, 0.03 mol),13 sodium hydroxide (1.2 g,
0.03 mol), and carbon disulphide (0.7 mL, 0.03 mol) in ethanol (120 mL)
was refluxed for 15 h (TLC). The solvent was distilled off under reduced
pressure, and water was added to the residue (50 mL). The precipi-
tate was filtered off, washed with cold water (100 mL), and neutral-
ized with dil. HCl (1:1). The formed precipitate was filtered off, washed
with water (100 mL), and recrystallized from ethanol to afford com-
pound 5. Yield 5 g (51%); m.p. 260–262◦C; IR (KBr) υ = 1610 (C O),
3263 (NH2, sym.), 3317 (NH2, antisym.) cm−1 1H NMR (DMSO-d6)
;
δ = 6.55 (s, 2H, NH2), 7.68 (s, 1H, H-7), 7.70 (s, 1H, H-5), 14.52 (s, 1H,
NH); 13C NMR (DMSO-d6) δ = 105.87, 106.38, 110.01, 128.73, 137.08,
142.82 (Carom.), 158.54 (C O), 176.08 (CS) ppm; MS (EI) m/z= 349 (M+,
C8H5Br2N3OS, 45%), (79Br, 79Br)], 350 [12%, (79Br, 80Br; 80Br, 79Br)],
351 [92%, M+C12H11Br2N3O3S (80Br, 80Br; 79Br, 81Br; 81Br, 79Br)], 352
[13%,(80Br, 81Br; 81Br, 80Br)], 353 [46%, (81Br, 81Br)]. 278 (M+ beak
100%). Anal. calcd. for C8H5Br2N3OS: C, 27.37; H, 1.44; N, 11.97. Found:
C, 27.09; H, 1.23; N, 12.00.
The Reaction of Compound 5 with Ethyl Chloroformate
and/or Ethyl Chloroacetate
Compound 5 (1 g, 0.02 mol) was fused in ethyl chloroformate and/or
ethyl chloroacetate for 4 h (TLC). The excess of the reagent was evapo-
rated to dryness under vaccum. The solid residue was crystallized from
petroleum ether (80–100◦C) to give compounds 6 and 7, respectively.
Thiocarbonic Acid S-(3-amino-6,8-dibromo-4-oxo-3,4-dihydro-
quinazolin-2-yl) Ester O-ethyl Ester (6)
Yield 1 g (87%); m.p. 190–192◦C; IR (KBr) υ = 1626 (cyclic, C O), 1765
1
(COO), 2987 (CH), 3356 (NH2, sym), 3459 (NH2, antisym) cm−1; H
NMR (DMSO-d6) δ = 1.54 (t, 3H, CH3), 4.65 (q, 2H, CH2), 6.11 (s, 2H,
NH2), 7.75 (s, 1H, H-7), 7.87 (s, 1H, H-5); 13C NMR (CDCl3) δ = 14.11
(CH3), 65.68 (CH2), 129.88 (C N), 138.83 (cyclic, C O), 143.07 (COO),
162.21 (NCN) ppm. Anal. calcd. for C11H9Br2N3O3S: C, 31.23; H, 2.14;
N, 9.93. Found: C, 31.30; H, 2.04; N, 9.89.

The Synthesis of Some New Quinazolone Derivatives
1903
(3-Amino-6,8-dibromo-4-oxo-3,4-dihydroquinazolin-2-ylsulfan-
yl)acetic Acid Ethyl Ester (7)
Yield 1.2 g (89%); m.p. 120–122◦C; IR (KBr) υ =1615 (C O), 1730
1
(COO), 2924 (CH), 3329 (NH2, sym), 3452 (NH2, antisym) cm−1; H
NMR (DMSO-d6) δ = 1.20 (t, 3H, CH3), 4.21 (q, 2H, CH2), 4.36 (s, 2H,
SCH2), 6.86 (s, 2H, NH2), 7.80 (s, 1H, H-7), 7.84 (s, 1H, H-5); 13C NMR
(DMSO-d6) δ = 13.91 (CH3), 33.70 (CH2CH3), 61.55 (SCH2), 105.74,
106.56, 109.91, 128.95, 136.96, 143.17 (Carom.), 162.21 (C N), 163.42
(C O), 167.66 (COO) ppm; MS (EI) m/z= 435 [M+C12H11Br2N3O3S,
71%, (79Br, 79Br)], 436 [14%, (79Br, 80Br; 80Br, 79Br)], 437 [100%, (80Br,
80Br; 79Br, 81Br; 81Br, 79Br)], 438 [23%, (80Br, 81Br; 81Br, 80Br)], 439 [70%,
(81Br, 81Br)]. Anal. calcd. for C12H11Br2N3O3S: C, 32.97; H, 2.54; N, 9.61.
Found: C, 32.92; H, 2.34; N, 9.70.
2-(3-Amino-6,8-dibromo-3,4-dihydroquinazolin-2-ylsulfanyl)-
butyric Acid Ethyl Ester (8)
Compound 5 (1.5 g, 0.004 mol) was dissolved in sodium ethoxide (0.2 g of
Na in 20 mL of absolute ethanol), and ethyl 2-bromobutyrate (2 mL) was
added. The reaction mixture was stirred at r.t. for 10 h (TLC). The solid
product was filtered off, washed with dis. water (50 mL), recrystallized
from methanol, filtered, and dried to afford 8. Yield 1.1 g (93%); m.p.
120–122◦C; IR (KBr) υ = 1617 (C O), 1742 (COO), 2937 (CH), 3359
(NH2, sym), 3430 (NH2, antisym) cm−1; 1H NMR (DMSO-d6) δ = 1.26 (t,
3H, CH CH2CH), 1.332 (t, 3H, CH3CH2O), 4.16 (m, 2H, CH CH), 4.27
3
2
(q, 2H, OCH CH3), 6.319 (s, 2H, NH2), 7.69 (s, 1H, H-7), 7.72 (s, 1H, H-5);
2
13C NMR (DMSO-d6) δ = 13.90 (CH3CH2CH), 14.76 (CH3CH2O), 64.16
(CH2CH), 84.92 (CH3CH2O), 105 (CH), 109.77, 118.55, 129.93, 135.75
and 144.82 (Carom) ppm; MS (EI) m/z= 466 (M+1 C14H15Br2N3O3S, 5%),
278 (C7H4Br2NO, 100%); Anal. calcd. for C14H15Br2N3O3S: C, 36.15; H,
11.25; N, 9.03. Found: C, 36.01; H, 11.37; N, 8.89.
3-Amino-6,8-dibromo-4-oxo-3,4-dihydroquinazolin-2-ylsulfan-
yl)acetyl Chloride (9)
To a solution of compound 5 (1.5 g, 0.004 mol) in dioxane (15 mL) was
added chloroacetyl chloride (0.3 mL, 0.004 mol), followed by the addi-
tion of few drops of triethylamine. The reaction mixture was stirred at
5◦C for 5 h (TLC). The solid product that formed was filtered off, recrys-
tallized from petroleum ether (80–100◦C), and dried to give 9. Yield
1.6 g (94%); m.p. 170–172◦C; IR (KBr) υ = 1614 (cyclic, C O), 1718
1
(COCl), 2924 (CH), 3464 (NH2) cm−1; H NMR (DMSO-d6) δ = 4.27 (s,

1904
A. A. El-Barbary et al.
2H, CH2), 6.89 (s, 2H, NH2), 7.84 (s, 1H, H-7), 7.87 (s, 1H, H-5); 13C NMR
(DMSO-d6) δ = 34.14 (CH2), 105.78, 106.65, 109.91, 128.99, 136.96,
143.18 (Carom), 162.55 (C N), 163.36 (cyclic, C O), 168.89 (COCl) ppm.
Anal. calcd. for C10H6Br2ClN3O2S: C, 28.10; H, 1.41; N, 9.83. Found: C,
28.50; H, 1.60; N, 9.68.
3-Amino-6,8-dibromo-2-(2-oxo-2-phenylethylsulfanyl)-
3H-quinazolin-4-one (11)
To a solution of compound 5 (2.3 g, 0.006 mol) in anhydrous dimethyl-
formamide (15 mL) was added anhydrous potassium carbonate (0.8 g,
0.006 mol) followed by the addition of phenacyl chloride (0.9 g, 0.006
mol). The reaction mixture was stirred at r.t. for 8 h (TLC). The solid
product that formed was filtered off and recrystallized from methanol
to afford 11. Yield 1.8 g (64%); m.p. 200–202◦C; IR (KBr) υ = 1613
(cyclic, C O), 1728 (C O C6H5), 3338 (NH2, sym), 3460 (NH2, antisym)
cm−1; 1H NMR (DMSO-d6) δ = 5.35 (s, 2H, CH2CO), 6.62 (s, 2H, NH2),
7.65–7.82 (m, 5H, C6H5), 8.12 (s, 1H, H-7), 8.14 (s, 1H, H-5); 13C NMR
(DMSO-d6) δ = 40.39 (CH2), 105.75, 106.61, 109.89, 128.38, 128.83,
128.96,133.96, 134.92, 136.94 and 143.16 (Carom.), 162.57 (C N), 163.36
(cyclic, C O), 192.65 (COC6H5) ppm. Anal. calcd. for C6H11Br2N3O2S:
C, 40.96; H, 2.36; N, 8.96. Found: C, 40.90; H, 2.46; N, 8.77.
5,7-Dibromo-3-phenyl-3H-[1,2,4]triazolo[5,1-b]quinazoline-
2,9-dione (12)
To a solution of compound 5 (1g, 0.003 mol) in anhydrous pyridine
(25 mL) was added phenyl isocyanate (0.3 mL, 0.003 mol). The reac-
tion mixture was refluxed for 6 h (TLC). The solvent was evaporated
to dryness under vacuum, and the residual solid was crystallized from
methanol and dried to give 12. Yield 1.8 g (64%); m.p. 200–202◦C; IR
(KBr) υ = 1598 (CONH), 1645 (cyclic, C O), 2920 (CH), 3718 (NH2,
sym), 3838 (NH2, antisym) cm−1; 1H NMR (DMSO-d6)δ = 6.43–7.04 (m,
5H, Harom.), 7.80 (s, 1H, H-5), 8.01 (s, 1H, H-7), 10.42 (s, 1H, NH);
13C NMR (DMSO-d6) δ = 112.3, 129.4, 116.4 and 143.01 (Ph, Carom),
163.33(C N), 168.45 (cyclic, C O), 171.23 (CONH) ppm. Anal. calcd.
for C15H8Br2N4O2: C, 41.32; H, 1.85; N, 12.85. Found: C, 41.47; H, 1.79;
N, 12.77.
3-Amino-6,8-dibromo-2(2ꢀ,3ꢀ,4ꢀ,6ꢀ-tetra-O-acetyl-β-D-glucopy-
ranosyl)thioxo-2,3-dihydro-1H-quinazolin-4-one (14)
To a solution of compound 5 (1.5 g, 0.004 mol) in dimethylformamide
(10 mL) was added a few drops of triethylamine and ABG (1.6 g,

The Synthesis of Some New Quinazolone Derivatives
1905
0.004 mol). The reaction mixture was stirred at r.t. for 3 h (TLC). The
solvent was evaporated to dryness under vacuum. The solid residue was
poured onto cold water, and the solid formed was filtered off, washed
with cold water, dried, and recrystallized from ethanol to afford 14.
◦
Yield 0.7 g (26%); m.p. 170–172 C; IR (KBr) υ = 1617 (cyclic, C O),
1748 (C O, acetyl), 3385 (NH2, sym), 347 (NH2, antisym) cm−1; H
1
NMR (DMSO-d6) δ = 1.95–2.12 (s, 12H, 4CH3), 3.35 (s, 2H, Cꢀ6H2),
4.55-5.96 (H, sugar moiety), 6.92 (s, 2H, NH2), 7.85 (s, 1H, H-7), 7.92
(s, 1H, H-5); 13C NMR (DMSO-d6) δ = 20.14 (CH3, Cꢀ6), 20.19(CH3,
Cꢀ4), 20.23(CH3, Cꢀ2), 20.28 (CH3, Cꢀ3), 61.65, 67.65, 70.20, 72.47,
74.66, 81.01 (Cꢀ6,Cꢀ4,Cꢀ2, Cꢀ3, Cꢀ5, Cꢀ1anomeric,respectively), 105.81, 106.43,
109.61, 128.99, 137.30, 142.69 (Carom), 158.58 (C N), 163.98 (C O,
cyclic), 169.21, 169.46, 169.72, 169.73 (C O, acetyl) ppm; MS (EI)
m/z= 681 (M+, C22H23Br2N3O10S, 75%), 603 (100%); Anal. calcd. for
C23H23Br2N3O10S: C, 38.78; H, 3.40; N, 6.17. Found: C, 39.02; H, 3.52;
N, 6.49.
The Deblocking of 14
Compound 14 was dissolved in methanol (1.5 g, 0.01 mL), and two drops
of sodium methoxide solution (0.001 N) were added. The reaction mix-
ture was left at r.t. for 4 h (TLC). The solvent was evaporated under
vacuum, and the residual solid was dissolved in water neutralized with
dill. HCl. The solid formed was filtered off, washed with water, dried,
and recrystallized from ethanol to give the starting material 5. Yield
1.2 g (92%); m.p. 260–262◦C. M.p. and mixed m.p. of the product and
an authentic sample of 5 gave no depression.
3-Amino-6,8-dibromo-2-methylthio-3H-quinazolin-4-one (16)
Compound 5 (2 g, 0.0056 mol) was dissolved in methanol (20 mL) and
sodium hydroxide (0.3 g). Methyl iodide (0.03 mL, 0.0056 mol) was
added, and the reaction mixture was stirred at r.t. for 4 h (TLC). The
formed solid product was filtered off, recrystallized from methanol, fil-
tered, and dried to afford 16. Yield 3.5 g (58%); m.p. 178–180◦C; IR
(KBr) υ = 1619 (cyclic, C O), 2925 (CH), 3338 (NH2, sym), 3454 (NH2,
1
antisym) cm−1; H NMR (DMSO-d6) δ = 2.80 (s, 3H, CH3), 6.89 (s, 2H,
NH2), 7.82 (s, 1H, H-7), 7.85 (s, 1H, H-5); 13C NMR (DMSO-d6) δ = 14.19
(CH3), 105.73, 106.82, 109.85, 128.91, 136.81, 143.12 (Carom.), 163.26
(C N), 163.97 (cyclic, C O) ppm; MS (EI) m/z= 363 [C9H7Br2N3OS,
50%, (79Br, 79Br)], 364 [6.3%, (79Br, 80Br; 80Br, 79Br)], 365 [100%, (80Br,
80Br; 79Br, 81Br; 81Br, 79Br)], 366 [10%, (80Br, 81Br; 81Br, 80Br)], 367 [50%,

1906
A. A. El-Barbary et al.
(81Br, 81Br). Anal. calcd. for C9H7Br2N3OS: C, 29.61; H, 1.93; N, 11.51.
Found: C, 29.52; H, 2.00; N, 11.70.
2-Amino-3,5-dibromobenzoicaid Hydrazide (4)
A mixture of compound 16 (2 g, 0.01 mol) and hydrazine hydrate
(0.5 mL, 0.01 mol) in ethanol (20 mL) was refluxed for 4 h (TLC) and
then allowed to cool. The solid product was collected and recrystallized
from ethanol to afford 4. Yield 1.3 g (68%), m.p. 176–178◦C.13
The Synthesis of 3,5-Dibromo-2-aryl Aminobenzoic Acid
Hydrazide (18a–c)
A mixture of compound 4 (1.9 g, 0.01 mol) with the aromatic
aldehydes, namely benzaldehyde, 4-methoxybenzaldehyde, and 2-
nitrobenzaldehyde (0.01), in ethanol (20 mL) and few drops of glacial
acetic acid, was added. The reaction mixture was refluxed in ethanol
(20 mL) for 1–2.5 h (TLC). The solid product separated was filtered off
and recrystallized from ethanol to afford (18a–c), respectively.
2-Amino(benzylideneamino)-3,5-dibromobenzoic Acid
Hydrazide (18a)
Yield 1.1 g (83%); m.p. 218-220◦C; IR (KBr) υ = 1632 (C O), 2923 (CH),
3220 (NH), 3397 (NH2, sym), 3439 (NH2, antisym) cm−1 1H NMR
;
(DMSO-d6) δ = 6.55 (s, 2H, NH2), 7.46-7.80 (m, 5H, Harom.), 8.40 (s, 1H,
CH.), 11.86 (s, 1H, NH); 13C NMR (DMSO-d6) δ = 105.14 (CH), 127.04,
128.78, 130.12, 134.07, 136.81, 145.57 (Carom.), 152.14(C N), 168.17
(C O) ppm. Anal. calcd. for C14H11Br2N4O3: C, 42.35; H, 2.79; N, 10.58.
Found: C, 42.58; H, 2.76; N, 10.83.
3,5-Dibromo-2-amino[(4-methoxybenzylidene)amino]benzoic
Acid Hydrazide (18b)
Yield 1 g (71%); m.p. 210–212◦C; IR (KBr) υ = 1618 (C O, cyclic), 2928
(CH), 3225 (NH), 3362 (NH2, sym), 3498 (NH2, antisym) cm−1; 1H NMR
(DMSO-d6) δ = 3.73 (s, 3H, CH3), 6.46 (s, 2H, NH2), 6.81–7.84 (m, 5H,
Harom.), 8.13 (s, 1H, N CH.), 11.15 (s, 1H, NH); 13C NMR (DMSO-d6)
δ = 57.29 (OCH3), 126.98, 127.12, 128.33, 129.45, 130.61, 131.72, 132.01,
132.98 (Carom), 154.71 (C N), 164.32 (C O), 170.01 (C-OCH ) ppm.
3
Anal. calcd. for C15H13Br2N3O2: C, 42.18; H, 3.07; N, 9.84. Found: C,
42.34; H, 2.89; N, 9.70.

The Synthesis of Some New Quinazolone Derivatives
1907
3,5-Dibromo-2-amino[(2-nitrobenzylidene)amino]benzoic Acid
Hydrazide (18c)
Yield 1.7g (71%); m.p. 286–288◦C; IR (KBr) υ = 1654 (C O, cyclic), 2849
(CH), 3185 (NH), 3339 (NH2, sym), 3417 (NH2, antisym) cm−1; 1H NMR
(DMSO-d6)δ = 6.82 (s, 2H, NH2), 6.61–8.24 (m, 5H, Harom.), 8.12 (s, 1H,
N CH.), 11.32 (s, 1H, NH); 13C NMR (DMSO-d6) δ = 112.12, 115.42,
123.73, 124.51, 130.43, 139.72, 147.94, 148.01, (Carom.), 156.62 (C N),
166.53 (C O) ppm. Anal. calcd. for C14H10Br2N4O3: C, 38.04; H, 2.28;
N, 12.67. Found: C, 37.89; H, 2.40; N, 12.79.
3-(Benzylideneamino)-6,8-dibromo-2-methyl-3H-quinazolin-
4-one (19)
Compound 18a (1 g, 0.002 mol) was refluxed with acetic anhydride
(15 mL) for 4 h (TLC). The excess of solvent was evaporated un-
der vacuum to dryness. The solid product that formed was crystal-
lized from ethanol and dried to give 19. Yield 0.8 g (80%); m.p. 218–
220◦C; IR (KBr) υ = 1711 (C O, cyclic), 2922 (CH) cm−1
;
1H NMR
(DMSO-d6) δ = 2.45 (s, 3H, CH3), 7.45–7.60 (m, 6H, Harom + N CH),
8.33–8.45 (s, 2H, Harom); 13C NMR (DMSO-d6) δ = 20.77 (CH3), 67.36
(CH), 118.86–143.93 (Carom), 157.74 (C N), 166.01 (C O) ppm. Anal.
calcd. for C16H11Br2N3O: C, 45.64; H, 2.63; N, 9.98. Found: C, 45.46; H,
2.88; N, 8.36.
The Synthesis of Aldehydosugars (2-Amino-
3, 5-dibromobenzoyl) Hydrazones (20a–f)
A solution of the respective sugar pentoses and/or hexoses (0.01 mol)
in water (5 mL) was refluxed with a solution of (2-amino-3,5-
dibromobenzoyl)hydarzone (4) (2 g, 0.01 mol) in ethanol (20 mL) con-
taining 1 mL of glacial acetic acid for 5 h (TLC). The solid product
that separated on cooling was collected and recrystallized from ethanol/
water (1:1) to give (20a–f).
Aldehydo-L-arabinose(2-amino-3,5-dibromobenzoyl)hydra-
zone (20a)
Yield 2.5 g (87%); m.p. 204–206◦C; IR (KBr) υ = 1615 (C N), 1675
(C O), 3180 (NH), 3435 (OH) cm−1; 1H NMR (DMSO-d6) δ = 3.62–4.35
(m, 5H, arabinosyl protons), 6.01 (s, 2H, NH2), 7.5 (s, 1H, CH N-),
7.12–7.731 (m, 2H, Harom), 11.02 (s, 1H, NH); 13C NMR (DMSO-
d6) δ = 62.11, 65.83, 70.12, 74.03 (arabinosyl moiety), 109.82, 115.22,

1908
A. A. El-Barbary et al.
122.13, 133.76, 136.92, 145.19 (Carom), 159.20 (C N), 168.02 (C O)
ppm; MS (Maldi) m/z= 462 [48%, M+ + Na, (79Br, 79Br)], 464 [100%,
M+ + Na, (80Br, 80Br or 79Br, 81Br)], 466 [48%, M+ + Na, (81Br, 81Br)].
Anal. calcd. for C12H15Br2N3O5: C, 32.68; H, 3.43; N, 9.53. Found: C,
32.59; H, 3.38; N, 9.60.
Aldehydo-D-ribose(2-amino-3,5-dibromobenzoyl)hydrazone
(20b)
Yield 2.1g (75%); m.p. 210–212◦C; IR (KBr) υ = 1611 (C N), 1671
(C O), 3142 (NH), 3450 (OH) cm−1
;
1H NMR (DMSO-d6) δ = 3.51–
5.92 (m, 5H, ribosyl protons), 6.55 (s, 2H, NH2), 7.31–7.96 (m, 2H,
H
arom), 10.25 (s, 1H, NH); 13C NMR (DMSO-d6) δ = 62.12, 72.50,
73.41, 74.53 (carbon of ribosyl moiety), 115.42, 120.51, 126.12, 132.97,
138.53, 140.72 (Carom), 154.91 (C N), 166.02(C O) ppm. Anal. calcd. for
C12H15Br2N3O5: C, 32.68; H, 3.43; N, 9.53. Found: C, 32.60; H, 3.62; N,
9.27.
Aldehydo-D-xylose(2-amino-3,5-dibromobenzoyl)hydrazone
(20c)
Yield 2.6 g (92%); m.p. 198–200◦C; IR (KBr) υ = 1613 (C N), 1670
(C O), 3185 (NH), 3432 (OH) cm−1; 1H NMR (DMSO-d6) δ = 3.32–5.51
(m, 5H, xylosyl protons), 6.59 (s, 2H, NH2), 7.62–7.83 (m, 2H, Harom),
10.35 (s, 1H, NH); 13C NMR (DMSO-d6) δ = 62.39, 66.76, 69.70, 71.32,
76.50 (carbon of xylosyl moiety), 105.12, 110.06, 116.08, 130.07, 136.52,
145.25 (Carom), 165.92 (C O) ppm. Anal. calcd. for C12H15Br2N3O5: C,
32.68; H, 3.43; N, 9.53. Found: C, 32.82; H, 3.53; N, 9.05.
Aldehydo-D-glucose(2-amino-3,5-dibromobenzoyl)hydrazone
(20d)
Yield 2.5 g (85%); m.p. 210–212◦C; IR (KBr) υ = 1613 (C N), 1673
(C O), 3182 (NH), 3433 (OH) cm−1; 1H NMR (DMSO-d6) δ = 3.60–5.67
(m, 6H, glucosyl protons), 6.59 (s, 2H, NH2), 7.56–7.85 (m, 2H, Harom
and CH N), 10.60 (s, 1H, N H); 13C NMR (DMSO-d6) δ = 60.73, 71.46,
76.67, 77.87, 87.72, 90.89 (carbon of glucosyl moiety), 105.24, 110.03,
116.52, 129.69, 136.40, 145.06 (Carom), 157.42 (C N), 165.64 (C O) ppm.
Anal. calcd. for C13H17Br2N3O6: C, 33.14; H, 3.64; N, 8.92. Found: C,
33.30; H, 3.72; N, 9.00.

The Synthesis of Some New Quinazolone Derivatives
1909
Aldehydo-D-galactose(2-amino-3,5-dibromobenzoyl)hydra-
zone (20e)
Yield 2.8 g (89%) cm−1; m.p. 214–216◦C; IR (KBr) υ = 1618 (C N), 1679
1
(C O), 3188 (NH), 3421 (OH); H NMR (DMSO-d6) δ = 3.65–6.10 (m,
6H, galactosyl protons), 6.53 (s, 2H, NH2), 7.75–7.99 (m, 2H, Harom and
CH N), 11.66 (s, 1H, NHC O); 13C NMR (DMSO-d6) δ = 60.40, 66.02,
68.17, 68.90, 76.44 (C-6ꢀ, C-5ꢀ, C-4ꢀ, C-3ꢀ and C-2 carbon of galactosyl
moiety), 105.18, 110.01, 116.20, 130.17, 136.47, 145.35 (Carom), 154.86
(C N), 166.01 (C O) ppm; MS (Maldi) m/z= 492 [48%, M++ Na, (79Br,
79Br)], 494 [100%, M+ + Na, (80Br, 80Br or 79Br, 81Br)], 496 [48%, M++
Na, (81Br, 81Br)]. Anal. calcd. for C13H17Br2N3O6: C, 33.14; H, 3.64; N,
8.92. Found: C, 33.12; H, 3.56; N, 8.75.
Aldehydo-D-mannose(2-amino-3,5-dibromobenzoyl)hydra-
zone (20f)
Yield 1.3 g (46%) cm−1; m.p. 197–199◦C; IR (KBr) υ = 1642 (C N), 1674
(C O), 3110 (NH), 3476 (OH) cm−1; 1H NMR (DMSO-d6) δ = 3.54–5.62
(m, 6H, mannose protons), 6.54 (s, 2H, NH2), 7.15–7.97 (m, 2H, Harom
and CH N), 10.55 (s, 1H, NHC O); 13C NMR (DMSO-d6) δ =62.87,
64.10, 68.17, 68.97, 70.40 (C-6ꢀ, C-5ꢀ, C-4ꢀ, C-3ꢀ and C-2ꢀ (carbon of man-
nose moiety), 106.78, 107.38, 111.73, 130.51, 135.23, 143.41 (Carom),
157.61 (C N), 167.21(C O) ppm. Anal. calcd. for C13H17Br2N3O6: C,
33.14; H, 3.64; N, 8.92. Found: C, 32.99; H, 3.72; N, 9.03.
2ꢀ,3ꢀ,4ꢀ,5-Tetra-O-acetylaldehydo-L-arabinose[1-acetyl-1-(N-
acetylamino)-3,5-dibromobenzoyl]hydrazone (21a)
Yield 1.1 g (78%); m.p. 80–82◦C; IR (KBr) υ = 1645(C N), 1667 (C O,
cyclic), 1763 (C O), 2855 (CH), 3348 (NH2, sym), 3435 (NH2, anti-
sym) cm−1
;
1H NMR (DMSO-d6) δ = 1.89, 1.91, 1.94, 2.02, 2.05 (5s,
15H, 5CH3CO), 2.28 (s, 2H, CH2OAc), 5.28 (m, 1H, Cꢀ-5), 5.41 (d,
1H,J= 9.57 Hz, Cꢀ-4), 5.44 (d, 1H, J= 8.22 Hz, Cꢀ-3), 5.61 (m, 1H,
Cꢀ-2), 6.34 (m, 1H, Cꢀ-1), 6.57 (s, 2H, NH2), 7.15-7.97 (m, 2H, Harom);
13C NMR (DMSO-d6) δ = 20.38, 20.43, 20.50, 21.43 (4 OCH3CO), 22.20
(NCH3CO), 62.48, 67. 55, 68.55, 68.88, 87.55 (Cꢀ-5, Cꢀ-4, Cꢀ-3, Cꢀ-2,
Cꢀ-1), 106.51, 108.07, 109.61, 129.48, 138.07, 148.46 (Carom), 153.85
(C N), 169.05 (C O, base), 169.24, 169.40, 169.92 (4C O, acetyl),
170.01 (NCH3C O) ppm. Anal. Calcd. for C22H25Br2N3O10: C, 40.57;
H, 3.87; N, 6.45. Found: C, 40.72; H, 3.91; N, 6.60.

1910
A. A. El-Barbary et al.
2ꢀ,3ꢀ,4ꢀ,5-Tetra-O-acetylaldehydo-D-ribose[1-acetyl-1-(N-
acetylamino)-3,5-dibromobenzoyl]hydrazone (21b)
Yield 0.8 g (57%); m.p. 92–94◦C; IR (KBr) υ = 1657(C N), 1697 (C O,
cyclic), 1775 (C O), 2840 (CH), 3330 (NH2 sym), 3425 (NH2, anti-
sym) cm−1
;
1H NMR (DMSO-d6) δ = 1.75, 1.83, 1.98, 2.12, 2.20 (5s,
15H, 5CH3CO), 2.56 (s, 2H, CH2OAc), 5.11 (m, 1H, Cꢀ-5), 5.44 (d,
1H,J= 9.55 Hz, Cꢀ-4), 5.48 (d, 1H, J= 8.51 Hz, Cꢀ-3), 5.54 (m, 1H,
Cꢀ-2), 6.24 (m, 1H, Cꢀ-1), 6.35 (s, 2H, NH2), 7.41–7.95 (m, 2H, Harom);
13C NMR (DMSO-d6) δ = 20.23, 20.42, 20.53, 20.61 (4 OCH3CO), 21.75
(NCH3CO), 68.24, 68. 53, 71.46, 72.56, 78.42 (Cꢀ-5, Cꢀ-4, Cꢀ-3, Cꢀ-2, Cꢀ-
1), 110.16, 115.34, 119.49, 121.21, 138.47, 144.58 (Carom), 165.80 (C O,
cyclic), 169.52 (5C O) ppm. Anal. Calcd. for C22H25Br2N3O10: C, 40.57;
H, 3.87; N, 6.45. Found: C, 40.68; H, 4.16; N, 6.15.
2ꢀ,3ꢀ,4ꢀ,5-Tetra-O-acetylaldehydo-D-xylose [1-acetyl-1-(N-
acetylamino)-3,5-dibromobenzoyl]hydrazone (21c)
Yield 1 g (71%); m.p. 90–92◦C; IR (KBr): υ = 1668 (C N), 1686 (C O,
cyclic), 1779 (C O), 2886 (CH), 3335 (NH2, sym), 3421 (NH2, anti-
sym) cm−1
;
1H NMR (DMSO-d6) δ = 1.73, 1.89, 1.97, 2.15, 2.25 (5s,
15H, 5CH3CO), 2.59 (s, 2H, CH2OAc), 5.15 (m, 1H, Cꢀ-5), 5.65 (d,
1H,J= 9.52 Hz, Cꢀ-4), 5.45 (d, 1H, J= 8.50 Hz, Cꢀ-3), 5.50 (m, 1H,
Cꢀ-2), 6.30 (m, 1H, Cꢀ-1), 6.37 (s, 2H, NH2), 7.55–7.99 (m, 2H, Harom);
13C NMR (DMSO-d6) δ = 20.28, 20.40, 20.61, 20.65 (4 OCH3CO), 20.81
(NCH3CO), 63.22, 67.17, 68.02, 73.27, 80.13 (Cꢀ-5, Cꢀ-4, Cꢀ-3, Cꢀ-2, Cꢀ-1),
104.99, 110.05, 114.98, 128.22, 130.61, 137. 32 (Carom), 145.48 (C N),
166.59 (C O, cyclic), 169.03, 169.48 (4C O), 172.91(NCH3CO) ppm.
Anal. calcd. for C22H25Br2N3O10: C, 40.57; H, 3.87; N, 6.45. Found: C,
40.50; H, 3.80; N, 6.58.
2ꢀ,3ꢀ,4ꢀ,5ꢀ,6-Penta-O-acetylaldehydo-D-glucose[1-acetyl-1-(N-
acetylamino)-3,5-dibromobenzoyl]hydrazone (21d)
Yield 0.8 g (57%); m.p. 198–200◦C; IR (KBr) υ = 1671 (C N), 1695
(C O, cyclic), 1770 (C O), 2860 (CH), 3340 (NH2, sym), 3432 (NH2,
antisym) cm−1; 1H NMR (DMSO-d6) δ = 1.75, 1.90, 1.99, 2.20, 2.28, 2.51
(5s, 15H, 5CH3CO + NAc), 2.90 (s, 2H, CH2OAc), 5.11 (m, 1H, Cꢀ-5),
5.75 (d, 1H,J= 9.64 Hz, Cꢀ-4), 5.55 (d, 1H, J= 9.12 Hz, Cꢀ-3), 5.53 (m,
1H, Cꢀ-2), 6.35 (m, 1H, Cꢀ-1), 6.53 (s, 2H, NH2), 7.62–7.96 (m, 2H, Harom);
13C NMR (DMSO-d6) δ = 20.20, 20.33, 20.45, 20.52 (5 OCH3CO), 20.88
(NCH3CO), 62.06, 67. 48, 72.35, 73.54, 79.40, 79.43 (Cꢀ-6, Cꢀ-5, Cꢀ-4,
Cꢀ-3, Cꢀ-2, Cꢀ-1), 105.00, 110.08, 115.03, 130.69, 137.38, 145.46 (Carom),

The Synthesis of Some New Quinazolone Derivatives
1911
166.77 (C O, cyclic), 169.427, 169.44 (4C O), 172.73 (NCH3CO) ppm;
MS (Maldi) m/z= 722 [100%, M+−2, (79Br, 79Br)], 747 [15%, M+ +Na,
(80Br, 80Br or 79Br, 81Br). Anal. calcd. for C25H29Br2N3O12: C, 41.61; H,
4.04; N, 5.81. Found: C, 41.46; H, 3.78; N, 6.03.
2ꢀ,3ꢀ,4ꢀ,5ꢀ,6-Penta-O-acetylaldehydo-D-galactose[1-acetyl-1-(N-
acetylamino)-3,5-dibromobenzoyl]hydrazone (21e)
Yield 0.9 g (64%); m.p. 202–204◦C; IR (KBr) υ = 1682 (C N), 1676
(C O, cyclic), 1778 (C O), 2870 (CH), 3323 (NH2, sym), 3411 (NH2,
antisym) cm−1; 1H NMR (DMSO-d6) δ = 1.70, 1.85, 1.96, 2.10, 2.24, 2.95
(5s, 15H, 5CH3CO + NAc), 2.54 (s, 2H, CH2OAc), 5.13 (m, 1H, Cꢀ-5), 5.70
(d, 1H,J= 9.51 Hz, Cꢀ-4), 5.51 (d, 1H, J= 9.12 Hz, Cꢀ-3), 5.56 (m, 1H,
Cꢀ-2), 6.44 (m, 1H, Cꢀ-1), 6.68 (s, 2H, NH2), 7.80–8.20 (m, 2H, Harom);
13C NMR (DMSO-d6) δ = 19.99, 20.37, 20.59, 20.88 (4 OCH3CO), 21.23
(NCH3CO), 61.96, 67.10, 65.88, 68.19, 87.05, 89.24 (Cꢀ-6, Cꢀ-5, Cꢀ-4, Cꢀ-
3, Cꢀ-2, Cꢀ-1), 105.46, 106.84, 109.81, 128.89, 137.00, 143.34 (Carom),
164.46 (C O, cyclic), 169.92 (C O) ppm; MS (Maldi) m/z= 746 [100 %,
M+ Na, (79Br, 80Br)], 747 [59 %, M+ + Na, (80Br, 80Br or 79Br, 81Br)].
Anal. calcd. for C25H29Br2N3O12: C, 41.61; H, 4.04; N, 5.81. Found: C,
41.70; H, 4.00; N, 6.01.
2ꢀ,3ꢀ,4ꢀ,5ꢀ,6-Penta-O-acetylaldehydo-D-manose[1-acetyl-1-(N-
acetylamino)-3,5-dibromobenzoyl]hydrazone (21f)
Yield 1.1 g (78%); m.p. 182–184◦C; IR (KBr) υ = 1670 (C N), 1672
(C O, cyclic), 1776 (C O), 2884 (CH), 3320 (NH2, sym), 3418 (NH2,
antisym) cm−1
;
1H NMR (DMSO-d6) δ = 1.81, 1.84, 1.82, 2.15, 2.28,
2.92 (5s, 15H, 5CH3CO + NAc), 2.44 (s, 2H, CH2OAc), 5.10 (m, 1H,
Cꢀ-5), 5.69 (d, 1H,J= 9.55 Hz, Cꢀ-4), 5.59 (d, 1H, J= 9.12 Hz, Cꢀ-3),
5.61 (m, 1H, Cꢀ-2), 6.74(m, 1H, Cꢀ-1), 6.82 (s, 2H, NH2), 7.51-8.11
(m, 2H, Harom); 13C NMR (DMSO-d6) δ = 22.43, 22.35, 22.41, 23.01,
23.15 (5 OCH3CO), 24.18 (NCH3CO), 68.10, 68.35, 71.23, 75.41, 79.11,
79.93 (Cꢀ-6, Cꢀ-5, Cꢀ-4, Cꢀ-3, Cꢀ-2, Cꢀ-1), 117.10, 119.27, 134.35, 139.01,
141.74, 145.86 (Carom), 152.81 (C N), 165.12 (C O, cyclic), 170.50
(6C O) ppm; MS (Maldi) m/z= 746 [86%, M+ Na, (79Br, 80Br)],
747 [57 %, M++ Na, (80Br, 80Br or 79Br, 81Br)]. Anal. Calcd. for
C25H29Br2N3O12: C, 41.61; H, 4.04; N, 5.81. Found: C, 41.80; H, 3.90; N,
6.01.

1912
A. A. El-Barbary et al.
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