[Short title + Author Name - P&H title] 28 (2024) 101834

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Journal of Saudi Chemical Society

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Multistep synthesis of novel tris-Schiff bases – azobenzene hybrids as

antimicrobial agents
Omar M. Alatawi
Department of Chemistry, Faculty of Science, University of Tabuk, Tabuk 47512, Saudi Arabia

A R T I C L E I N F O A B S T R A C T

Keywords: The target compounds 4-(((1H-heteraryl)imino)methyl)-N,N-bis(4-(((4-((4-nitrophenyl) diazenyl)phenyl)imino)

Triphenyl amine methyl)phenyl)aniline (7a-q) were prepared starting with 4,4′-diformyltriphenyl amine (2) which subjected to
Azo dye react with N-bromosuccinimide to give bromodiformyltriphenyl amine (4). Compound 4 reacted with two moles
Schiff base
of 4-nitro-4′-aminoazobenzene to give the di-Schiff base 5. Compound 5 converted to its corresponding formyl
Heterocyclic amines
Antimicrobial activity
derivative 6 by reaction with n-BuLi. The reaction of the formyl derivative 6 with seventeen amino heteraryl
compounds afforded the target compounds 7a-q. All the newly prepared compounds were characterized by
different spectroscopic and elemental analyses. Compounds 7a-q were screened for their antimicrobial activities
against yeast-like fungi (C. albicans), Gram-negative (GN) bacteria (P. aeruginosa and E. coli), and Gram-positive
(GP) bacteria (S. thuringiensis and B. subtilis). Compounds 7d, 7k, 7l, and 7q showed the highest activity against
Gram-positive bacteria. The results of antimicrobial activity showed that it is highly affected by the used amine
basicity.

1. Introduction characterized by their antimicrobial properties [7,8].

Synthetic compounds known as azo dyes are made up of two frag­
ments of phenyl attached by an azo group (–N– –N–). They are made by
coupling an aromatic molecule that donates electrons with the diazo­
nium salt of a primary aromatic amine [1,2]. Azo dyes have attracted
attention for several biological uses. They are regarded as extremely
resistant to biodegradation processes and xenobiotic compounds. They
have been utilized as biological stains, textile and food colorants, and
markers of acidity and base [3,4]. Prontosil, a red azo dye, was the first
medication based on sulphonamide and was marketed in 1932. The azo
bond was employed in pharmaceutics to shield medications from unfa­
vorable side effects, such as Prontosil therapy and mouse infection
prevention against streptococcal infections. Prontosil exhibits strong
efficacy in vivo but is inactive in vitro [5,6].
The first chemotherapeutic agents that might be used to treat bac­
Because they contain antiseptic groups, some of the chemicals used
to treat textile materials biocidal also have biological activity. These
groups are appropriate for this function because they create a certain
kind of bond with the molecules of the fibrous substance. Furthermore,
it has been shown that they have biological activity against organisms
such as bacteria and fungi [9,10]. The color-dependency effect is an
intrinsic characteristic of azo derivatives with antipyrine moiety that
improves dyeability, among other advantages. Recently, Tang et al.
investigated a versatile triphenylamine (TPA) derivative that targeted
Gram-positive bacteria and showed selective sterilizing properties.
Additionally, the chemical exhibited strong anti-infective properties in
vivo and had the ability to break the cell membrane of Staphylococcus
aureus when exposed to white light [11–13].
Furthermore, Schiff bases (SBs) are the compounds with an imine or
azomethine group ( C– –N–) that are elaborately implemented in a
/\

terial infections in humans were azo-sulphonamide antimicrobial anti­
biotics. A series of azo dyestuffs with a sulphonamide functional group
was developed as potential antibacterial drugs. Azole-sulphonamide or
sulphanilamide is present in several common medications, such as
furosemide and chlorthalidone as diuretics, tolbutamide for hypogly­
cemia, and sulphonamide-trimethoprim for opportunistic infections in
AIDS patients. Azo sulphonamides are practical dyes that are
variety of applications, including dyes and pigments, catalysts, polymer
stabilizers, luminescence chemosensors, and chemical synthesis in­
termediates [14–16]. The tribological properties of SBs and their use as
bio-lubricant additives have been investigated [17,18]. Additionally,
sensors employed to identify analytes in seized samples and evaluate
illegal narcotics contain chemical processes involving SBs [19]. Many
biological actions, such as antimalarial, antiproliferative, analgesic,

E-mail address: omalatawi@ut.edu.sa.

https://doi.org/10.1016/j.jscs.2024.101834
Received 1 February 2024; Received in revised form 5 March 2024; Accepted 6 March 2024
Available online 9 March 2024
1319-6103/© 2024 The Author(s). Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license
(http://creativecommons.org/licenses/by-nc-nd/4.0/).
O.M. Alatawi
anti-inflammatory, antiviral, antipyretic, antifungal, and antibacterial
qualities, have been shown for SBs in biological chemistry [20–24]. It
seems that the imine or azomethine group ( C– –N–) is essential to their
/\
biological functions.
The antimicrobial activity of azomethine and azo functional groups
can be modulated by the substituent present on the aromatic rings.
Biologically active Schiff base compounds can be synthesized by
condensing heterocyclic compounds with at least one –NH2 group and
an aldehyde.
Because of their wide range of biological activities, pyrazole de­
rivatives are an essential class of compounds in various agricultural and
medical fields [25,26]. Additionally, they have anti-cancer properties
[27]. Imidazole derivatives, which are strong and selective antagonists
of the neuropeptide Y Y5 receptor, have antifungal and antibacterial
qualities and can be utilized as tuberculostatic medications [28–30].
Derivatives of isoxazole have immunological and immunotropic prop­
erties in addition to antifungal action against Candida albicans [31–33].
Compounds 7d and 7k, for example, exhibit strong antibacterial activity
that is comparable to the reference compounds, suggesting that they
could find application as antibacterial agents. However, the literature
has not considered the synthesis of compounds containing both Schiff
base, triphenylamine, and azobenzene fragments. The presence of N– –N,
CH– –N, and Ph3N functional groups is responsible for antimicrobial
activity.
2. Results and discussion
Synthesis of our target compounds that is, 4-(((1H-heteraryl)imino)
methyl)-N,N-bis(4-(((4-((4-nitrophenyl)diazenyl)phenyl)imino)
methyl)phenyl)aniline (7a-q) was carried out starting from 4,4′-difor­
myltriphenyl amine (2). The new Schiff base compounds 7a-q were in
vitro tested to evaluate their antimicrobial effectiveness against various
strains of bacteria and fungi. The synthetic approaches to synthesizing
new chromophores required 4,4′-diformyltriphenyl amine (2) as a key
intermediate.
Two contradictory reports of the formylation of triphenylamine with
the Vilsmeier-Haack reagents (POCl3 / DMF) were found in the litera­
ture. Wilson [34] initially stated in an early patent that the only product
of treating triphenylamine with 8.2 equiv of POCl3 in DMF was tris(4-
formylphenyl)amine (3). However, Walter and his colleagues [35]
subsequently reported that Wilson’s process produced only 4-formyltri­
phenylamine (1) and that no trialdehyde 3 was produced, even with a
long reaction time and a great excess of reagents.
With these ambiguous results in mind, we reinvestigated this for­
mylation at first using 3 equiv of POCl3 in DMF at 85 ◦ C for 20 h. Two
products, 1 and 2, were unexpectedly detected and isolated in 65 % and
30 % yields, respectively. Their configuration was assessed by lH and 13C
NMR, IR, and elemental analyses. By repeating Wilson’s procedure, we
observed that the predominant product was 4,4′-diformyltriphenyl
Fig. 1. Mono, Di, and Tri-formyltripheyl amine.
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Journal of Saudi Chemical Society 28 (2024) 101834
amine (2), not the previously reported trialdehyde (3) or monoaldehyde
(1) Fig. 1.
The dialdehyde 2 as the expected product was prepared in 71 % yield
along with a small amount of 3 (3 %) when Ph3N was treated with 10.5
equiv of POCl3 at 95–100 ◦ C for 6 h. Treatment with less excess POCl3
increased the amount of the byproduct trialdehyde.
In summary, the present work demonstrated two previously reported
results on the Vilsmeier-Haack formylation of triphenylamine to be in
error and found practical conditions for the preparation of aldehyde 2 in
good yield Fig. 1.
This work aims to use 4,4′-diformyltriphenyl amine 2 in the prepa­
ration of mixed Schiff base derivatives to evaluate their antimicrobial
activity. To achieve this target, we focused our work on the synthesis of
4,4′-diformyltriphenyl amine 2. So we started with the reaction of tri­
phenylamine under Vilsmeier Haack conditions and obtained 4,4′-
diformyltriphenyl amine which was subjected to react with N-bromo­
succinimide to afford 4,4′-[(4-bromphenyl)azanediyl]dibenzaldehyde
(BRDFTPA) 4, its 1H NMR displayed multiplet signals at δ 7.10–7.40
ppm for aromatic protons, and singlet signal at δ 9.91 ppm for aldehydic
protons (Scheme 1).
The quest for more potent antimicrobial agents has not focused much
on azo dyes. Although azo dyes have been shown to have antimicrobial
activities in a few documented cases [36,37], their potential as antimi­
crobial agents have not been thoroughly investigated, and there has
been relatively little effort put into finding azo dyes with microbial
inhibitory properties.
Therefore, we used p-aminoazobenzene derivative to synthesize a
new series of Schiff bases dye. So, when BRDFTPA was treated with 4-
nitro-4′-aminoazobenzene in ethanol afforded the Schiff base 5. The
structural formula of 5 was asserted by spectral and analytical data. IR
spectrum revealed the disappearance of two formyl function groups
around 1700 cm− 1 and instead showed a characteristic band at 1610 and
1550 cm− 1 due to the azomethine group (C– –N) and (–N– –N–) func­
tion group, respectively. The 1H NMR showed two singlet signals at δ
8.66 and 8.84 ppm for 2CH– –N– protons (Scheme 1).
When the latter compound 5 was subjected to react with n-BuLi in
DMF at − 5 to − 10 ◦ C afforded 4-(bis(4-(((4-((4-nitrophenyl)diazenyl)
phenyl)imino)methyl)phenyl)amino)benzaldehyde (6), its IR spectrum
exhibited a band at 1710 cm− 1 assigns to new carbonyl group and its 1H
NMR exhibited singlet signal at δ 9.90 ppm due to CHO proton (Scheme
2).
Now we reached our significant starting material 6 which was
treated with 17 amino heterocyclic compounds (Scheme 2) to give the
target Schiff base compounds (7a-q) that will be screened for their
antimicrobial activity and study their structure–activity relationship.
Structures 7a-q were confirmed according to their correct analytical and
spectral data. In general, their IR spectra revealed no absorption spectra
in the region around 1700 cm− 1 due to the CHO group. 1H NMR revealed
a new CH– –N– proton at δ 9.00 ppm besides two former CH– –N– at δ
O.M. Alatawi
Scheme 1. Synthesis of BRDFTPA 4 and their azo derivative 5.
8.30 ppm.
2.1. Antimicrobial behaviour
A total of thirty newly synthesizes were assessed for their in vitro
antibacterial activity versus yeast-like fungi (C. albicans), GN bacteria
(P. aeruginosa and E. coli), and GP bacteria (S. thuringiensis and B.
subtilis). The antibacterial and antifungal efficiency were evaluated
using the Agar-diffusion method. The reference drugs were cyclohexi­
mide, cephalothin, and chloramphenicol. For every studied compound,
the average diameter of the Inhibition Zones (IZ) around the disks which
represent bacterial or fungal growth was measured and recorded in
millimeters. Using the two-fold serial dilution approach, the Minimum
Inhibitory Concentration (MIC) was measured for drugs exhibiting large
growth inhibition zones (>14 mm) [38]. Table 1 contains the inhibitory
zone diameter and MIC (µg/mL).
Based on the findings presented in Table 1, most tested compounds
exhibited different inhibitory effects against antifungal strains and on
the growth of tested Gram-positive and Gram-negative bacterial strains.
Most of the compounds that were evaluated generally showed
greater effectiveness against GP (G +ve) bacteria as opposed to GN (G
− ve) bacteria. It would also be observed that the anti-microbial activity
highly affected the basicity of nitrogen heterocyclic compounds, in
which compounds belonging to pyrazole, imidazole, triazole, pyrazine,
and 1,2,4-triazine exhibited distinguished antibacterial potentials than
the other compounds.
From Table 1, the results showed that compounds 7d, 7k, 7l, and 7q
exhibited broad-spectrum antibacterial profiles against the tested or­
ganisms. According to this view, compounds 7d, 7k, 7l, and 7q had 50 %
less activity than chloramphenicol against B. thuringiensis (MIC 6.25
µg/mL) but were equipotent to it in terms of reducing the growth of B.
subtilis (MIC 3.125 µg/mL).
In terms of their ability to suppress the development of B. subtilis and
B. thuringiensis, compounds 7e, 7i, and 7m were equipotent to cepha­
lothin (MIC 6.25 µg/mL), but they only exhibited 50 % of the activity of
chloramphenicol. Conversely, MIC values (25–50 µg/mL) for com­
pounds 7b, 7c, 7e, 7h, 7g, 7j, 7n, 7o, and 7p indicated considerable
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Journal of Saudi Chemical Society 28 (2024) 101834
growth inhibitory activity against Gram-positive bacteria.
Regarding the examined Gram-negative bacteria, the majority of the
compounds showed mild growth inhibitory activity (MIC 50–100 µg/
mL). Conversely, compounds 7d and 7k showed 50 % less cephalothin
and chloramphenicol activity against P. aeruginosa and E. coli (MIC
12.5 µg/mL).
Regarding the activity of heterocyclic rings attached to triphenyl­
amine moiety against antifungal strains, the results revealed that com­
pounds 7d, 7g, 7k, 7l, 7m, and 7q exhibited moderate activity in
inhibitory the growth of B. fabae (MIC 25 µg/mL).
2.1.1. Structure-activity relationship
Regarding the structure–activity relationship as mentioned before it
was noticed that the antimicrobial activity of the tested compounds is
highly affected by the basicity of the nitrogen heterocycle rings that are
attached to the triphenylamine moiety by azomethine bond. Therefore,
the antimicrobial activity of different heterocycles can be summarized in
the following points:
1) Compounds containing one heteroatom (7a, 7l, and 7m):
By comparing the activity of compounds 7a, 7l, and 7m it is obvious
that compounds 7l and 7m are more active than 7a and this result is
because the pyridine ring in 7l and 7m is more basic than the pyrrole
ring in 7a due to the greater availability of the lone pairs on the nitrogen
atom in pyridine for proton donation.
2) Compounds containing two hetero atoms in the five-membered
ring (Compounds 7b-7h):
The order of activities against the tested organisms is as follows 7d >
7e > 7b > 7c > 7h > 7g > 7f.
Thiazole is generally more basic than oxazole but less basic than
pyrazole and imidazole. Iso oxazole is similar to oxazole in basicity, and
it is a weak base.
Pyrazole contains two nitrogen atoms in the ring. The presence of
more nitrogen atoms generally increases basicity. Pyrazole is more basic
O.M. Alatawi Journal of Saudi Chemical Society 28 (2024) 101834

Scheme 2. Synthesis of novel tris-Schiff base derivatives 7a-q.

Table 1
Antimicrobial activity of the new compounds.
MIC (µg/mL) and inhibition zone (mm)

Gram Positive bacteria (GP) Gram Negative bacteria (GN) Fungi

Compound No. B. subtilis B. thuringiensis E. coli P. aeruginosa B. fabae

7a 100 (12) 100 (14) 100 (13) 100 (14) 100 (14)
7b 12.5 (33) 25 (31) 100 (14) 100 (13) 100 (14)
7c 25 (30) 25 (30) 50 (19) 100 (15) 100 (13)
7d 3.125 (43) 6.25 (40) 12.5 (31) 50 (19) 25 (30)
7e 6.25 (36) 12.5 (31) 50 (20) 50 (20) 100 (14)
7f 100 (14) 100 (15) 100 (13) 100 (14) 50 (19)
7g 50 (19) 50 (21) 100 (14) 100 (12) 25 (30)
7h 25 (33) 25 (30) 50 (20) 100 (13) 50 (19)
7i 6.25 (35) 12.5 (31) 50 (21) 100 (14) 25 (30)
7j 25 (31) 25 (33) 100 (14) 100 (14) 100 (13)
7k 3.125 (44) 6.25 (38) 12.5 (31) 50 (21) 25 (31)
7l 3.125 (41) 6.25 (37) 25 (30) 50 (20) 25 (33)
7m 6.25 (37) 12.5 (31) 50 (21) 100 (13) 25 (30)
7n 50 (22) 100 (14) 100 (13) 100 (13) 100 (13)
7o 25 (31) 50 (20) 100 (14) 100 (14) 100 (14)
7p 50 (22) 50 (19) 50 (19) 100 (14) 100 (13)
7q 3.125 (41) 6.25 (41) 25 (30) 50 (21) 25 (31)
Chloramphenicol 3.125 (44) 3.125 (44) 6.25 (38) 6.25 (38) –
Cephalothin 6.25 (37) 6.25 (38) 6.25 (37) 6.25 (38) –
Cycloheximide – – – – 3.125 (42)

4
O.M. Alatawi
than oxazole, thiazole and isoxazole.
Imidazole also contains two nitrogen atoms in the ring and is known
for its high basicity among the mentioned compounds.
3) Compounds containing two hetero atoms in the six-membered
ring (7n, 7o, 7p):
The order of activities against the tested microorganism is as follows:
7o > 7n > 7p. Pyrazine contains two nitrogen atoms in the ring, like
pyrimidine and pyridazine, but the lone pairs of electrons on the ni­
trogen atoms contribute to basicity. Therefore, pyrazine is the most basic
compound in this series.
4) Compounds containing three heteroatoms in five-membered
rings (7i-k)
The order of activities is 7k > 7i > 7j. Compound 7j contains a 1,3,4-
oxadiazole ring which has two nitrogen atoms and an oxygen atom in
the ring. The lone pair on the nitrogen atoms can contribute to basicity,
but the electronegativity of oxygen tends to reduce the basicity, it is
generally a weak base in compound 1,3,4-thiadiazole, sulfur is less
electronegativity than of oxygen, making thiadiazol more basic. In
compound 1,3,4-triazole, the presence of three nitrogen atoms increases
basicity.
5) Comparison between compounds with high basicity (7o, 7l, 7d,
and 7k):
Compounds 7o contain a pyrazine ring, which contains two nitrogen
atoms in a cyclic structure. Compound 7l contains a pyridine ring, it has
a nitrogen atom in the heterocyclic aromatic ring and the lone pair on
this nitrogen atom makes it more basic than pyrazine.
Compound 7d Contains two nitrogen atoms in an imidazole ring, it is
more basic than pyridine. Compound 7k contains a triazole ring is the
most basic one, so, the order of activities is 7k > 7d > 7l > 7o.
3. Experimental work
3.1. The synthesis of 4,4′-diformyltriphenylamine (2) [39], 4-[4-Bromo
(4-formylphenyl) anilino]benzaldehyde (4) [40] and the outlines of 4-
bromo-N,N-bis(4-(((4-((4-nitrophenyl)diazenyl)phenyl)imino)methyl)
phenyl) aniline (5)
Were elaborated in the Supplementary file.
3.2. 4-(Bis(4-(((4-((4-nitrophenyl)diazenyl)phenyl)imino)methyl)
phenyl)amino) benzaldehyde (6)
It was obtained according to the previously reported work [39] and
the data was found in the Supplementary file.
3.3. 4-(((1H-heteraryl)imino)methyl)-N,N-bis(4-(((4-((4-nitrophenyl)
diazenyl)phenyl)imino) methyl)phenyl)aniline (7a-q)
3.3.1. General procedure
For four hours, a solution of compound 6 (1 mmol) and heterocyclic
amine (1 mmol) was refluxed in 25 mL of absolute ethanol with 4 drops
of glacial acetic acid. Compounds 7a-q were obtained by cooling the
mixture to room temperature, filtering it off, washing it with diluted HCl
and water, drying it, and recrystallizing it from ethanol.
3.4. 4-(((1H-pyrrol-2-yl)imino)methyl)-N,N-bis(4-(((4-((4-nitrophenyl)
diazenyl)phenyl) imino)methyl)phenyl)aniline (7a)
Yield, 66 %; m.p. 157–159 ◦ C; IR (KBr): νmax, cm− 1: 3100 (NH), 1620
(C–N), 1551 (N–
– –N), 1530, 1344 (NO2); 13C NMR (DMSO‑d6) δ (ppm):
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Journal of Saudi Chemical Society 28 (2024) 101834
103.5, 110.5, 114.3, 116.2 (4C), 120.0 (4C), 122.9 (4C), 124.4 (4C),
126.0 (6C), 128.8 (6C), 130.5 (3C), 145.7, 148.0 (5C), 150.5 (4C), 155.9
(2C), 158.8, 160.4 (2C). MS (m/z, %): 841 (M+, 45). Anal. Calcd for
C49H35N11O4 (841.89): C, 69.91; H, 4.19; N, 18.30 %. Found: C, 69.81;
H, 4.11; N, 18.25 %.
3.5. 4-(((1H-pyrazol-3-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl)phenyl) imino)methyl)phenyl)aniline (7b)
Yield, 71 %; m.p. 173–175 ◦ C; IR (KBr): νmax, cm− 1: 3150 (NH), 1605
(C–N),
– 1556 (N––N), 1536, 1351 (NO2); 1H NMR (DMSO‑d6) δ (ppm):
6.50 (d, 1H, C4-pyrazole), 6.90 (d, 4H, Ar-H), 7.20 (d, 6H, Ar-H), 7.50 (d,
4H, Ar-H), 7.68 (d, 6H, Ar-H), 7.80 (d, 4H, Ar-H), 8.01 (d, 1H, C5-pyr­
azole), 8.30 (d, 4H, Ar-H), 8.37 (s, 2H, 2CH– –N–), 9.00 (s, 1H,
CH––N–), 12.60 (s, 1H, NH); 13C NMR (DMSO‑d6) δ (ppm): 95.0, 116.6
(4C), 120.3 (4C), 123.1 (4C), 125.8 (4C), 126.3 (6C), 128.0 (6C), 131.0
(4C), 147.5 (5C), 150.1 (4C), 155.6 (3C), 158.2, 160.0 (2C). MS (m/z,
%): 842 (M+, 50). Anal. Calcd for C48H34N12O4 (842.88): C, 68.40; H,
4.07; N, 19.94 %. Found: C, 68.33; H, 3.99; N, 19.88 %.
3.6. 4-(((1H-pyrazol-4-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl)phenyl) imino)methyl)phenyl)aniline (7c)
Yield, 70 %; m.p. 181–183 ◦ C; IR (KBr): νmax, cm− 1: 3140 (NH), 1615
(C–N), 1552 (N–
– –N), 1539, 1350 (NO2); 1H NMR (DMSO‑d6) δ (ppm):
6.97 (d, 4H, Ar-H), 7.22 (d, 6H, Ar-H), 7.55 (d, 4H, Ar-H), 7.75 (d, 6H,
Ar-H), 7.87 (d, 4H, Ar-H), 8.35 (d, 4H, Ar-H), 8.40 (s, 2H, 2CH– –N–),
8.80 (s, 2H, pyrazole-H), 8.99 (s, 1H, CH––N–), 12.80 (s, 1H, NH). MS
(m/z, %): 842 (M+, 53). Anal. Calcd for C48H34N12O4 (842.88): C, 68.40;
H, 4.07; N, 19.94 %. Found: C, 68.32; H, 3.95; N, 19.85 %.
3.7. 4-(((1H-imidazol-2-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl) phenyl) imino)methyl)phenyl)aniline (7d)
Yield, 70 %; m.p. 168–170 ◦ C; IR (KBr): νmax, cm− 1: 3145 (NH), 1610
(C–N), 1550 (N–
– –N), 1537, 1341 (NO2); 13C NMR (DMSO‑d6) δ (ppm):
116.0 (4C), 120.0 (4C), 122.6 (4C), 124.2 (4C), 125.9 (6C), 128.4 (8C),
130.4 (3C), 137.5, 146.8 (5C), 149.5 (4C), 154.8 (2C), 159.4 (3C). MS
(m/z, %): 842 (M+, 52). Anal. Calcd for C48H34N12O4 (842.88): C, 68.40;
H, 4.07; N, 19.94 %. Found: C, 68.35; H, 3.90; N, 19.83 %.
3.8. 4-(((1H-imidazol-5-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl)phenyl) imino)methyl)phenyl)aniline (7e)
Yield, 65 %; m.p. 158–160 ◦ C; IR (KBr): νmax, cm− 1: 3130 (NH), 1609
(C–N), 1554 (N–
– –N), 1536, 1345 (NO2); 1H NMR (DMSO‑d6) δ (ppm):
6.91 (d, 4H, Ar-H), 7.06 (s, 1H, C4-imidazole), 7.20 (d, 6H, Ar-H), 7.51
(d, 4H, Ar-H), 7.60 (s, 1H, C2-imidazole), 7.70 (d, 6H, Ar-H), 7.81 (d, 4H,
Ar-H), 8.30 (d, 4H, Ar-H), 8.39 (s, 2H, 2CH– –N–), 8.75 (s, 1H,
CH– –N–), 12.95 (s, 1H, NH). MS (m/z, %): 842 (M+, 56). Anal. Calcd for
C48H34N12O4 (842.88): C, 68.40; H, 4.07; N, 19.94 %. Found: C, 68.36;
H, 3.99; N, 19.82 %.
3.9. 4-(((4-((4-Nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazinyl)phenyl)imino)methyl)phenyl)-N-(4-((oxazol-2-
ylimino)methyl)phenyl)aniline (7f)
Yield, 63 %; m.p. 168–170 ◦ C; IR (KBr): νmax, cm− 1: 1611 (C– –N),
1551 (N– –N), 1540, 1341 (NO2), 1100 (C-O-C); 1H NMR (DMSO‑d6) δ
(ppm): 6.88 (d, 4H, Ar-H), 7.12 (d, 1H, C5-oxazole), 7.35 (d, 6H, Ar-H),
7.56 (d, 4H, Ar-H), 7.61 (d, 1H, C4-oxazole), 7.73 (d, 6H, Ar-H), 7.81 (d,
4H, Ar-H), 8.28 (d, 4H, Ar-H), 8.47 (s, 2H, 2CH– –N–), 8.52 (s, 1H,
CH––N–). MS (m/z, %): 843 (M+, 60). Anal. Calcd for C48H33N11O5
(843.86): C, 68.32; H, 3.94; N, 18.26 %. Found: C, 68.27; H, 3.88; N,
18.20 %.
O.M. Alatawi
3.10. 4-((Isoxazol-3-ylimino)methyl)-N,N-bis(4-(((4-((4-nitrophenyl)
diazenyl)phenyl)imino)methyl)phenyl)aniline (7g)
Yield, 65 %; m.p. 156–158 ◦ C; IR (KBr): νmax, cm− 1: 1616 (C–
–N),
1557 (N– –N), 1549, 1343 (NO2); MS (m/z, %): 843 (M+, 63). Anal. Calcd
for C48H33N11O5 (843.86): C, 68.32; H, 3.94; N, 18.26 %. Found: C,
68.25; H, 3.85; N, 18.19 %.
3.11. 4-(((4-((4-Nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazenyl)phenyl)imino)methyl)phenyl)-N-(4-((thiazol-
2-ylimino)methyl)phenyl)aniline (7h)
Yield, 71 %; m.p. 186–188 ◦ C; IR (KBr): νmax, cm− 1: 1610 (C– –N),
1558 (N––N), 1550, 1340 (NO2), 1150 (C-S-C); 13C NMR (DMSO‑d6) δ
(ppm): 115.9 (4C), 117.9, 120.2 (4C), 123.4 (4C), 124.7 (4C), 126.1
(6C), 128.9 (6C), 130.6 (3C), 140.2, 146.6 (5C), 149.9 (4C), 155.3 (2C),
160.3 (3C), 171.4. MS (m/z, %): 859 (M+, 66). Anal. Calcd for
C48H33N11O4S (859.93): C, 67.04; H, 3.87; N, 17.92 %. Found: C, 66.88;
H, 3.79; N, 17.88 %.
3.12. 4-(((1,3,4-Thiadiazol-2-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl) phenyl) imino)methyl)phenyl)aniline (7i)
Yield, 73 %; m.p. 194–196 ◦ C; IR (KBr): νmax, cm− 1: 1613 (C–N),
–
1559 (N––N), 1555, 1343 (NO2), 1145 (C-S-C); 13C NMR (DMSO‑d6) δ
(ppm): 116.3 (4C), 118.5 (4C), 121.0 (4C), 124.1 (4C), 125.6 (6C), 127.0
(6C), 129.9 (3C), 147.6 (5C), 150.3 (5C), 153.0, 156.0 (2C), 161.1 (3C).
MS (m/z, %): 860 (M+, 50). Anal. Calcd for C47H32N12O4S (860.91): C,
65.57; H, 3.75; N, 19.52 %. Found: C, 65.49; H, 3.68; N, 19.47 %.
3.13. 4-(((1,3,4-Oxadiazol-2-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl) phenyl) imino)methyl)phenyl)aniline (7j)
Yield, 63 %; m.p. 178–180 ◦ C; IR (KBr): νmax, cm− 1: 1620 (C––N),
1560 (N––N), 1535, 1340 (NO2), 1109 (C-O-C); MS (m/z, %): 844 (M+,
61). Anal. Calcd for C47H32N12O5 (844.85): C, 66.82; H, 3.82; N, 19.90
%. Found: C, 66.77; H, 3.78; N, 19.81 %.
3.14. 4-(((1H-1,2,4-triazol-3-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl) phenyl) imino)methyl)phenyl)aniline (7k)
Yield, 78 %; m.p. 188–190 ◦ C; IR (KBr): νmax, cm− 1: 3140 (NH), 1605
(C–N),
– 1558 (N––N), 1527, 1348 (NO2); 1H NMR (DMSO‑d6) δ (ppm):
6.92 (d, 4H, Ar-H), 7.40 (d, 6H, Ar-H), 7.60 (d, 4H, Ar-H), 7.78 (d, 6H,
Ar-H), 7.85 (d, 4H, Ar-H), 8.31 (d, 4H, Ar-H), 8.50 (s, 1H, C5-triazole),
8.59 (s, 2H, 2CH––N–), 9.10 (s, 1H, CH– –N–), 13.50 (s, 1H, NH). MS
(m/z, %): 843 (M+, 60). MS (m/z, %): 843 (M+, 65). Anal. Calcd for
C47H33N13O4 (843.87): C, 66.90; H, 3.94; N, 21.58 %. Found: C, 66.84;
H, 3.87; N, 21.46 %.
3.15. 4-(((4-((4-Nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazinyl)phenyl)imino)methyl)phenyl)-N-(4-((pyridin-2-
ylimino)methyl)phenyl)aniline (7l)
Yield, 71 %; m.p. 210–212 ◦ C; IR (KBr): νmax, cm− 1: 1610 (C–N),
–
1560 (N––N), 1530, 1346 (NO2); 13C NMR (DMSO‑d6) δ (ppm): 116.4
(4C), 119.9 (2C), 120.0 (4C), 122.4 (4C), 124.8 (4C), 125.9 (6C), 128.1
(6C), 131.3 (3C), 137.4, 145.9, 148.9 (5C), 150.6 (4C), 155.7 (2C),
155.9, 158.8, 160.2 (2C). MS (m/z, %): 853 (M+, 67). Anal. Calcd for
C50H35N11O4 (853.90): C, 70.33; H, 4.13; N, 18.04 %. Found: C, 70.27;
H, 4.10; N, 17.89 %.
6
Journal of Saudi Chemical Society 28 (2024) 101834
3.16. 4-(((4-((4-Nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazinyl)phenyl)imino)methyl)phenyl)-N-(4-((pyridin-3-
ylimino)methyl)phenyl)aniline (7m)
Yield, 74 %; m.p. 195–197 ◦ C; IR (KBr): νmax, cm− 1: 1614 (C–N),–
1561 (N– –N), 1532, 1342 (NO2); 1H NMR (DMSO‑d6) δ (ppm): 6.70 (d,
4H, Ar-H), 7.25 (d, 6H, Ar-H), 7.32 (m, 1H, C5-pyridine), 7.50 (d, 4H, Ar-
H), 7.61 (d, 1H, C4-pyridine), 7.70 (d, 6H, Ar-H), 7.80 (d, 4H, Ar-H),
8.25 (s, 1H, C2-pyridine), 8.37 (d, 4H, Ar-H), 8.48 (s, 2H, 2CH– –N–),
8.60 (d, 1H, C6-pyridine), 8.90 (s, 1H, CH–
–N–). MS (m/z, %): 853 (M+,
59). Anal. Calcd for C50H35N11O4 (853.90): C, 70.33; H, 4.13; N, 18.04
%. Found: C, 70.25; H, 4.05; N, 17.92 %.
3.17. 4-(((4-((4-Nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazinyl) phenyl)imino)methyl)phenyl)-N-(4-
((pyrimidin-2-ylimino)methyl)phenyl) aniline (7n)
Yield, 68 %; m.p. 205–207 ◦ C; IR (KBr): νmax, cm− 1: 1605 (C–N), –
1554 (N––N), 1540, 1339 (NO2); 1H NMR (DMSO‑d6) δ (ppm): 6.77 (d,
4H, Ar-H), 7.35 (d, 6H, Ar-H), 7.45 (m, 1H, C5-pyrimidine), 7.53 (d, 4H,
Ar-H), 7.67 (d, 6H, Ar-H), 7.71 (d, 4H, Ar-H), 8.40 (d, 4H, Ar-H), 8.55 (s,
2H, 2CH– –N), 8.66 (d, 2H, pyrimidine-H), 8.96 (s, 1H, CH– –N–); 13C
NMR (DMSO‑d6) δ (ppm): 113.9, 117.1 (4C), 120.9 (4C), 122.9 (4C),
125.8 (4C), 126.7 (6C), 129.0 (6C), 132.1 (3C), 150.0 (5C), 151.8 (4C),
156.4 (2C), 159.9 (2C), 161.5 (3C), 168.0. MS (m/z, %): 854 (M+, 63).
Anal. Calcd for C49H34N12O4 (854.89): C, 68.84; H, 4.01; N, 19.66 %.
Found: C, 68.77; H, 3.88; N, 19.59 %.
3.18. 4-(((4-((4-nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazinyl)phenyl)imino)methyl)phenyl)-N-(4-((pyrazin-
2-ylimino)methyl)phenyl)aniline (7o)
Yield, 72 %; m.p. 215–217 ◦ C; IR (KBr): νmax, cm− 1: 1600 (C–
–N),
1555 (N– –N), 1530, 1352 (NO2); MS (m/z, %): 854 (M+, 58). Anal. Calcd
for C49H34N12O4 (854.89): C, 68.84; H, 4.01; N, 19.66 %. Found: C,
68.75; H, 3.90; N, 19.58 %.
3.19. 4-(((4-((4-nitrophenyl)diazenyl)phenyl)imino)methyl)-N-(4-(((4-
((4-nitrophenyl) diazinyl) phenyl)imino)methyl)phenyl)-N-(4-
((pyridazin-4-limino)methyl)phenyl)aniline (7p)
Yield, 66 %; m.p. 187–189 ◦ C; IR (KBr): νmax, cm− 1: 1595 (C–N),
–
1557 (N– –N), 1534, 1351 (NO2); MS (m/z, %): 854 (M+, 63). Anal. Calcd
for C49H34N12O4 (854.89): C, 68.84; H, 4.01; N, 19.66 %. Found: C,
68.76; H, 3.85; N, 19.55 %.
3.20. 4-(((1,2,4-triazin-3-yl)imino)methyl)-N,N-bis(4-(((4-((4-
nitrophenyl)diazenyl)phenyl) imino)methyl)phenyl)aniline (7q)
Yield, 73 %; m.p. 222–224 ◦ C; IR (KBr): νmax, cm− 1: 1599 (C–N),
–
1560 (N– –N), 1550 (N– –N), 1531, 1348 (NO2); 1H NMR (DMSO‑d6) δ
(ppm): 6.75 (d, 4H, Ar-H), 7.30 (d, 6H, Ar-H), 7.40 (d, 4H, Ar-H), 7.60
(d, 6H, Ar-H), 7.65 (d, 4H, Ar-H), 8.12 (d, 4H, Ar-H), 8.32 (s, 2H,
2CH– –N), 8.86 (d, 1H, C5-triazine), 8.99 (s, 1H, CH–
–N–), 9.50 (d, 1H,
C6-triazine); 13C NMR (DMSO‑d6) δ (ppm): 116.0 (4C), 120.0 (4C),
122.0 (4C), 124.7 (4C), 125.8 (6C), 128.1 (6C), 130.5 (3C), 145.2, 148.0
(5C), 150.2 (5C), 152.0, 155.0 (2C), 160.2 (3C). MS (m/z, %): 855 (M+,
69). Anal. Calcd for C48H33N13O4 (855.88): C, 67.36; H, 3.89; N, 21.28
%. Found: C, 67.29; H, 3.80; N, 21.19 %.
3.21. Antimicrobial activity
It was performed depending on the procedures reported in previous
work [41].
O.M. Alatawi
4. Conclusion
The aim of this work is to synthesize seventeen new tris-Schiff base
compounds 7a-q starting with diformyltriphenyl amine and screened for
antibacterial activity. The work involved the synthesis of bromodi­
formyltriphenyl amine (4) and the new di-Schiff base (6). The antimi­
crobial activity showed that the new compounds 7a-q are highly
dependent on the basicity of heterocyclic amines used. The more basic
amine has the highest antimicrobial activity.
Ethical approval
Not applicable.
6. Consent to participate
All authors participated directly in the current research work.
7. Consent to publish
The authors agree to publish the article under the Creative Commons
Attribution License.
8. Availability of data and materials
All relevant data are within the manuscript and available from the
corresponding author upon request.
CRediT authorship contribution statement
Omar M. Alatawi: Data curation, Formal analysis, Methodology,
Software, Investigation, Writing – review & editing, Writing-original
draft, Supervision and administration of research group.
Declaration of competing interest
The authors declare that they have no known competing financial
interests or personal relationships that could have appeared to influence
the work reported in this paper.
Appendix A. Supplementary data
Supplementary data to this article can be found online at https://doi.
org/10.1016/j.jscs.2024.101834.
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