Survey Reactivity of Some Substituted Quinazolinones with Pentafluoro(chloro)pyridine

Article abstract of DOI:10.1002/jhet.3067

A new series of 4-hetroaryl substituted quinazolines were designed and synthesized by the reaction of pentafluoro(chloro)pyridine and 2-substituted quinazolinone. The aromatic nucleophilic substitution of pentafluoro(chloro)pyridine with quinazolinone occurs at the 4-position of pyridine ring by the oxygen site (O-centered nucleophile) of quinazolinone. The structures of all the compounds were confirmed by IR, ¹H NMR, ¹⁹F NMR, and ¹³C NMR spectroscopy as well as elemental analysis.

Full text of DOI:10.1002/jhet.3067

Month 2017
Survey Reactivity of Some Substituted Quinazolinones with
Pentafluoro(chloro)pyridine
*
Reza Ranjbar-Karimi,
Tayebeh Davodian, and Hossein Mehrabi
Department of Chemistry, Faculty of Science, Vali-e-Asr University, Rafsanjan 77176, Iran
*
E-mail: r.ranjbarkarimi@vru.ac.ir
Received July 5, 2017
DOI 10.1002/jhet.3067
Published online 00 Month 2017 in Wiley Online Library (wileyonlinelibrary.com).
A new series of 4-hetroaryl substituted quinazolines were designed and synthesized by the reaction of
pentafluoro(chloro)pyridine and 2-substituted quinazolinone. The aromatic nucleophilic substitution of
pentafluoro(chloro)pyridine with quinazolinone occurs at the 4-position of pyridine ring by the oxygen site
1
(O-centered nucleophile) of quinazolinone. The structures of all the compounds were confirmed by IR, H
NMR, 19F NMR, and 13C NMR spectroscopy as well as elemental analysis.
J. Heterocyclic Chem., 00, 00 (2017).
INTRODUCTION
substituted, but in the vast majority of reported cases,
reactions of nucleophiles are regiospecific and give
products arising from substitution of fluorine attached to
the most activated site para to the nitrogen ring [5].
Overall results were shown that the site reactivity order
of pentafluoropyridine toward nucleophilic attack was
explained on the basis of hard–hard interaction
principle, nature of nucleophile, reaction condition, and
solvent that were summarized and discussed in
documents [9–12].
Quinazolinones and many substituted quinazolinone
derivatives possess a wide range of biological activities
[13], including anti tubercular, antibacterial, anticonvulsant,
anticancer, and anti-inflammatory [14–19]. Also, structure
activity relationship studies of quinazolinone derivatives
have revealed that substitution at 4-position of the
quinazolinone ring can improve their antimicrobial and
anticancer activities [20–25]. The most common method
for the synthetic of quinazolinone derivatives is by the
condensation of anthranilic acid with amides or primary
amines [26]. Continuing our research on the chemistry of
perhalo compounds, we would like to report the site
selectivity of some substituted quinazolinone derivatives,
as bidentate nucleophiles, in the reaction with
pentafluoro(chloro)pyridine.
Heterocyclic compounds have occupied an important
place in organic chemistry, and their derivatives have
attracted considerable interests in recent years for their
versatile properties in chemistry and medicine.
Manipulating their structures makes such systems highly
amenable to drug discovery and accounts for the
widespread occurrence of active compounds containing a
heterocyclic core [1,2]. Especially perhalogenated
aromatic compounds are a class of heterocyclic that has
drawn much attention due to their potential in organic
chemistry, as a building block for the synthesis of
other heterocyclic, agrochemical, and veterinary products
[3,4], and possess biological and pharmaceutical activities
[5–8]. Much research effort has evolved around
developing synthetic utility of pentafluoropyridine and
pentachloropyridine. In the last few years, we have been
pursuing investigations on the regiochemistry of
nucleophile substitution reaction of various nucleophiles
such as N-centered, O-centered, and C-centered
nucleophiles with perfluoro(chloro)hetero analogue
aromatic systems. However, these systems readily
undergoes nucleophilic substitution at the 4-position of
pyridine ring, and all five fluorine atoms may be
© 2017 Wiley Periodicals, Inc.

R. Ranjbar-Karimi, T. Davodian, and H. Mehrabi
Vol 000
RESULTS AND DISCUSSION
observation showed that nucleophile derived from 5a
reacts with pentafluoropyridine from the oxygen site. The
IR spectrum of 7a showed the absence of NH and
To obtain the title compounds 7, we began our studies
by the preparation of several quinazolinones. According
to a reported method [27], precursor’s amidoximes 3a–e
can be prepared from the reaction of carbonitriles 1a–e
with hydroxylamine 2. In this paper, we have synthesized
these compounds under ultrasonic irradiation in short
reaction time and in high yields (Scheme 1). Also,
precursor quinazolinones 5a–e were synthesized by using
reported methods [28] from the reaction of antranilic acid
4 and amidoximes 3a–e (Scheme 1). The structure of
amidoximes and quinazolinones was characterized by
comparison of their melting points with those of
authentic samples [25,29–33].
Table 1
Optimization of reaction conditions for the formation of 7aa.
Firstly, we tried to investigate the chemoselectivity
Entry
Solvent
CH3CN
H2O
DMF
T (°C)
Yield (%)
of
reaction
of
pentafluoropyridine
6a
with
quinazolinone 5a. The formation of three types of
monosubstituted derivatives of quinazolinone 5a is
theoretically possible: 4-((perfluoropyridin-4-yl)oxy)
quinazoline (7a), 1-(perfluoropyridin-4-yl)quinazolin-
4(1H)-one (8a), and 3-(perfluoropyridin-4-yl)quinazolin-
4(3H)-one (9a) (Scheme 2).
The reaction of pentafluoropyridine 6a with
quinazolinone 5a, in the presence of potassium carbonate
at acetonitrile, gave the desired 3-(perfluoropyridin-4-yl)
quinazolin-4(3H)-one 7a (Table 3, entry 1), arising from
the substitution of the most activated fluorine atom at the
4-position of the pyridine ring, in almost quantitative
yield after purification using plate chromatography eluted
with ethyl acetate/n-hexane. 1H NMR, 13C NMR, 19F
NMR, and IR analysis confirmed product 7a. This
1
2
3
4
5
6
7
8
r.t
r.t
r.t
r.t
10
No reaction
Trace
THF
5
No reaction
15
Trace
5
Ethanol
CH3CN
H2O
DMF
THF
Ethanol
CH3CN
H2O
DMF
THF
r.t
50
50
50
50
50
9
10
10
11
12
13
14
15
Trace
65%
Trace
35
50
20
reflux
reflux
reflux
reflux
reflux
Ethanol
aConditions: 5a (1 mmol, 146 mg), 6a (1 mmol, 169 mg), K2CO3
(1.5 mmol, 208 mg), and solvent (5 mL).
Bold entry indicates optimum reaction condition.
Scheme 1. Synthesis of 4(3H)-quinazolinone derivatives.
Scheme 2. Three possible products from reaction of 5a and 6a.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
Survey Reactivity of Some Substituted Quinazolinones with
Pentafluoro(chloro)pyridine
carbonyl groups signal; instead, it exhibited an absorption
band due to the stretching band of C═N group in the
range of 1601–1670 cmꢀ1 similar to absorption band
observed for analogue compounds [24]. The complete
absence of the band for (NH) indicated the formation of
oxy compound such as reference [34]. Two resonances
by 19F NMR indicate the displacement of fluorine atom
attached to the 4-positions of the pentafluoropyridine
ring. Chemical shifts of fluorines ortho and meta to the
3-(perfluoropyridin-4-yl)quinazolin-4(3H)-one 7a using
pentafluoropyridine 6a and quinazolinone 5a (Table 1).
In the first instance, the effect of solvent and temperature
on the yield of the product was evaluated. Among
various solvents tested, CH3CN yielded the best results,
whereas DMF and THF gave the products in low yields
(Table 1, entries 1, 3, and 4) and solvents such as EtOH
and water were ineffective (Table 1, entries 2 and 5). The
reaction gave good yield in CH3CN at reflux temperature,
and the yield of reaction was reduced with decrease of
temperature (Table 1, entry 11). Next, we investigated the
effect of mole ratio of base on the synthesis of
3-(perfluoropyridin-4-yl)quinazolin-4(3H)-one. We found
that the yield improved when the reaction of
pentafluoropyridine 6a with quinazolinone 5a in the
presence of K2CO3 was carried out in mole ratio of 1:1:1.5
respectively (Table 2, entry 3). The yield was highly
dependent upon the reaction temperature, solvent, and the
mole ratio of base. The optimum reaction condition for the
synthesis of 3-(perfluoropyridin-4-yl)quinazolin-4(3H)-one
7a was found to be pentafluoropyridine (1 equiv),
quinazolinone (1 equiv), and K2CO3 (1.5 equiv), at reflux
temperature with CH3CN as the solvent (Table 1, entry 11).
In order to explore the scope of this aromatic nucleophilic
substitution, we examined the reaction of a variety of
substituted quinazolinones 5b–e with pentafluoropyridine
6a under optimized reaction conditions (Table 3). In
general, all reactions were clean, and products 7b–e were
obtained in moderate yields and characterized by different
spectroscopic methods. Also, for further development, we
studied reactions of substituted quinazolinones 5a–e with
ring nitrogen were located at
δ
=
ꢀ86.4 and
ꢀ143.6 ppm, respectively. Expansion of 1H NMR
spectrum further confirmed the structure of this
compound that gave an interesting feature of protons; five
peaks at δ = 7.64, 7.84, 7.90, 7.94, and 8.38 ppm for
protons of quinazoline ring. The13C NMR spectrum of
this compound was in good agreement with the
structure assigned. With this encouraging result in hand,
we performed the reaction of pentafluoro(chloro)
pyridine 6 with quinazolinones 5. Initially, we optimized
the reaction conditions for the synthesis of
Table 2
Optimization of the base in formation of 7aa.
Entry
Molar ratio K2CO3
Yield (%)
1
2
3
4
—
1
1.5
2
17
35
65
65
aConditions: 5a (1 mmol, 146 mg), 6a (1 mmol, 169 mg), and in CH3CN
(5 mL) under reflux for 8 h.
Table 3
Reaction of 5 with 6a.
Entry
R
X
Product
Time (h)
mp (°C)
Color
White
White
Cream
White
Oil
White
Yellow
Brown
Cream
Brown
Yield (%)
1
2
3
4
5
6
7
8
9
H (5a)
Ph (5b)
F
F
F
F
F
7a
7b
7c
7d
7e
7f
7g
7h
7i
4
6
12
10
20
6
179
138
253
179
Oil
223.6
194
239
253
203.5
65
46
40
48
43
55
35
35
40
47
CH2Ph (5c)
p-F-C6H4 (5d)
C6H11 (5e)
H (5a)
Cl
Cl
Cl
Cl
Cl
Ph (5b)
5
CH2Ph (5c)
p-F-C6H4 (5d)
C6H11 (5e)
12
10
24
10
7j
aConditions: 5a (1 mmol, 146 mg), 6a (1 mmol, 169 mg), K2CO3 (1.5 mmol, 208 mg), and in CH3CN (5 mL) under reflux for 8 h.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

R. Ranjbar-Karimi, T. Davodian, and H. Mehrabi
Vol 000
Scheme 3. General scheme for reaction of 5 with 6.
pentachloropyridine 6b (Table 3, entry 7f–j). The reaction
of pentachloropyridine 6b with quinazolinone 5a, in the
presence of potassium carbonate at acetonitrile, gave the
desired 3-(perfluoropyridin-4-yl)quinazolin-4(3H)-one 7f
(Table 3, entry 6), arising from the substitution of the most
activated chlorine atom at the 4-position of the pyridine
ring, in almost quantitative yield after purification using
plate chromatography eluted ethyl acetate/n-hexane. The
IR spectrum of 7f showed the absence of NH and
carbonyl groups; instead, it exhibited an absorption band
due to the stretching band of C═N group in the range of
1610–1665 cmꢀ1, similar to absorption band observed for
regioselectivity of nucleophilic substitution in this
process may be explained by the high nucleophilicity of
the oxygen atom of the quinazolinone ring and by the
activating influence of the nitrogen of pyridine ring that
significantly activates the ortho and para sites to itself.
EXPERIMENTAL
All materials were purchased from Sigma-Aldrich and
Merck (Tehran, Iran) and were used without any additional
purification and solvents were dried according to literature.
FT-IR spectra of all the final products were recorded on a
Bruker instrument by using the KBr self-supported pellet
technique. 1H NMR spectra were recorded at 500 and
300 MHz.13C NMR spectra were recorded at 125 and
75 MHz.19F NMR spectra were recorded at 376 and
282 MHz. NMR spectra were obtained in solution of
DMSO-d6 and CDCl3 using tetramethylsilane as internal
standard. Melting points were recorded at atmospheric
pressure, and thin-layer chromatography (TLC) analysis
was performed on silica gel TLC plates (Merck).
1
analogue compound 7a. H NMR spectra of 7f showed
five peaks at δ = 7.73, 7.87, 8.03, 8.28, and 8.39 ppm for
protons of quinolone ring. Similarly, the reactions of
quinazolinones 5a–e with pentachloropyridine 6b give
7f–j, respectively.
According to Meisenheimer intermediate [35],
a
plausible reaction mechanism is shown in Scheme 3.
Firstly, 5 deprotonated by K2CO3 and generates an anion
with three resonance forms: A, B, and C. It is clear that
the oxygen atom in A is a better nucleophile than the
nitrogen atoms in B or C because of more electron density
of the oxygen atom that occurs via aromatization of
pyrimidine ring in A as well as the less hinderers around
the oxygen atom in A. Then A reacts with 6 to give the
final product 7 arising from selective displacement of
fluorine or chlorine located at the 4-position.
General procedure for the preparation of quinazolinone
derivatives 5.
A mixture of nitrile 1 (2 mmol) and
hydroxylamine 2 (3 mmol) was sonicated for 30 min. The
progress of the reaction was monitored by TLC; after nearly
complete conversion into an intermediate presumed to be
the corresponding amidoxime 3 (as indicated by TLC),
anthranilic acid 4 (2 mmol) was added to the reaction
mixture, which was stirred at 150°C for a further 2 h. Next,
the reaction mixture was cooled to room temperature, and
the product was purified by recrystallization from ethanol.
CONCLUSION
In conclusion, we showed that pentafluoropyridine and
pentachloropyridine can successfully react with
substituted quinazolinone from the oxygen site. The
General procedures for reaction of
pentafluoro(chloro)pyridine 6.
5
with
In round-bottomed flask
charged with the quinazolin-4(3H)-one 1 (0.148 g,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2017
Survey Reactivity of Some Substituted Quinazolinones with
Pentafluoro(chloro)pyridine
1 mmol), in dry CH3CN (5 mL), and potassium carbonate
(1.5 mmol), after stirring at room temperature for 30 min,
pentafluoro(chloro)pyridine 6 (1 mmol) was added, and
the resulting mixture was stirred and refluxed for 8 h.
After completion of reaction, resulting mixture was
extracted with dichloromethane (2 × 20 mL). Removal of
the solvent in vacuum and purification of the residue by
silica gel column chromatography with ethyl acetate: n-
Hexane (4:1) afforded the desired product 7.
115.7, 115.9, 123.0, 128.0, 128.8, 130.5, 132.3, 132.4,
1
136.1, 140.4 (dm, JCF = 248 Hz, C-20,60), 142.2, 144.0
1
(dm, JCF = 230 Hz, C-30,50), 152.4, 157.3, 163.2, 163.3,
165.2 ppm. 19F NMR (282 MHz, CDCl3): δ = ꢀ152.15 (m,
2F, F3,5), ꢀ109.64 (m, 4-F), ꢀ90.04 (m, 2F, F2,6) ppm.
2-cyclohexyl-4-((perfluoropyridin-4-yl)oxy)quinazoline 7e.
43%; Oil, (Found: C, 60.20; H, 3.82; N, 10.88;
C19H15F4N3O requires C, 60.48; H, 4.01; N, 11.14). FT-
IR (KBr) (νmax, cmꢀ1): 3008 (C–H), 2925 (═C–H), 1633
(C═N), 1556 (C═C). 1H NMR (300 MHz, CDCl3):
δ = 1.20–1.90 (m, 10H), 3.46 (m, 1H), 7.42–8.40 (m, 4H)
ppm. 13C NMR (75 MHz, CDCl3): δ = 22.3, 25.2, 30.6,
42.7, 120.8, 125.6, 125.8, 126.5, 126.6, 127.3, 128.7,
4-((perfluoropyridin-4-yl)oxy)quinazoline 7a. 65%; white
crystal, mp 179°C. (Found: C, 52.67; H, 1.54; N, 14.02;
C13H5F4N3O requires C, 52.89; H, 1.79; N, 14.23). FT-IR
(KBr) (νmax, cmꢀ1): 3097 (═C–H), 1647 (C═N), 1586
1
1
(C═C). H NMR (500 MHz, CDCl3): δ = 7.64 (t, 1H,
131.3, 134.2 (dm, JCF = 248 Hz, C-20,60), 134.5 (dm,
J = 7 Hz), 7.84 (d, 1H, J = 8 Hz), 7.90 (t, 1H, J = 7 Hz),
7.94 (s, 1H), 8.38 (d, 1H, J = 8 Hz) ppm. 13C NMR
(125 MHz, CDCl3): δ = 121.6, 127.8, 128.0, 128.2, 128.6,
1JCF = 230 Hz, C-30,50), 148.5, 168.8 ppm.19F NMR
(282 MHz, CDCl3): δ = ꢀ152.09 (m, 2F, F3,5), ꢀ90.27
(m, 2F, F2,6) ppm.
1
135.8, 138.2 (dm, JCF = 248 Hz, C-20,60), 142.3, 143.7
4-((perchloropyridin-4-yl)oxy)quinazoline 7f. 55%; white
powder, mp 223.6°C. (Found: C, 42.98; H, 1.31; N,
11.43; C13H5Cl4N3O requires C, 43.25; H, 1.40; N,
11.64). FT-IR (KBr) (νmax, cmꢀ1): 2924(═C–H), 1601
(C═N), 1565 (C═C). 1H NMR (300 MHz, CDCl3):
δ = 7.73 (t, 1H, J = 7.8 Hz), 7.87 (d, 1H, J = 8 Hz), 8.03
(t, 1H, J = 7.8 Hz), 8.28 (d, 1H, J = 8 Hz), 8.39 (s, 1H)
ppm. 13C NMR (75 MHz, CDCl3): δ = 121.4, 127.1,
128.4, 129.1, 130.4 136.6, 144.8, 145.0, 146.3, 147.7,
158.3 ppm.
4-((perchloropyridin-4-yl)oxy)-2-phenyl quinazoline 7g.
35%; yellow solid, mp 194°C. (Found: C, 51.89; H, 1.79;
N, 9.48; C19H9Cl4N3O requires C, 52.21; H, 2.08; N,
9.61). FT-IR (KBr) (νmax, cmꢀ1): 2920 (═C–H), 1627
(C═N), 1582 (C═C). 1H NMR (300 MHz, CDCl3):
δ = 7.50–7.59 (m, 4H), 7.73 (d, 1H, J = 6.4 Hz), 7.81–
7.84 (m, 1H), 8.14–8.18 (m, 3H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 122.0, 124.8, 128.6, 128.8, 129.4,
129.7, 131.5, 136.4, 138.2, 167.5, 171.1, 175.1 ppm.
2-benzyl-4-((perchloropyridin-4-yl)oxy)quinazoline 7h.
35%; brown powder, decompose: 239°C. (Found: C,
53.00; H, 2.17; N, 9.04; C20H11Cl4N3O requires C, 53.25;
H, 2.46; N, 9.31). FT-IR (KBr) (νmax, cmꢀ1): 3068 (C–H),
2928 (═C–H), 1645 (C═N), 1596 (C═C). 1H NMR
(300 MHz, CDCl3): δ = 3.29 (s, 2H, CH2), 8.21–8.07 (m,
9H) ppm. 13C NMR (75 MHz, CDCl3): δ = 37.9, 120.0,
125.7, 125.8, 125.9, 127.8, 128.0, 128.1, 128.2, 128.4,
128.5, 128.6, 128.7, 129.0, 130.6, 141.7, 147.0, 149.2,
(dm, 1JCF = 230 Hz, C-30,50), 147.2, 158.2 ppm. 19F NMR
(282 MHz, CDCl3): δ = ꢀ143.69 (m, 2F, F3,5), ꢀ86.40
(m, 2F, F2,6) ppm.
4-((perfluoropyridin-4-yl)oxy)-2-phenyl quinazoline 7b.
46%; white powder, mp 138°C. (Found: C, 61.40; H,
2.19; N, 11.17; C19H9F4N3O requires C, 61.46; H, 2.44;
N, 11.32). FT-IR (KBr) (νmax, cmꢀ1): 2924 (═C–H), 1630
(C═N), 1596 (C═C). 1H NMR (500 MHz, CDCl3):
δ = 7.44–7.48 (m, 3H), 7.70 (t, 1H, J = 8 Hz), 7.99 (t, 1H,
J = 8 Hz), 8.12 (d, 1H, J = 8 Hz), 8.24 (d, 2H, J = 6 Hz),
8.37 (d, 1H, J = 8 Hz) ppm. 13C NMR (125 MHz,
CDCl3): δ = C 110.0, 123.1, 123.2, 125.7, 127.6, 128.2,
1
128.3, 128.6, 131.0, 134.8, 134.9 (dm, JCF = 248 Hz, C-
1
20,60), 135.5, 140.4 (dm, JCF = 230 Hz, C-30,50), 146.7,
153.1, 154.5, 158.7 ppm. 19F NMR (282 MHz, CDCl3):
δ = ꢀ152.09 (m, 2F, F3,5), ꢀ90.15 (m, 2F, F2,6) ppm.
2-benzyl-4-((perfluoropyridin-4-yl)oxy)quinazoline 7c.
40%; cream powder, mp 253°C. (Found: C, 62.09; H,
2.55; N, 10.65; C20H11F4N3O requires C, 62.34; H, 2.88;
N, 10.91). FT-IR (KBr) (νmax, cmꢀ1): 2924 (═C–H), 1657
(C═N), 1618 (C═C). 1H NMR (300 MHz, CDCl3):
δ = 1.55 (s, 2H, CH2), 7.49–7.56 (m, 5H), 8.11–8.17 (m,
4H) ppm. 13C NMR (125 MHz, CDCl3): δ = 35.5, 109.9,
118.9, 119.4, 120.3, 120.8, 122.6, 122.9, 124.5, 125.8,
126.2, 127.1, 127.8, 128.3, 128.5, 129.8, 130.8, 136.5,
137.0, 138.6, 138.7, 140.2, 143.1, 146.2, 158.7 ppm. 19F
NMR (282 MHz, CDCl3): δ = ꢀ152.47 (m, 2F, F3,5),
151.9, 158.6 ppm.
2-(4-fluorophenyl)-4-((perchloropyridin-4-yl)oxy)
quinazoline 7i. 47%; brown powder, mp 203.5°C. (Found:
ꢀ89.51 (m, 2F, F2,6) ppm.
2-(4-fluorophenyl)-4-((perfluoropyridin-4-yl)oxy)quinazoline
7d. 48%; white crystal, mp 179°C. (Found: C, 58.65; H,
C, 49.91; H, 1.62; N, 9.03; C19H8Cl4FN3O requires C,
2.00; N, 10.42; C19H8F5N3O requires C, 58.62; H, 2.07;
N, 10.79). FT-IR (KBr) (νmax, cmꢀ1): 2925 (═C–H), 1604
(C═N), 1586 (C═C). 1H NMR (500 MHz, CDCl3):
δ = 7.33 (t, 2H, J = 7.8 Hz), 7.84–7.87 (m, 1H), 8.15 (d,
2H, J = 3.72 Hz), 8.31–8.39 (m, 2H), 8.40 (d, 1H,
J = 6.56 Hz) ppm.13C NMR (125 MHz, CDCl3): δ = 112.5,
50.15; H, 1.77; N, 9.23). FT-IR (KBr) (νmax, cmꢀ1): 2923
1
(═C–H), 1625 (C═N), 1602 (C═C). H NMR (300 MHz,
CDCl3): δ = 7.66–8.20 (m, 8H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 101.6, 103.2, 111.5, 122.1, 124.8, 128.9,
129.4, 129.7, 136.4, 138.3, 167.5, 174.7 ppm.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

R. Ranjbar-Karimi, T. Davodian, and H. Mehrabi
Vol 000
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2-cyclohexyl-4-((perchloropyridin-4-yl)oxy)quinazoline7j.
40%; cream powder, mp 253°C. (Found: C, 51.27; H, 3.24;
N, 9.31; C19H15Cl4N3O requires C, 51.50; H, 3.41; N,
9.48). FT-IR (KBr) (νmax, cmꢀ1): 3061 (C–H), 1668
(C═N), 1603 (C═C). 1H NMR (300 MHz, CDCl3):
δ = 1.22–1.92 (m, 10H), 2.78 (m, 1H), 7.45–8.37 (m, 4H)
ppm. 13C NMR (75 MHz, CDCl3): δ = 25.6, 26.8, 30.3,
42.0, 128.1, 128.3, 128.6, 129.3, 134.0, 142.7, 144.9,
146.2, 146.6, 150.9, 157.4, 168.1 ppm.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet