Attempt to Synthesize Hindered 2,4,6-Tri-Aryloxy-s-Triazines: Bis(2,4-di-tert-Butylphenyl) Carbonate – Crystal Structure

Article abstract of DOI:10.1002/jccs.201700335

Some less hindered 2,4,6-tri-aryloxy-s-triazines were synthesized through the reaction of the corresponding phenols as a starting materials with cyanogen bromide (BrCN) to obtain the corresponding arylcyanates and then trimerized. Unexpectedly, 2,4-di-tert-butyl-1-cyanatobenzene derived from 2,4-di-tert-butylphenol did not trimerize but, indeed, yielded bis(2,4-di-tert-butylphenyl) carbonate. The structures of 2,4,6-tri-aryloxy-s-triazines and bis(2,4-di-tert-butylphenyl) carbonate were characterized by means of IR, ¹H, and ¹³C NMR spectroscopies. Also the structure of the latter compound was studied by X-ray crystallography.

Full text of DOI:10.1002/jccs.201700335

JOURNAL OF THE CHINESE
CHEMICAL SOCIETY
Article
Attempt to Synthesize Hindered 2,4,6-Tri-Aryloxy-s-Triazines: Bis(2,4-di-tert-
Butylphenyl) Carbonate – Crystal Structure
a
a
a
b
*
Nader Noroozi Pesyan , Elmira Kashani, Kamaleh Ghorbanzadeh and Behrouz Notash
aDepartment of Organic Chemistry, Faculty of Chemistry, Urmia University, 57159, Urmia, Iran
bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
(Received: September 27, 2017; Accepted: December 5, 2017; DOI: 10.1002/jccs.201700335)
Some less hindered 2,4,6-tri-aryloxy-s-triazines were synthesized through the reaction of the corre-
sponding phenols as a starting materials with cyanogen bromide (BrCN) to obtain the correspond-
ing arylcyanates and then trimerized. Unexpectedly, 2,4-di-tert-butyl-1-cyanatobenzene derived
from 2,4-di-tert-butylphenol did not trimerize but, indeed, yielded bis(2,4-di-tert-butylphenyl) car-
bonate. The structures of 2,4,6-tri-aryloxy-s-triazines and bis(2,4-di-tert-butylphenyl) carbonate
1
were characterized by means of IR, H, and 13C NMR spectroscopies. Also the structure of the
latter compound was studied by X-ray crystallography.
Keywords: 2,4,6-Tri-aryloxy-s-triazines; Bis(2,4-di-tert-butylphenyl) carbonate; Trimerization;
Phenol; Aryl cyanate.
INTRODUCTION
1,3,5-Triazine derivatives are a well-known class
reaction of halogenated 1,3,5-triazines,19 and (3) multi-
component reaction of cyanamid, 1,2,4-triazole, and
triethyl orthoformate for the synthesis of 1,3,5-triazine
derivatives.20 However, these methods suffer from limi-
tations of operating difficulties or tough reaction condi-
tions involving a strong base, microwave irradiation,
noble metal catalyst, and organic oxidant. The cyclotri-
merization of nitriles generally needs an excess of
amines as the co-catalysts, which could increase the
complexity of the work-up procedure, and also rather
harsh conditions of pressure (1000 atm) and tempera-
ture (200ꢀC).21,22 Lanthanum and yttrium triflate have
been used for the reaction of ammonia and aromatic
nitriles to afford 2,4,6-triaryl-s-triazines at a lower
pressure,23 but for milder reaction conditions hexyla-
mine has been used as the co-catalyst.24 Recently, new
strategies have been reported for the synthesis of 2,4,6-
triaryl-1,3,5-triazines based on the ruthenium-catalyzed
reaction of aryl methanol and amidines.25 The disad-
vantages of the strategy are the requirement of noble
metal ruthenium-based catalysts and limitation of sub-
strate suitability.
of heterocyclic compounds of significant interest
because of their widespread applications in different
fields. These s-triazine derivatives have been found to
possess a wide variety of biological properties such as
antimycobacterial,1anticancer,2,3 antitumor,4 and anti-
inflammatory activities.5 They also show biological
activity toward HIV infection,6 malaria,7 and photosyn-
thesis inhibition.8 A literature survey revealed that vari-
ous s-triazine nuclei are hormone receptor antagonists.9
Also, some of these compounds have been shown to
have applications as liquid crystals,10 building blocks
for supramolecular chemistry,11 reactive dyes,12 organic
light-emitting diodes (OLEDs),13 and chemical reagents
for selected transformations.14
The fist aryloxy-s-triazines were synthesized by
Hofmann, who obtained them by treating the phenolate
ion with cyanogen chloride.15,16 s-Triazines were fully
considered by Smolin and Rapoport.17 Despite these
extensive investigations, only a few methods have been
reported for the preparation of this type of compounds.
Generally, this goal can be realized by the following
three conventional protocols: (1) cyclotrimerization of
nitriles,18 (2) transition-metal-catalyzed coupling
This paper describes an easy method for the syn-
thesis of three sym-trisubstituted 1,3,5-triazine deriva-
tives and the crystallographic study of the unexpected
*Corresponding author. Email: n.noroozi@urmia.ac.ir; nnp403@gmail.com
J. Chin. Chem. Soc. 2017
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1

Article
Noroozi Pesyan et al.
product derived from the hindered substituent t-butyl at
the ortho position onto phenol (4). No special catalyst
was used for the cyclotrimerization, which is a major
advantage of this process.
N
O
HO
2e
1e
RESULTS AND DISCUSSION
This paper describes the synthesis of the less hin-
dered symmetrical 2,4,6-tri-aryloxy-s-triazines (3) and
the unexpected synthesis of bis(2,4-di-tert-butylphenyl)
carbonate (4) (Schemes 1 and 2). The reaction of phe-
nols (1) with BrCN afforded aryl cyanates (2) in the
presence of triethylamine in good yield.26 The trimeriza-
tion of 2 afforded 3. Unexpectedly, 2,4-di-tert-butyl-1-
cyanatobenzene derived from 2,4-di-tert-butylphenol
did not trimerize, but, instead, yielded 4. The mecha-
nism of the formation of 4 is shown in Scheme 3.
According to Scheme 3, neither compound 2e tri-
merized nor 5-(2,4-di-tert-butylphenoxy)-1H-tetrazole
(6e) was formed while the corresponding less hindered
5-aryloxy tetrazoles were synthesized.27 No catalyst was
used for the synthesis of these tetrazoles.
NH
O
Hydrolysis
4
O
5e
Scheme 3. Plausible mechanism for the synthesis
of 4.
The versatility of nuclear magnetic resonance
spectroscopy makes it an unmatched tool for the struc-
1
tural identification of compounds. The NMR (both H
and 13C) spectra of all compounds 3a–d were recorded
in CDCl3 (see Supporting information). The structures
of the synthesized compounds were characterized by
1
spectral data (IR and H NMR). Representatively, in
the IR spectra, the C N stretching vibrations of 3c
were found at 1572 and 1498 cm−1 and the aromatic
C–H stretching band was observed at 3032 cm−1
.
Chemical shift values of s-triazine (3c) protons
appeared as three different multiplets at δ 7.27, 7.09,
and 6.90 ppm, which are related to the ortho- and
meta-hydrogen atoms. Peaks at δ 2.24 and 2.19 ppm
for the methyl protons of phenyl were also observed. In
the l3C NMR spectra, the peak at 173.83 ppm is related
to the carbon atoms of the s-triazine aromatic ring.
Other peaks at 149.56, 134.25, 131.33, 121.25, 119.44,
and 117.42 ppm were related to the ipso-, ortho-, para-,
and meta-carbon atoms of the phenyl ring, respectively.
Two methyl carbon peaks appeared at δ 18.55 ppm (see
Section 3 and Supporting information).
Scheme 1. Synthesis of symmetrical 2,4,6-tri-aryloxy-
s-triazines (3).
NaN3
N
N
N
N
H
O
6e
Trimerisation
Crystallographic analysis of 4
OCN
For further investigation, the X-ray diffraction
analysis of 4 was carried out (Figure 1), and the data of
4 are summarized in Table 1, which provides the crys-
tallographic results and refinement information. The
crystal packing of 4 is shown in Figure 2. The crystal
structure of 4 indicated that this compound was formed
unsymmetrically in the solid state (see Table 2 and
O
O
O
2e
4
Scheme 2. Unexpected synthesis of bis (2,4-di-tert-
butylphenyl) carbonate (4).
2
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Attempt to Synthesis of Hindered 2,4,6-tri-...
(4) Å, respectively (Table 2, entries 2 and 3). The bond
lengths O1—C1 and O3—C16 are 1.419 (4) and 1.415
(4) Å, respectively (Table 2, entries 4 and 5). The
lengths of the two bonds between O1 and O3 with car-
bon atoms of carbonyl group are shorter than those of
two bonds O1—C1 and O3—C16. This can be due to
the resonance of the two oxygen atoms’ lone pairs
(O1 and O3) with carbonyl group in the carbonate core
(Scheme 4). The carbonate core in the structure has a
planar form. Also, two substituted phenyl rings are
nearly perpendicular to the carbonate plane. Especially,
the ortho hindered substituents forced this formation.
The crystal structure of 4 is stabilized by weak
intermolecular hydrogen bonding interactions such as
Fig. 1. ORTEP diagram of 4.
C4—H4BÁÁÁO1,
C5—H5BÁÁÁO1,
C20—H20BÁÁÁO3,
C21—H21BÁÁÁO3, and C29—H29ÁÁÁO2 (Table 3 and
Figures 1 and 3). Figure 3 indicates the compound
4 has no plane of symmetry (σ) due to the hindrance
effect of tert-butyl groups at ortho positions on the phe-
nyl rings. For instance, the two bond lengths of O1—
C15 and O3—C15 were seen at 1.341 (4) and 1.343
Figure 4).
A
colorless
single
crystal
of
size
0.5 × 0.35 × 0.3 mm was selected and mounted on a
STOE IPDS II diffractometer with graphite-
monochromatized Mo Kα radiation (λ = 0.71073 Å).
Table 1. Crystallographic data of 4
Crystal data
Chemical formula
Mr
C29H42O3
438.63
Crystal system, space group
Temperature (K)
a, b, c (Å)
Triclinic, P1
150
9.895 (2), 11.198 (2), 13.444 (3)
71.70 (3), 73.25 (3), 81.19 (3)
α, β, γ (ꢀ)
V (Å3)
1351.1 (6)
Z
2
Mo Kα
0.07
Radiation type
μ (mm−1
)
Crystal size (mm)
0.5 × 0.35 × 0.3
Data collection
Diffractometer
STOE IPDS II
Absorption correction
Numerical shape of crystal determined optically
Tmin, Tmax
0.974, 0.976
9371, 4455, 3484
0.036
No. of measured, independent and observed [I > 2σ(I)] reflections
Rint
(sin θ/λ)max (Å−1
Refinement
)
0.583
R[F2 > 2σ(F2)], wR(F2), S
No. of reflections
0.081, 0.208, 1.09
4455
302
No. of parameters
H-atom treatment
H-atom parameters constrained
1.05, −0.45
Δρmax, Δρmin (e Å−3
)
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Article
Noroozi Pesyan et al.
Fig. 2. Crystal packing diagram of 4.
Data collection was carried out by X-AREA 1.31
(Stoe & Cie GmbH, 2005),28 cell refinement by X-
AREA (Stoe & Cie GmbH, 2005), and data reduction
by X-AREA (Stoe & Cie GmbH, 2005). To solve the
structure, the program SHELXS97 (Sheldrick, 1990)29
was used and to refine the structure SHELXL97
(Sheldrick, 1997) was employed. Molecular graphics
were drawn by ORTEP-3 for Windows (Farrugia,
Fig. 3. Unsymmetrical form of 4 based on planar
carbonate core in the solid state.
Table 2. Selected bond lengths, angles, and torsion angles of 4
Entry
Atom
Bond length (Å), angle (θ) and torsion angle (φ)
1
2
3
4
5
6
7
8
O2—C15
O1—C15
O3—C15
O1—C1
O3—C16
C2—C1
C8—C9
C18—C17
1.190 (4)
1.341 (4)
1.343 (4)
1.419 (4)
1.415 (4)
1.396 (4)
1.535 (4)
1.546 (4)
1.527 (4)
127.7 (3)
127.6 (3)
104.6 (2)
117.4 (3)
117.9 (3)
123.2 (3)
122.8 (3)
−3.5 (4)
−3.7 (4)
−52.1 (4)
−60.6 (4)
7.4 (5)
9
C23—C24
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
O2—C15—O1
O2—C15—O3
O1—C15—O3
C2—C1—O1
C17—C16—O3
C1—C2—C3
C16—C17—C18
C3—C2—C1—O1
C18—C17—C16—O3
C15—O3—C16—C29
C15—O1—C1—C14
C1—O1—C15—O2
C16—O3—C15—O2
C1—O1—C15—O3
C16—O3—C15—O1
1.7 (5)
−172.6 (2)
−178.3 (2)
4
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Attempt to Synthesis of Hindered 2,4,6-tri-...
Data Center (CCDC; 1564069 registration number).
These data can be obtained free of charge from CCDC
via www.ccdc.cam.ac.uk/data_request/cif or request to
CCDC, 12 Union Road, Cambridge, UK (fax:
+44–1223-336 033, e-mail: deposit@ccdc.cam.ac.uk).
O2
O2
C1
C15
C16
C1
C15
C16
O1
O3
O1
O3
1.419 (4)
1.415 (4)
1.341 (4) 1.343 (4)
O2
EXPERIMENTAL
General information
C1
C15
C16
O1
O3
The obtained products were characterized by melt-
ing points (m.p.) as well as IR, 1H NMR, and 13C
NMR spectroscopies. IR spectra were recorded on a
NEXUS 670 FT IR spectrometer in the range
4000–400 cm−1in a KBr matrix. 1H and 13C NMR
spectra were recorded in CDCl3 and DMSO-d6 solvent
with TMS as an internal standard at δ = 0 ppm using a
Bruker 300 FT-NMR at 300 and 75 MHz at room tem-
perature, respectively. Proton coupling patterns are
described as singlet (s), doublet (d), triplet (t), multiplet
(m), and broad singlet (bs), and coupling constant(s)
are given in hertz (Hz). Melting points were measured
on an Electrothermal digital melting point apparatus
and are uncorrected. All compounds were routinely
checked by thin-layer chromatography (TLC) on
aluminum-backed silica gel plates, and visualization
was effected at 254 nm. All the reagents were purchased
from commercial sources (Merck, Fluka, Aldrich), and
used without further purification. Cyanogen bromide
was synthesized based on reported procedure.30
Scheme 4. Resonance forms of the carbonate core
in 4.
Table 3. Hydrogen bond geometry of 4 (d, Å)
D—HÁÁÁA
D—H
HÁÁÁA
DÁÁÁA
D—HÁÁÁA
C4—H4BÁÁÁO1
C5—H5BÁÁÁO1
C20—H20BÁÁÁO3
C21—H21BÁÁÁO3
C29—H29ÁÁÁO2
0.96
0.96
0.96
0.96
0.93
2.43
2.33
2.41
2.36
2.57
3.055 (4)
2.975 (4)
3.038 (4)
2.993 (4)
2.904 (5)
122
124
122
123
101
1997), and material for publication was prepared by
WinGX (Farrugia, 1999). Crystallographic data have
been deposited with the Cambridge Crystallographic
General method for the synthesis of 1,3,5-triazine
derivatives
General
(3a)
procedure
A:
2,4,6-triphenoxy-l,3,5-s-triazine
A
solution of 43.5 mL triethylamine
(0.314 mol) dissolved in 100 mL acetone was added
dropwise to a vigorously stirred solution of containing
phenol (0.3 mol) and cyanogen bromide (0.311 mol) in
ꢀ
150 mL acetone at 0 C during 60 min. The reaction
progress was monitored by TLC. The precipitated white
salt was triethylammonium hydrobromide. After com-
pletion of the reaction during 1 h, the white colored salt
was filtered and a yellow colored oily liquid was
obtained. The solvent was removed under reduced pres-
sure and kept in a refrigerator for 2 days. The yellow
oily liquid solidified, which was filtered off and washed
with few milliliters of acetone to give the triazine (3a).
The solid thus obtained was recrystallized from ethanol
Fig. 4. View of crystal structure from the a-axis
(top), b-axis (medium), and c-axis (bottom)
and weak hydrogen bonds (see also Table 3).
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Article
Noroozi Pesyan et al.
to yield the desired compounds (60% yield). White
solid, m.p. 230–231ꢀC (Lit. 232–235ꢀC),26 FT-IR
(cm−1) 3059 (C-H ar.), 1620, 1573 (C=N), 1491 (C=C),
this compound showed five kinds of weak hydrogen
bonds.
1
ACKNOWLEDGMENT
We thank the Urmia University Research Council
for supporting this work.
1375, 1204 (C─O); H NMR (300 MHz, CDCl3) δH
(ppm): 7.13 (d, 2H, J = 7.5 Hz), 7.21 (t, 1H,
J = 7.5 Hz), 7.34 (m, 2H, J = 7.5 Hz); 13C NMR
(75 MHz, CDCl3) δC (ppm): 121.39, 126.07, 129.47,
151.54, 173.66.
Supporting information
1
The IR, H, and 13C NMR spectral data for com-
pounds 3a–d and 4 and the crystallographic data for 4
are available in the online version of this article.
2,4,6-Tris (p-tolyloxy)-1,3,5-s-triazine (3b)
This com-
pound was prepared according to the general procedure
A using 4-methylphenole: White solid 55%, mp 235ꢀC.
FT-IR (KBr, cm−1): 2936, 2749, 2675, 1576, 1507,
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1H, ar.), 7.09 (d, 1H, ar., J = 8.4 Hz); 13C NMR
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Bis (2,4-di-tert-butylphenyl) carbonate (4)
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cm-1): 3100, 2842, 2977, 2783, 2438, 1700, 1629, 1465,
1
1404, 1260, 1023; H NMR (300 MHz, DMSO-d6) δH
(ppm): 1.4 (s, 9H, aliph.), 1.50 (s, 9H, aliph.), 7.12 (d,
1H, J = 7.5 Hz, ar.), 7,35 (d, 1H, J = 7.5 Hz, ar.), 7.51
(s, 1H, ar.); 13C NMR (75 MHz, DMSO-d6) δC (ppm):
29.79, 30.45, 31.76, 31.97, 116.01, 116.62, 123.14,
123.56, 134.57, 140.68, 153.78.
CONCLUSIONS
In summary, cyclotrimerization of some less hin-
dered aryl cyanates was carried out without using any
special catalyst in good yield. The hindered aryl cyanate
2,4-di-tert-butyl-1-cyanatobenzene gave bis (2,4-di-tert-
butylphenyl) carbonate. The crystallographic data of
6
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