Hantzsch synthesis of bis(pyrido[2,3-d:6,5-d']dipyrimidines), bis(pyrimido[4,5-b]quinolines), and bis(benzo[4,5]imidazo[2,1-b]quinazolines) linked to pyrazole units as novel hybrid molecules

Article abstract of DOI:10.1080/00397911.2021.1913604

Bis(1-phenylpyrazole-4-carboxaldehydes) were utilized as versatile precursors to novel series of bis(pyrido[2,3-d:6,5-d']dipyrimidines), bis(pyrimido[4,5-b]quinolines), and bis(benzo[4,5]imidazo[2,1-b]quinazolines) derivatives which are linked to pyrazole

Full text of DOI:10.1080/00397911.2021.1913604

Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic
Chemistry
ISSN: (Print) (Online) Journal homepage: https://www.tandfonline.com/loi/lsyc20
Hantzsch synthesis of
bis(pyrido[2,3-d:6,5-d']dipyrimidines),
bis(pyrimido[4,5-b]quinolines), and
bis(benzo[4,5]imidazo[2,1-b]quinazolines) linked to
pyrazole units as novel hybrid molecules
Mahmoud A. E. Hawass, Sherif M. H. Sanad, Ahmed H. M. Elwahy & Ismail A.
Abdelhamid
To cite this article: Mahmoud A. E. Hawass, Sherif M. H. Sanad, Ahmed H. M. Elwahy &
Ismail A. Abdelhamid (2021): Hantzsch synthesis of bis(pyrido[2,3-d:6,5-d']dipyrimidines),
bis(pyrimido[4,5-b]quinolines), and bis(benzo[4,5]imidazo[2,1-b]quinazolines) linked
to pyrazole units as novel hybrid molecules, Synthetic Communications, DOI:
10.1080/00397911.2021.1913604
To link to this article: https://doi.org/10.1080/00397911.2021.1913604
Published online: 27 Apr 2021.
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https://doi.org/10.1080/00397911.2021.1913604
Hantzsch synthesis of bis(pyrido[2,3-d:6,5-d’]dipyrimidines),
bis(pyrimido[4,5-b]quinolines), and
bis(benzo[4,5]imidazo[2,1-b]quinazolines) linked to pyrazole
units as novel hybrid molecules
Mahmoud A. E. Hawass, Sherif M. H. Sanad , Ahmed H. M. Elwahy , and
Ismail A. Abdelhamid
Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt
ABSTRACT
ARTICLE HISTORY
Received 15 January 2021
Bis(1-phenylpyrazole-4-carboxaldehydes) were utilized as versatile
precursors to novel series of bis(pyrido[2,3-d:6,5-d’]dipyrimidines),
bis(pyrimido[4,5-b]quinolines), and bis(benzo[4,5]imidazo[2,1-b]quina-
zolines) derivatives which are linked to pyrazole units.
KEYWORDS
Bis(benzo[4,5]imidazo[2,1-
b]quinazolines); bis(pyr-
ido[2,3-d:6,5-
GRAPHICAL ABSTRACT
d’]dipyrimidines); bis(pyri-
mido[4,5-b]quinolines);
Hantzsch like reaction; 6-
aminouracil
Introduction
Uracil is a naturally occurring pyrimidine moiety and represents one of the four nucleo-
bases in the biopolymer RNA.[1–5] The uracil and its derivatives display a wide range of
bioactivities that include, treatment of viral and cancer diseases.[6–8] Also, they have a
variety of applications as antihypertensive agents,[9] antiallergics,[10,11] bronchodila-
tors,[10,11] and adenosine receptor antagonists.[12,13] Besides, uracil derivatives were used
as versatile reagents for the synthesis of a wide range of heterocyclic compounds
including,
pyrido[2,3-d]pyrimidines,[14,15]
pyrimido[4,5-d]pyrimidines,[15]
and
CONTACT Ahmed H. M. Elwahy
aelwahy@hotmail.com; Ismail A. Abdelhamid
ismail_shafy@yahoo.com
Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt.
Supplemental data for this article can be accessed on the publisher’s website
ß 2021 Taylor & Francis Group, LLC

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M. A. E. HAWASS ET AL.
Scheme 1. Attempted synthesis of bis(5,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-tetraone) 6a.
pyrimido[4,5-b]quinolines.[14,16–22] In addition, the pyrazole derivatives are found in
many pharmaceutical drugs[21–26] that exhibit anti-inflammatory properties and inhibit
alcohol dehydrogenase in addition to sildenafil phosphodiesterase.[27] Furthermore, in
the last decades, the synthesis of hybrid molecules and their evaluation as broad types
of pharmacological agents have been extensively studied.[28–36] These compounds are
characterized by linking two differently active compounds in novel scaffolds with
improved biological and medicinal applications. Multi-component reactions (MCRs) are
economically and environmentally friendly as compared to the normal multistep reac-
tions[37–41] which produce considerable amounts of waste mainly due to toxic and haz-
ardous solvents. On the other hand, MCRs provide rapid access to organic compounds
with higher simplicity, selectivity, atom-economy and an overall efficiency.[37–41] With
reference to the significance of the uracil and pyrazole moieties and in conjunction to
our work on Michael addition,[42–46] Hantzsch reactions[47–50] multicomponent reac-
tions,[48,51,52] as well as on the synthesis of bis-heterocycles[47–49,51–54] our study aims at
the synthesis of novel bis(5,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-tet-
raones), bis(5,8,9,10-tetrahydropyrimido[4,5-b]quinoline-2,4,6-triones) and bis(3,4,5,12-
tetrahydro-benzo[4,5]imidazo[2,1-b]quinazolin-1-ones) each linked to pyrazole moiety.
Results and discussion
Two strategies were assumed for the synthesis of bis(1-phenylpyrazole-3,4-diyl))bis(5,10-
dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-tetraone) 6a. In the first strategy
(Pathway A), we studied the synthesis of 5-(3-(4-hydroxyphenyl)-1-phenylpyrazol-4-yl)-
5,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-tetraone
undergo bis-alkylation reaction with 1,3-dibromopropane 5a, under basic reaction con-
ditions to give bis(1-phenylpyrazole-3,4-diyl))bis(5,10-dihydropyrido[2,3-d:6,5-
4
which should then
d’]dipyrimidine-2,4,6,8-tetraone) 6a (Scheme 1). Unfortunately, pseudo-multicomponent
reaction of 3-(4-hydroxyphenyl)-1-phenyl-1H-pyrazole-4-carboxaldehyde 1a with two
equivalents of 6-aminouracil 2a in acetic acid at reflux did not lead to the formation of

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Scheme 2. Synthesis of 5,5’-((3-aryl-1-phenylpyrazol-4-yl)methylene)bis(6-aminopyrimidine-2,4-
dione) 3b–d.
4a even after prolonged heating. Instead, the reaction afforded an inseparable mixture
of the 5,50-((3-aryl-1-phenylpyrazol-4-yl)methylene)bis(6-aminopyrimidine-2,4-dione) 3a
together with other undefined products.
It is worthy to mention that we also investigated the reactivity of other 1-arylpyra-
zole-4-carboxaldehydes 1b–d with two equivalents of either 6-aminouracil 2a or thiour-
acil 2b in acetic acid at reflux. Likewise, in all cases, the reactions did not afford the
corresponding 5,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-tetraone 4, and
instead the 5,50-((3-aryl-1-phenylpyrazol-4-yl)methylene)bis(6-aminopyrimidine-2,4-
dione) 3b–d were obtained as sole products in good to excellent yields (Scheme 2). The
1
structures of the formed products were confirmed based on the H NMR spectrum of
3b that indicated the presence of two amino groups at 6.63 ppm. Besides, it revealed the
presence of a characteristic singlet signal at d 5.45 for the methine protons. Besides, the
two broad singlets at d 10.07 and d 10.46 are assigned to the two NH groups. The pyra-
zole-H and aromatic protons appear at their expected position. The IR spectrum of
compound 3b revealed bands at ꢀ 3357, 3168, and 1630 cmꢀ1 characteristic for NH2,
NH and CO groups. Moreover, the mass spectrum of compound 3b features the correct
molecular ion peak at m/z 484.
The unsuccessful synthesis of 6 using the above strategy prompted us to study
another approach (Pathway B). This strategy includes two steps; in the first one, the
bis-aldehyde 7a was prepared as previously described[55] via the bis-alkylation reaction
of 3-(4-hydroxyphenyl)-1-phenyl-1H-pyrazole-4-carboxaldehyde 1a with the 1,3-dibro-
mopropane 5a in boiling DMF in the presence of potassium hydroxide (Scheme 3).
Subsequent acid-catalyzed cyclocondensation reaction of one mole equivalent of 7a with
four mole equivalents of 6-aminouracil 2a afforded the bis(9,10-dihydropyrido[2,3-d:6,5-

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M. A. E. HAWASS ET AL.
Scheme 3. Synthesis of bis(5,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8-tetraone) 6a.
d’]dipyrimidinetetraone) 6a rather than the other possible tetrakis(aminouracil) deriva-
tive 8a (Scheme 3).
The tetrakis(aminouracil) 8a was readily excluded based on the absence of primary
1
1
amino groups in their IR as well as H NMR spectra. On the other hand, the H-NMR
spectrum of 6a revealed a singlet signal at d 5.42 for the pyridine-H5. It showed also
three different broad signals at 6.53, 10.13, and 10.50 ppm corresponding to three differ-
ent NH groups. The aromatic protons, as well as the pyrazole-H5, appear at their
expected positions at 6.87–7.85 ppm and 8.05 ppm, respectively.
Encouraged by this success, and in a trial to expand the scope of this reaction,
bis(9,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidinetetraone) derivatives 6b–e, which are
linked to alkyl spacer via phenoxy groups, were furnished through the reaction of com-
pounds 7b,c with four equivalents of either 6-aminouracil 2a or 6-aminothiouracil 2b
in acetic acid at reflux (Scheme 4). It is worth mentioning that, the bis-aldehydes 7b,c
were prepared via the bis(alkylation) of 1d with the appropriate dibromo compounds
5b,c[55] (Scheme 4).
The synthetic scope of this reaction was also demonstrated by preparing the bis(9,10-
dihydropyrido[2,3-d:6,5-d’]dipyrimidinetetraone) 6f and 6g which are linked to benzene
core via phenoxymethyl linkage by the reaction of the respective bis(1-phenylpyrazole-
4-carboxaldehyde) 7d and 7e[55] with four equivalents of 6-aminouracil 2a in acetic acid
at reflux (Scheme 5).
Exceptionally, the reaction of bis(1-phenylpyrazole-4-carboxaldehyde) 7e with 6-ami-
nothiouracil 2b yielded the cyclic aromatized product 9a, whose constitution was

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Scheme 4. Synthesis of bis(9,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidinetetraone) derivatives 6b–e.
Scheme 5. Synthesis of bis(9,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidinetetraone) 6f and 6g.
1
confirmed based on H NMR that indicated the absence of a signal for pyridine-H5 in
1
area 4–6 ppm. The H NMR spectrum of 9a indicated also only two types of NH groups
each one integrated by 2 protons at 10.13 and 10.50 ppm, respectively (Scheme 6).
Interestingly, the bis(9,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidinetetraone) 6h which
is linked to naphthalene core via phenoxymethyl linkage was also prepared when a
warm glacial acetic solution of one equivalent of the 3,30-(((naphthalene-2,6-diylbis(me-
thylene))bis(oxy))bis(4,1-phenylene))bis(1-phenylpyrazole-4-carboxaldehyde) 7f (pre-
pared as reported earlier),[55] was added to four equivalents of 2b (Scheme 7).
Apparently, the reaction mechanism depends on the fact that each formyl group
reacts with two-mole equivalents of 6-aminouracil. Thus, the reaction involves the initial
condensation of the phenylpyrazole-4-carboxaldehydes 1 or its bis-analogues 7 with one

6
M. A. E. HAWASS ET AL.
Scheme 6. Synthesis of bis(2,8-dithioxo-2,3,8,9-tetrahydropyrido[2,3-d:6,5-d’]dipyrimidine-4,6(1H,7H)-
dione) 9a.
Scheme 7. Synthesis of bis(9,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidinetetraone) 6h.
or two equivalents of the 6-aminouracil 2 producing, the unstable ylidene derivative 11
via the intermediacy of 10. The intermediates 11 then, undergo Michael-type addition
with another one or two equivalents of the 6-aminouracil 2 to afford 12, which either
tautomerize into the diamine (3 or 8) or cyclize into 13. The intermediates 13 loss NH3
yielding the final product (4 or 6). In one exceptional case, further oxidation of the lat-
ter compounds under the reaction conditions leads to the formation of the fully oxi-
dized compound 9 (Scheme 8).
The synthetic utility of bis(1-phenylpyrazole-4-carboxaldehydes) was also extended to
involve the synthesis of a new series of bis(pyrimido[4,5-b]quinolines) linked to prazole

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Scheme 8. A plausible mechanism for the synthesis of bis(pyrido[2,3-d:6,5-d’]dipyrimidines) 9.
moiety. Thus, the three-component reaction of bis(1-phenylpyrazole-4-carboxaldehydes)
7a–c with two equivalents of both 6-aminouracil 2 and dimedone 14 afforded the corre-
sponding bis(4,1-phenylene))bis(1-phenylpyrazole-3,4-diyl))bis(8,8-dimethyl-8,9-dihydro-
pyrimido[4,5-b]quinoline-2,4,6-trione) 17a–c in good yields (Scheme 9). It is worth
mentioning that the adduct 15 or the non-oxidized bis(5,8,9,10-tetrahydropyrimido[4,5-
1
b]quinoline-2,4,6-trione) 16 were readily excluded based on H NMR that indicated the
absence of amino groups in case of 15 and the absence of H-5 and NH-10 in case of 16
at their expected positions.
Mechanistically, the reaction proceeds via the initial formation of the Knoevenagel
condensation product 18, upon treatment of 14 with 7, followed by its reaction with 6-
aminouracil 2 to give intermediate 19 that either tautomerizes into 15, or 20.
Intermediate 20 undergoes cyclization involving the amino and the carbonyl group to
give 21 that eliminate water to afford 16. Subsequent oxidation under the reaction con-
ditions leads to the formation of 17 (Scheme 10). The oxidation of dihydropyridine
under reaction conditions were previously reported.[48,55]
Our study was also extended utilizing the bis(1-phenylpyrazole-4-carboxaldehydes) 7
as versatile precursors for novel bis(1-phenylpyrazole-3,4-diyl))bis(3,4,5,12-tetrahydro-
benzo[4,5]imidazo[2,1-b]quinazolin-1-ones) 23a–c. Thus, cyclocondensation reaction of

8
M. A. E. HAWASS ET AL.
Scheme 9. Synthesis of bis(8,8-dimethyl-8,9-dihydropyrimido[4,5-b]quinolinetriones) 17a–c.
Scheme 10. A plausible mechanism for the synthesis of bis(pyrimido[4,5-b]quinolinetriones) 17a–c.

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Scheme 11. A plausible mechanism for the synthesis of bis(benzo[4,5]imidazo[2,1-b]quinazolin-1-
ones) 23a–c.
bis(1-phenylpyrazole-4-carboxaldehydes) 7a, 7e, and 7f with two equivalents of both of
dimedone 14, and 2-aminobenzimidazole 22 in DMF afforded 23a–c, respectively, in
good yields (Scheme 11). The fused tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolinones
have received considerable attention and are frequently investigated due to their wide
range of bioactivities as compared to homonuclear scaffold.[56–61]
The structures of compounds 23 were confirmed based on elemental analyses as well
1
as spectral data. Thus, the H NMR spectrum of 23a showed the presence of two sin-
glets integrated by 12 protons at d 1.02 and d 1.05 assigned to four CH3 groups.
Besides, the singlet signal at 6.56 ppm is due to H12. It also revealed the NH group as a
broad singlet signal at 11.48 ppm. All other signals appeared at their expected positions.
The reaction is assumed to proceed via the intermediacy of a,b-unsaturated ketone
18 that undergo addition and condensation reactions with 2-aminobenzimidazole 22 to
afford the intermediate 24. Subsequent removal of water leads to the formation of the
target products 23 (Scheme 12).

10
M. A. E. HAWASS ET AL.
Scheme 12. Synthesis of bis(3,4,5,12-tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1-ones) 23a–c.
Conclusions
We managed to develop an efficient synthetic approach for the synthesis of novel bis(-
pyrido[2,3-d:6,5-d’]dipyrimidines), bis(pyrimido[4,5-b]quinolines) as well as bis(ben-
zo[4,5]imidazo[2,1-b]quinazolines linked to pyrazole moiety via one-pot multi-
component cyclocondensation reaction of bis(1-phenylpyrazole-4-carboxaldehydes) with
the respective (4 equiv. 6-aminouracil), (2 equiv. 6-aminouracil and 2 equiv. dimedone)
or (2 equiv. dimedone and 2 equiv. 2-aminobenzimidazole).
Experimental
Introduction
All melting points are uncorrected. IR spectra (KBr discs) were recorded on Shimadzu
1
FT-IR-8201PC spectrophotometer. H- and 13C-NMR spectra were recorded on Varian
Mercury at 300 and 75 MHz spectrophotometer, respectively, using TMS as an internal
standard and DMSO-d6 as a solvent and chemical shifts were expressed as d ppm units.
Elemental analyses were carried out on a EuroVector instrument C, H, N analyzer
EA3000 Series.
General procedure for the synthesis of 3a–3d
A solution of each of 1-phenyl-1H-pyrazole-4-carboxaldehydes (1a–1d) (1 mmol) and 6-
aminouracil 2a or 6-aminothiouracil 2b (2 mmol) in acetic acid (5 ml) was heated at
reflux for 3 h. The solid obtained was collected and recrystallized from the proper solv-
ent to give compounds 3a–d.
5,5’-((1,3-Diphenyl-1H-pyrazol-4-yl)methylene)bis(6-aminopyrimidine-2,4(1H,3H)-
dione) (3b)
Colrless solid (DMF, 73%); m.p. > 300 ꢁC, IR (KBr): tmax 3346, 3163 (br, NH2 and
1
NH), 1630 (CO), H-NMR (DMSO-d6): d 5.45 (s, 1H, CH), 6.63 (br s, 4H, 2 NH2),
7.22–7.48 (m, 8H, ArH), 7.85 (d, 2H, ArH), 8.07 (s, 1H, pyrazole-H5), 10.07 (br s, 2H,
2 NH), 10.46 (br s, 2H, 2 NH), Anal. Calcd. for C24H20N8O4 (484.48): C, 59.50; H, 4.16;
N, 23.13; found: C, 59.69; H, 3.98; N, 23.30%.

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General procedure for the synthesis of 6a–6h and 9a
A solution of each of bis(1-phenylpyrazole-4-carboxaldehydes) (7a–7f) (1 mmol) and 6-
aminouracil 2a or 6-aminothiouracil 2b (4 mmol) in acetic acid (5 ml) was heated at
reflux for 3 h. The solid obtained was collected and crystallized from the proper solvent
to give the respective compounds 6a–6h and 9a.
5,5’-(((Propane-1,3-diylbis(oxy))bis(4,1-phenylene))bis(1-phenyl-1H-pyrazole-3,4-diyl))-
bis(5,10-dihydropyrido[2,3-d:6,5-d’]dipyrimidine-2,4,6,8(1H,3H,7H,9H)-tetraone) (6a)
Yellow solid (DMF, 75%); m.p. > 300 ꢁC, IR (KBr): tmax 3347 (br, NH), 1709, 1627
(2CO), 1H-NMR (DMSO-d6): d 2.18 (br s, 2H, OCH2CH2CH2O), 4.14 (br s, 4H,
OCH2CH2CH2O), 5.42 (s, 2H, 2 CH), 6.53 (br s, 4H, 4 NH), 6.88 (d, 4H, ArH),
7.24–7.47 (m, 10H, ArH), 7.84 (d, 4H, ArH), 8.05 (s, 2H, 2 pyrazole-H5), 10.13 (br s,
4H, 4 NH), 10.50 (br s, 2H, 2 NH), 13C-NMR (DMSO-d6): d 25.9, 29.0, 64.9, 87.4,
113.8, 118.0, 119.6, 120.1, 125.7, 126.8, 129.1, 129.8, 140.2, 150.0, 151.1, 154.0, 158.1,
Anal. Calcd. for C51H38N14O10 (1006.95): C, 60.83; H, 3.80; N, 19.47; found: C, 60.97;
H, 3.64; N, 19.55%.
General procedure for the synthesis of 17a–c
A solution of each of bis(1-phenylpyrazole-4-carboxaldehydes) (7a–c) (1 mmol), dime-
done 14 (2 mmol), and 6-aminouracil 2a or 6-aminothiouracil 2b (2 mmol) in acetic
acid (5 ml) was heated at reflux for 3 h. The solid obtained was collected and crystallized
from the proper solvent to give the respective compounds 17a–c.
5,5’-(((Propane-1,3-diylbis(oxy))bis(4,1-phenylene))bis(1-phenyl-1H-pyrazole-3,4-diyl))-
bis(8,8-dimethyl-8,9-dihydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,7H)-trione) (17a)
Orange solid (DMF, 82%); m.p. 185–186 ꢁC, IR (KBr): tmax 3142 (NH), 3052 (NH),
1606, 1511 (CO), 1H-NMR (DMSO-d6): d 1.03 (s, 12H, 4CH3), 2.23 (m, 2H,
OCH2CH2CH2O), 2.50 (s, 4H, 2CH2), 2.96 (s, 4H,
2 CH2), 4.21 (t, 4H,
OCH2CH2CH2O), 6.94–7.86 (m, 16H, ArH), 8.51 (s, 2H, ArH), 8.55 (s, 2H, 2 pyrazole-
H5), 11.59 (s, 2H, 2NH), 11.99 (s, 2H, 2NH), 13C-NMR (DMSO-d6): d 28.2, 29.1, 32.8,
46.0, 51.3, 64.7, 105.3, 109.5, 115.1, 118.5, 123.0, 125.8, 127.3, 129.9, 135.0, 140.1, 150.7,
152.2, 155.0, 158.9, 162.3, 168.6, 172.5, 196.0. Anal. Calcd. for C59H50N10O8 (1027.1): C,
68.99; H, 4.91; N, 13.64; found: C, 68.71; H, 4.78; N, 13.75%.
General procedure for the synthesis of 23a–c
A solution of each of bis(1-phenylpyrazole-4-carboxaldehydes) (7a, 7e, and 7f)
(1 mmol), dimedone (2 mmol), and 2-aminobenzimidazole 22 (2 mmol) in acetic acid
(5 ml) was heated at reflux for 3 h. The solid obtained was collected and crystallized
from the proper solvent to give the respective compounds 23a–c.

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M. A. E. HAWASS ET AL.
12,12’-(((Pentane-1,5-diylbis(oxy))bis(4,1-phenylene))bis(1-phenyl-1H-pyrazole-3,4-
diyl))bis(3,3-dimethyl-3,4,5,12-tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-
one) (23a)
Yellow solid (Ethanol, 77%); mp. 201–202 ꢁC, IR (KBr): tmax 3395 (NH), 1618, 1569
1
(CO), H-NMR (, DMSO-d6): d 1.02 (s, 6H, 2CH3), 1.05 (s, 6H, 2CH3), 1.65 (br s, 2H,
OCH2CH2CH2CH2CH2O), 1.87 (br s, 4H, OCH2CH2CH2CH2CH2O), 2.21 (m, 4H, 2
CH2), 2.57–2.63 (m, 4H, 2 CH2), 4.12 (br s, 4H, OCH2CH2CH2CH2CH2O), 6.56 (s, 2H,
2 CH), 6.78 ꢀ 7.93 (m, 26H, ArH), 8.54 (s, 2H, 2 pyrazole-H5), 11.47 (br s, 2H, 2 NH).
Anal. Calcd. for C67H62N10O4 (1071.3): C, 75.12; H, 5.83; N, 13.07; found: C, 75.01; H,
5.99; N, 12.98%.
ORCID
Sherif M. H. Sanad
Ahmed H. M. Elwahy
Ismail A. Abdelhamid
http://orcid.org/0000-0002-0186-6418
http://orcid.org/0000-0002-3992-9488
http://orcid.org/0000-0003-1220-8370
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