Gold(iii) promoted formation of dihydroquinazolinones: Double X-H activation by gold

Article abstract of DOI:10.1039/d0ra06537d

An efficient 2-furyl gold-carbene promoted synthetic method was developed for the formation of dihydroquinazolinones from enynones by dual insertion of anthranilamides. In this organic transformation a new C-O and two C-N bond formations occurred and dihy

Full text of DOI:10.1039/d0ra06537d

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Gold(III) promoted formation of
dihydroquinazolinones: double X–H activation by
gold†
Cite this: RSC Adv., 2020, 10, 35681
ab
ab
ab
Veerabhushanam Kadiyala, Perla Bharath Kumar, c Komalla Sunil,
ab
Chittala Emmaniel Raju, Balasubramanian Sridhar and Galla V. Karunakar *ab
Received 28th July 2020
Accepted 14th September 2020
An efficient 2-furyl gold–carbene promoted synthetic method was developed for the formation of
dihydroquinazolinones from enynones by dual insertion of anthranilamides. In this organic
transformation a new C–O and two C–N bond formations occurred and dihydroquinazolinones were
obtained with a quaternary centre in moderate to very good yields in one-pot synthesis.
DOI: 10.1039/d0ra06537d
rsc.li/rsc-advances
Hence, the development of new synthetic methods for the
formation of dihydroquinazolinones is a limitless frontier.
Nitrogen-containing heterocyclic molecules such as quinazo- Cooperative catalysis has been established as a handy tool for
Introduction
1
8
linones have gained much attention due to their wide range of the synthesis of several biologically valuable molecules and
2
biological
and
pharmacological
applications.
Dihy- different procedures were reported for the synthesis of dihy-
3
9
1
0
droquinazolinone derivatives like fenquizone, and quinetha- droquinazolinone derivatives. Exploration of gold-catalyzed
zone are drugs for edema and hypertension. It was reported organic transformations has attracted much attention in recent
4
5
that bouchardatine exhibits antiobesity activitity, and pen- years due to their broad functional group tolerance and selec-
6
ipanoid C exhibits tobacco mosaic virus inhibition (Fig. 1). tivity for the formation of valuable heterocyclic molecules in
11
Further, substituted dihydroquinazolinone derivatives dis- one-pot reaction conditions. The recent literature indicating
7
played signicant cytotoxic activity.
that exploitation of enynal/enynone has recognised as good
donor or donor–donor carbene precursors for C–H/X–H inser-
12
tion and cyclopropanation reactions. Several reports are
available for synthesis of substituted furans from enynones in
13
presence of metal catalysts via a 5-exo-dig cyclization.
Fig. 1 Selected examples of important molecules containing dihy-
droquinazolinone core skeleton.
a
Fluoro and Agrochemicals Department, CSIR-Indian Institute of Chemical
Technology, Hyderabad, 500007, India. E-mail: gallavk@iict.res.in
b
Academy of Scientic and Innovative Research, Ghaziabad, 201002, India
c
Center for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology,
Hyderabad, 500007, India
1
†
Electronic supplementary information (ESI) available: Experimental details, H,
13
C NMR spectra and mass for the compounds. CCDC 1863534 (3a) and 1898773
(
5). For ESI and crystallographic data in CIF or other electronic format see DOI:
0.1039/d0ra06537d
Scheme 1 Synthetic transformations of enynones.
1
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intermediate was reported by Jia and Li co-workers (Scheme 1,
19
eqn (2)). Very recently, we have reported formation of tet-
raarylmethane derivatives by reaction of enynones with indoles
20
via (2-furyl) gold–carbene intermediate (Scheme 1, eqn (3)).
Scheme 2 Reaction of enynone (1a) with anthranilamides (2a) for
formation of 3a [CCDC 1863534].
21
Our current research efforts focused to explore the reactivity of
enynones under gold catalysis. We envisioned that reaction of
enynones (1) in the presence of gold-catalyst would produce
gold–carbene complex-I, which would react with anthranila-
mide (2) may give corresponding dihydroquinazolinone deriv-
ative 3 (Scheme 1, eqn (4)).
a
22
The reaction mechanism was proposed via (2-furyl) metal–
14
15
carbene intermediate would react with one nucleophile to
produce addition products (Scheme 1, eqn (1)). L ´o pez and
Vicente co-workers reported a method for synthesis of func-
tionalized furans from enynones in the presence of zinc cata-
Results and discussion
16
lyst. Recently, Zhu et al. developed metal carbene promoted
17
method for synthesis of vinyl-substituted dihydroindoles.
Hashmi and co-workers studied the stabilization effects of gold
Accordingly, we have conducted an experiment by using
substrates 1a and 2a in the presence of AuCl (Scheme 2). Very
3
interestingly, 21% yield of the corresponding product 2-(4-
benzoyl-5-phenylfuran-2-yl)-2-phenyl-2,3-dihydroquinazolin-
18
carbene complexes.
Double insertion of isocyanides to enynones produced
pyrrole-fused heterocyclic molecules via (2-furyl) metal–carbene
4(1H)-one 3a was observed. The product 3a was further
a
Table 1 Optimization of the reaction conditions
b
Yield (%)
ꢀ
0
3a
Entry
Catalyst (mol%)
Solvent
Temp ( C)
Time (h)
3a
1
2
3
4
5
6
7
8
9
[Au(JohnPhos)(MeCN)][SbF
6
](10)
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
MeCN
Toluene
MeOH
THF
28
28
28
28
100
70
70
70
70
70
28
28
28
28
28
28
80
80
80
80
80
80
80
80
80
80
80
12
12
12
12
12
24
24
24
24
24
14
14
14
14
14
14
05
12
12
12
12
12
12
12
08
48
36
45
46
42
35 c
cm
32
30 c
cm
49
48
49 c
cm
40
45
10
20
81
20
20
30
48
46
41
52
58
12
47
48
43
—
—
(C20
AuBr
KAuCl
H
15AuF
(10)
(10)
6 4 2 2 7 8
NO PS ) C H (10)
3
4
IPrAuCl (10)
AuClPPh
AuClPPh
3
(10)
(10), Selectuor (20)
—
—
3
IPrAuCl (10), Selectuor (20)
KAuCl (10), Selectuor (20)
AuCl (10), Selectuor (20)
4
—
—
—
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
3
KAuCl
KAuCl
KAuCl
KAuCl
KAuCl
KAuCl
KAuCl
4
4
4
4
4
4
4
(10), K
(10), CF
(10), Cu(OAc)
(10), K CO (1 eq.)
(10), Py N-oxide (1.2 eq.)
(10), PhI(OAc) (1.5 eq.)
2
S
2
O
8
(20)
COOH (1 eq.)
(20)
3
2
—
—
—
—
11
6
32
35
20
25
28
21
18
8
2
3
2
(10), FeCl
3
(2.0 eq.)
3
FeCl (2.0 eq.)
KAuCl
KAuCl
KAuCl
KAuCl
KAuCl
KAuCl
KAuCl
4
4
4
4
4
4
4
(10), FeCl
(10), FeCl
(10), FeCl
(10), FeCl
(10), FeCl
3
3
3
3
3
(2.0 eq.)
(2.0 eq.)
(2.0 eq.)
(2.0 eq.)
(2.0 eq.)
DMF
DCE
MeCN
MeCN
MeCN
MeCN
(5), FeCl
(7), FeCl
(10)
3
(1.0 eq.)
(1.5 eq.)
3
d
d
AgSbF
AuCl
6
3
(10)
—
a
Reaction conditions: all reactions were carried out under nitrogen atmosphere with 1a (0.15 mmol), and 2a (0.225 mmol) and solvent (2 mL) in oil
b
c
d
23
3
bath. Yields are for isolated products; eq.: equivalent. cm: complex mixture. Entries 26 and 27 were conducted without FeCl .
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a
Table 2 Scope of substituted dihydroquinazolinones (3)
presence of AuBr
and KAuCl
moderate yields of product 3a
3
4
was observed (Table 1, entries 3 and 4). Complex mixture was
obtained while reaction was performed in the presence of
IPrAuCl (Table 1, entry 5). In the presence of AuClPPh , poor
3
yields of desired product 3a was found (Table 1, entry 6). Then
reactions were conducted by utilizing gold catalysts in combi-
nation of selectuor (Table 1, entries 7–10), yields of desired
product 3a was not improved. Reactions were performed by
4 2 2 8 3
employing KAuCl in combination with K S O , CF COOH,
Cu(OAc) , K CO , pyridine N-oxide and PhI(OAc) (Table 1,
2
2
3
2
entries 11–16), moderate yield of 3a was observed. Nevertheless,
KAuCl4 and FeCl3 combination afforded very good yield of
(81%) of product 3a (Table 1, entry 17). An experiment was
conducted by utilizing only FeCl
3
, poor yields of product 3a was
0
observed along with 3a (Table 1, entry 18). Reactions were
screened by using series of solvents like toluene, MeOH, THF,
DMF and DCE, none of them gave better yield than MeCN
(Table 1, entries 19–23). When the gold-catalyst loading
decreased from 10 mol% to 5 mol% and 7 mol%, the product
yield also reduced to 52% and 58%, respectively (Table 1, entries
24 and 25). Two reactions were conducted without utilizing
FeCl and these cases poor yields of product 3a observed (Table
3
1, entries 26 and 27).
The above experiments concludes that Table 1, entry 17 is
the best suitable reaction conditions. Then substrate scope was
tested by utilizing different enynones (1a–k) with anthranila-
mide 2a under the optimal conditions. These results are
incorporated in the Table 2.
The substrates which are bearing electron-donating groups
such as 1b and 1c were tested with 2a to provide 76% and 72%
yields of corresponding products 3b and 3c, respectively.
Electron-withdrawing functional group containing enynone
such as 1d react with 2a to give the corresponding dihy-
droquinazolinone derivative 3d in 68% yield. Substrates bearing
electron-donating groups like 1e and 1f reacted with 2a to
produce 75% and 74% yields of the corresponding dihy-
droquinazolinone derivatives 3e and 3f, respectively. Both
electron-donating and electron-withdrawing functional groups
containing enynone like 1g reacted with 2a to generate the
corresponding product 3g in 71% yield. The substrates which
2
are having electron-donating groups at ortho position of R like
2
2
1
1
1
h (R ¼ 3-Me-C H ), 1i (R ¼ 3-Me-C H R ¼ 4-Me-C H ) and
6
4
6
4,
6
4
1
j (R ¼ 3-Me-C H ) reacted with 2a to provide the corre-
6
4
a
ꢀ
Reaction conditions: all reactions were carried out at 80 C under
sponding products 3h, 3i and 3j in moderate yields, respectively
nitrogen atmosphere with 1 (1.0 equiv.), and 2a (1.5 equiv.) in the
2
(
Table 2, entries 8–10). Alkyl substitution at R position con-
4 3
presence of KAuCl (10 mol%), FeCl (2.0 equiv.) and solvent (3 mL)
in oil bath; yields are for isolated products.
taining substrate like 1k produced the product 3k in 43% yield
(Table 2, entry 11).
Further, experiments were conducted to check the scope of
dihydroquinazolinone derivatives by utilizing different
substituted anthranilamides (2b–e) with enynones (1a–f). These
results were included in the Table 3. The enynone 1a was tested
with electron-donating functional group containing anthrani-
lamide 2b to give 3l in 72% yield. Electron-withdrawing func-
tional group containing anthranilamides such as 2c, 2d, and 2e
reacted with 1a to produce the corresponding dihy-
droquinazolinone derivatives 3m, 3n, and 3o in 65%, 63% and
2
2
conrmed by single crystal X-ray analysis. It is noteworthy that
in this organic transformation two C–N bonds were formed by
dual insertion of anthranilamide with a quaternary centre. This
interesting observation encouraged us to optimize this reaction
to get the better yields of the product 3a.
Gold(I) catalysts were screened with the substrates 1a with 2a
to produce moderate yields of 3a along with 3a (Table 1, entries
and 2). Whereas when experiments were conducted in the
0
1
60% yields, respectively (Table 3, entries 2–4). Enynones bearing
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a
Table 3 Scope of substituted dihydroquinazolinones (3)
Scheme 3 (a) Reaction of 1a with heteroaryl amine 2f (eqn (1)); (b)
reaction of dimethyl-(2-oxo-6-phenylhex-3-en-5-yn-3-yl)phospho-
nate 1l with 2a (eqn (2)); (c) gram scale synthesis of product 3a (eqn (3)).
such as 3r, 3s, 3t and 3u in 69%, 63%, 61% and 62% yields,
respectively (Table 3, entries 7 and 10). Electron-donating
substitutions containing enynones such as 1e and 1f reacted
with 2b under optimized reaction conditions to give the corre-
sponding products 3v and 3w in 70% and 68% yields, respec-
tively (Table 3, entries 11 and 12).
2-Amino-6-phenyl-4-(triuoromethyl)nicotinamide 2f reac-
ted with 1a to produce the corresponding product 3t in 58%
yield (Scheme 3, eqn (1)). An experiment was conducted by
employing a phosphorus substituted enynone like 1l with 2a to
provide the corresponding dihydroquinazolinone derivative 3y
in 68% yield (Scheme 3, eqn (2)). Further, one more experiment
was conducted in gram scale by utilizing 1a and 2a under
optimized reaction conditions to give the corresponding
product 3a in 74% yield (Scheme 3, eqn (3)).
Control experiments were conducted to clarify the reaction
mechanism (Scheme 4). The substrate 1a was tested under
0
optimized conditions to produce good yields of product 3a
(
0
Scheme 4, eqn (1)). A reaction was conducted by utilizing 3a
with anthranilamide 2a in the presence of gold-catalyst to
provide 32% yield of product 3a (Scheme 4, eqn (2)). Without
0
using catalyst one reaction was conducted by using 3a and 2a,
a
ꢀ
Reaction conditions: all reactions were carried out at 80 C under
nitrogen atmosphere with 1 (1.0 equiv.), and 2 (1.5 equiv.) in the
presence of KAuCl (10 mol%), FeCl (2.0 equiv.) and solvent (3 mL)
4 3
in oil bath; yields are for isolated products 3.
electron donating groups such as 1b and 1c reacted with 2b to
provide corresponding products 3p and 3q in 72% and 70%
yields, respectively (Table 3, entries 5 and 6). Fluorine
substituted enynone such as 1d reacted with 2b, 2c, 2d and 2e to
provide the corresponding dihydroquinazolinone derivatives
a
22
Scheme 4 Control experiments. Compound 5 CCDC 1898773.
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solvents were distilled using standard procedures. Unless
otherwise noted, reagents were obtained from Aldrich, Alfa
Aesar, and TCI used without further purication. Synthesis of
enynones (1a–l) were prepared by following reported
25
procedures.
General procedure for synthesis of dihydroquinazolinone
derivatives (3a)
To a 10 mL round-bottomed ask equipped with magnetic stir
Scheme 5 A plausible reaction mechanism.
bar the substrate 2-aminobenzamide 2a (0.45 mmol, 61 mg, 1.5
ꢀ
equiv.) was taken and dissolved in dry CH
3
CN (3 mL) at 80 C
(
oil bath) aer that 1,3-diphenyl-2-(3-phenylprop-2-yn-1-ylidene)
in this case product 3a was not observed (Scheme 4, eqn (3)).
Then 1a was tested with 2-(prop-2-yn-1-yloxy)benzohydrazide 4
to give 62% yield of product 5. The structure of the compound
propane-1,3-dione 1a (0.3 mmol, 100 mg, 1 equiv.) was added.
To this reaction mixture KAuCl (10 mol%, 11 mg) and FeCl
(
5
monitored by using TLC. Aer completion of the reaction, the
reaction mixture was ltered through celite plug and washed
with ethyl acetate. The ethyl acetate layer was concentrated
under reduced pressure to get crude residue which was puried
by column chromatography through silica gel using hexane and
ethyl acetate as eluent (10 : 3.5) to give 113 mg of the product 2-
4
3
ꢀ
0.6 mmol, 97 mg, 2.0 equiv.) was added and stirred at 80 C for
22
5a further charaecterized by single crystal X-ray analysis.
h under nitrogen atmosphere. Progress of the reaction was
Formation of dihydroquinazolinones can be proposed by the
reaction mechanism as shown in Scheme 5. Gold catalyst would
coordinate with enynone 1a may form complex-A, which would
further generate 2-furyl gold carbene complex-I via intra-
24
molecular of 5-exo-dig cyclised zwitterionic complex-B. Then,
0
13,14
it would produce ketone (3a ),
which would coordinate with
ferric chloride as a lewis acid in a regioselective fashion then it
would reacts with anthranilamide (2a) may generate IM-I.
Subsequent activation of IM-I by metal catalyst may lead to
cyclization to form intermediate IM-II, which would nally
afford the product 3a.
(
4
4-benzoyl-5-phenylfuran-2-yl)-2-phenyl-2,3-dihydroquinazolin-
(1H)-one 3a (81% yield). The same reaction was conducted on
a gram scale by utilizing 1a (1 g) and 2a (0.61 g) produced the
corresponding product 3a in 74% yield (1.03 g). A similar
experimental procedure was adopted for the synthesis of all the
furan containing dihydroquinazolinones (3b–y) and 5.
2
-(4-Benzoyl-5-phenylfuran-2-yl)-2-phenyl-2,3-dihy-
Conclusion
droquinazolin-4(1H)-one (3a). R : 0.5; hexane : ethyl acetate
f
In conclusion, we have established gold-catalyzed reaction of
enynones with dual insertion of anthranilamides to produce
a novel approach for synthesis of dihydroquinazolinones. It is
signicant that in this organic transformation new C–O and two
C–N bonds were formed with a quaternary centre with good
functional group tolerance.
mixture (10 : 3.5); yellow solid with 113 mg (81%) yield; melting
ꢀ
1
point: 188–190 C; H NMR (500 MHz, CDCl
.7, 1.2 Hz, 1H), 7.73–7.66 (m, 2H), 7.63–7.56 (m, 4H), 7.52–7.48
m, 1H), 7.47–7.42 (m, 3H), 7.37–7.31 (m, 3H), 7.30–7.26 (m,
H), 6.97–6.87 (m, 1H), 6.79–6.70 (m, 2H), 6.35 (s, 1H), 5.09
3
): d 7.93 (dd, J ¼
7
(
3
1
3
(br s, 1H), ppm; C NMR (100 MHz, CDCl
3
): d 191.1, 164.0,
1
1
1
2
56.3, 153.1, 145.2, 140.4, 137.5, 134.4, 133.0, 129.7, 129.6,
29.3, 129.0, 128.8, 128.4, 128.3, 128.2, 127.4, 126.9, 120.9,
Experimental section
General information
19.8, 115.1, 114.9, 114.0, 72.7 ppm; IR(KBr): n ¼ 3368, 3057,
ꢁ1
922, 1654, 1613, 1485, 1367, 1262 cm ; HRMS (ESI-TOF) m/z:
+
Reactions were carried out in oven dried reaction asks under [M + H] calcd for C31
H
21
N
2
O
3
H 471.1703, found 471.1705.
ꢁ
1
nitrogen atmosphere and also solvents and reagents were
Crystal data for 3a. C31
H
22
N
2
O
3
(M ¼470.50 g mol ):
ꢀ
ꢁ
transferred by oven-dried syringes to ambient temperature. TLC triclinic, space group P1 (no. 2), a ¼ 8.2197(2) A, b ¼ 10.4608(2)
ꢁ
ꢁ
ꢀ
ꢀ
was performed on Merck silica gel aluminium sheets using UV A, c ¼ 14.4752(3) A, a ¼ 77.0948(8) , b ¼ 79.6924(8) , g ¼
ꢀ
ꢁ
3
as a visualizing agent. Solvents were removed under reduced 81.5655(9) , V ¼ 1186.21(4) A , Z ¼ 2, T ¼ 294.15 K, m(MoKa) ¼
ꢁ1
ꢁ3
pressure. Columns were packed as slurry of silica gel in hexane 0.085 mm , D
¼ 1.317 g cm , 35 683 reections measured
calc
ꢀ
ꢀ
and ethyl acetate solvent mixture. The elution was assisted by (4.464 # 2Q # 61.018 ), 7216 unique (Rint ¼ 0.0618, Rsigma
¼
1
3
applying pressure with an air pump. C NMR spectra were 0.0518) which were used in all calculations. The nal R
1
was
1
recorded on 75, 100 and 125 MHz spectrometers. HNMR 0.0634 (I > 2s(I)) and wR
2
was 0.1669 (all data). CCDC 1863534.
spectra were recorded on 300, 400 and 500 MHz spectrometers 2-(4-Benzoyl-5-phenylfuran-2-yl)-2-(p-tolyl)-2,3-dihy-
in appropriate solvents using TMS as internal standard. The droquinazolin-4(1H)-one (3b). Following the general procedure,
following abbreviations were used to explain multiplicities: s ¼ 100 mg (0.285 mmol, 1.0 equiv.) of 1b, 58 mg (0.428 mmol, 1.5
singlet, d ¼ doublet, dd ¼ double doublet, dt ¼ doublet of equiv.) of 2a, 10 mg (10 mol%) of KAuCl4 and 92 mg
triplet, td ¼ triplet of doublet, t ¼ triplet, m ¼ multiplet, br s ¼ (0.571 mmol, 2.0 equiv.) of FeCl was used and the reaction time
3
broad singlet. All reactions were performed under nitrogen was 12 h. Aer ash column chromatography on silica gel
atmosphere with freshly distilled and dried solvents. All (eluted with R
f
: 0.5; hexane/ethyl acetate mixture 10/3.5), 105 mg
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of 3b was obtained in 76% yield as a yellow solid. Mp: 166– 2H), 6.93–6.87 (m, 1H), 6.73 (d, J ¼ 7.9 Hz, 1H), 6.69 (s, 1H),
ꢀ
1
1
1
7
6
68 C; H NMR (500 MHz, CDCl ): d 7.92 (dd, J ¼ 7.8, 1.2 Hz, 6.55–6.27 (m, 1H), 5.28–5.02 (br s, 1H), 2.37 (s, 3H), 2.30 (s,
3
1
3
H), 7.74–7.65 (m, 2H), 7.64–7.56 (m, 2H), 7.53–7.43 (m, 3H), 3H) ppm; C NMR (100 MHz, CDCl ): d 190.8, 163.8, 156.2,
.39–7.31 (m, 3H), 7.30–7.21 (m, 5H), 6.94–6.87 (m, 1H), 6.75– 152.6, 145.3, 143.8, 140.6, 139.4, 135.0, 134.2, 129.7, 129.5,
.70 (m, 2H), 6.31 (s, 1H), 5.06 (br s, 1H), 2.38 (s, 3H) ppm;
3
1
3
C
129.0, 128.9, 128.6, 128.3, 127.2, 126.9, 126.3, 120.4, 119.6,
NMR (100 MHz, CDCl
3
): d 191.1, 163.8, 156.2, 153.4, 145.3, 115.1, 114.8, 114.0, 72.6, 21.5, 21.2 ppm; IR(KBr): n ¼ 3357,
ꢁ
1
1
1
1
1
39.7, 137.6, 137.5, 134.2, 132.9, 129.6, 129.4, 129.2, 129.0, 3050, 2918, 1653, 1612, 1507, 1372, 1271, 1179 cm ; HRMS
28.37, 128.31, 128.2, 127.4, 126.8, 120.9, 119.7, 115.1, 114.8, (ESI-TOF) m/z: [M + H] calcd for C33
+
H
25
N
2
O
3
H 499.2016, found
13.8, 72.5, 21.0 ppm; IR(KBr): n ¼ 3376, 3068, 2922, 1654, 1612, 499.2023.
ꢁ
1
+
484, 1368, 1267 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for
2-(4-(4-Methylbenzoyl)-5-p-tolylfuran-2-yl)-2-p-tolyl-2,3-dihy-
droquinazolin-4(1H)-one (3f). Following the general procedure,
100 mg (0.264 mmol, 1.0 equiv.) of 1f, 54 mg (0.396 mmol, 1.5
C H N O H 485.1859, found 485.1862.
3
2
23 2 3
2-(4-Benzoyl-5-phenylfuran-2-yl)-2-(4-methoxyphenyl)-2,3-
dihydroquinazolin-4(1H)-one (3c). Following the general equiv.) of 2a, 10 mg (10 mol%) of KAuCl
procedure, 100 mg (0.273 mmol, 1.0 equiv.) of 1c, 55 mg (0.529 mmol, 2.0 equiv.) of FeCl was used and the reaction time
0.409 mmol, 1.5 equiv.) of 2a, 10 mg (10 mol%) of KAuCl and was 12 h. Aer ash column chromatography on silica gel
8 mg (0.546 mmol, 2.0 equiv.) of FeCl was used and the (eluted with R : 0.5; hexane/ethyl acetate mixture 10/3.5), 100 mg
reaction time was 12 h. Aer ash column chromatography on of 3f was obtained in 74% yield as a yellow solid. Mp: 210–
4
and 85 mg
3
(
4
8
3
f
ꢀ
1
silica gel (eluted with R : 0.5; hexane/ethyl acetate mixture 10/ 212 C; H NMR (500 MHz, CDCl ): d 7.91 (dd, J ¼ 7.4, 1.0 Hz,
f
3
3
.5), 98 mg of 3c was obtained in 72% yield as a yellow solid. 1H), 7.60 (d, J ¼ 8.0 Hz, 2H), 7.51 (d, J ¼ 8.2 Hz, 2H), 7.45 (d, J ¼
ꢀ
1
Mp: 111–113 C; H NMR (400 MHz, CDCl ): d 7.92 (d, J ¼ 8.2 Hz, 2H), 7.35–7.31 (m, 1H), 7.22 (d, J ¼ 8.0 Hz, 2H), 7.14 (d, J
3
7
.3 Hz, 1H), 7.75–7.46 (m, 6H),7.39–7.23 (m, 7H), 7.01–6.88 (m, ¼ 8.0 Hz, 2H), 7.07 (d, J ¼ 8.2 Hz, 2H), 6.92–6.88 (m, 1H), 6.71 (d,
3
3
H), 6.79–6.65 (m, 2H), 6.28 (s, 1H), 5.04 (br s, 1H), 3.83 (s, J ¼ 8.0 Hz, 1H), 6.68 (s, 1H), 6.27 (s, 1H), 5.06 (br s, 1H), 2.38 (s,
1
3
13
3 3
H), ppm; C NMR (100 MHz, CDCl ): d191.1, 163.9, 160.5, 6H), 2.30 (s, 3H) ppm; C NMR (100 MHz, CDCl ): d 190.8,
1
1
5
1
56.3, 153.3, 145.3, 137.5, 134.3, 133.0, 132.5, 129.1, 128.4, 163.9, 156.1, 152.8, 145.4, 143.7, 139.5, 139.3, 137.7, 135.0,
28.3, 128.2, 127.4, 120.9, 119.8, 115.2, 114.8, 114.0, 113.9, 72.4, 134.1, 129.7, 129.3, 128.9, 128.8, 128.2, 127.2, 126.8, 126.4,
5.3 ppm; IR(KBr): n ¼ 3285, 3058, 2925, 1655, 1609, 1507, 1368, 120.4, 119.5, 115.1, 114.8, 113.9, 72.5, 21.5, 21.2, 21.0 ppm;
ꢁ1
+
254 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for IR(KBr): n ¼ 3346, 3033, 2918, 1660, 1643, 1503, 1374,
ꢁ1 +
C H N O H 501.1808, found 501.1812.
1179 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for
H 513.2172, found 513.2176.
2-(4-Fluorophenyl)-2-(4-(4-methylbenzoyl)-5-p-tolylfuran-2-
00 mg (0.282 mmol, 1.0 equiv.) of 1d, 57 mg (0.423 mmol, 1.5 yl)-2,3-dihydroquinazolin-4(1H)-one (3g). Following the general
equiv.) of 2a, 10 mg (10 mol%) of KAuCl and 91 mg procedure, 100 mg (0.261 mmol, 1.0 equiv.) of 1g, 53 mg
0.564 mmol, 2.0 equiv.) of FeCl was used and the reaction time (0.392 mmol, 1.5 equiv.) of 2a, 10 mg (10 mol%) of KAuCl and
was 12 h. Aer ash column chromatography on silica gel 85 mg (0.523 mmol, 2.0 equiv.) of FeCl3 was used and the
eluted with R : 0.5; hexane/ethyl acetate mixture 10/3.5), 95 mg reaction time was 12 h. Aer ash column chromatography on
3
2
23 2 4
2-(4-Benzoyl-5-phenylfuran-2-yl)-2-(4-uorophenyl)-2,3-dihy-
34 27 2 3
C H N O
droquinazolin-4(1H)-one (3d). Following the general procedure,
1
4
(
3
4
(
f
of 3d was obtained in 68% yield as a yellow solid. Mp: 138– silica gel (eluted with R : 0.5; hexane/ethyl acetate mixture 10/
f
ꢀ
1
1
7
6
40 C; H NMR (400 MHz, CDCl
.73–7.47 (m, 7H), 7.39–7.24 (m, 6H), 7.17–7.06 (m, 2H), 6.98– Mp: 223–225 C; H NMR (400 MHz, CDCl
.87 (m, 1H), 6.80–6.69 (m, 2H), 6.45 (s, 1H), 5.07 (br s, 1H) ppm; 1.2 Hz, 1H), 7.63–7.55 (m, 4H), 7.50 (d, J ¼ 8.1 Hz, 2H), 7.38–7.31
3
): d 7.91 (d, J ¼ 7.4 Hz, 1H), 3.5), 96 mg of 3g was obtained in 71% yield as a yellow solid.
ꢀ
1
3
): d 7.91 (dd, J ¼ 7.7,
1
3
3
C NMR (100 MHz, CDCl
3
): d 191.0, 163.8, 162.2 (d, JC–F
¼
(m, 1H), 7.16–7.06 (m, 6H), 6.94–6.88 (m, 1H), 6.73 (d, J ¼
2
1
1
1
1
50.148 Hz), 156.4, 152.9, 145.1, 137.4, 136.4, 134.4, 133.0, 8.0 Hz, 1H), 6.70 (s, 1H), 6.39 (s, 1H), 5.06 (br s, 1H), 2.38 (s, 3H),
2
13
29.6, 129.4, 129.12 (d, J
27.4, 120.9, 120.0, 115.7 (d, J
¼ 8.069 Hz), 128.9, 128.3, 128.2, 2.31 (s, 3H) ppm; C NMR (100 MHz, CDCl ): d 190.8, 163.8,
C–F
3
1
3
¼ 21.274 Hz), 115.1, 114.9, 163.2 (d, J
¼ 249.4 Hz), 156.3, 152.3, 145.1, 143.9, 139.6,
C–F
C–F
2
14.0, 72.3 ppm; IR(KBr): n ¼ 3283, 3060, 2922, 1656, 1609, 136.6, 134.9, 134.3, 129.7, 129.1, 129.0 (d, J
¼ 7.3 Hz), 128.3,
C–F
ꢁ
1
+
1
493, 1367, 1229 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for 127.2, 126.3, 120.5, 119.9, 115.7 (d,
H 489.1609, found 489.1607.
114.9, 114.1, 72.3, 21.6, 21.3 ppm; IR(KBr): n ¼ 3343, 3051, 2918,
-(4-(4-Methylbenzoyl)-5-p-tolylfuran-2-yl)-2-phenyl-2,3-dihy- 1662, 1643, 1507, 1373, 1234, 893 cm ; HRMS (ESI-TOF) m/z:
J
C–F ¼ 22.0 Hz), 115.2,
31 2 3
C H20FN O
ꢁ
1
2
+
droquinazolin-4(1H)-one (3e). Following the general procedure, [M + H] calcd for C33
00 mg (0.274 mmol, 1.0 equiv.) of 1e, 56 mg (0.412 mmol, 1.5 2-(4-Benzoyl-5-phenylfuran-2-yl)-2-(m-tolyl)-2,3-dihy-
equiv.) of 2a, 10 mg (10 mol%) of KAuCl4 and 89 mg droquinazolin-4(1H)-one (3h). Following the general procedure,
0.549 mmol, 2.0 equiv.) of FeCl was used and the reaction time 100 mg (0.285 mmol, 1.0 equiv.) of 1h, 58 mg (0.427 mmol, 1.5
2 3
H24FN O H 517.1922, found 517.1931.
1
(
3
was 12 h. Aer ash column chromatography on silica gel equiv.) of 2a, 10 mg (10 mol%) of KAuCl4 and 92 mg
eluted with R : 0.5; hexane/ethyl acetate mixture 10/3.5), 103 mg (0.571 mmol, 2.0 equiv.) of FeCl was used and the reaction time
of 3e was obtained in 75% yield as a yellow solid. Mp: 223– was 12 h. Aer ash column chromatography on silica gel
(
f
3
ꢀ
1
2
7
7
25 C; H NMR (500 MHz, CDCl
3
): d 7.90 (d, J ¼ 7.4 Hz, 1H), (eluted with R
f
: 0.6; hexane/ethyl acetate mixture 10/3.0), 52 mg
.62–7.56 (m, 4H), 7.51 (d, J ¼ 8.0 Hz, 2H), 7.44–7.39 (m, 3H), of 3h was obtained in 37% yield as a light yellow solid. Mp: 224–
ꢀ
1
.36–7.30 (m, 1H), 7.14 (d, J ¼ 7.3 Hz, 2H), 7.06 (d, J ¼ 7.1 Hz, 226 C; H NMR (400 MHz, CDCl ): d 7.93 (dd, J ¼ 7.8, 1.4 Hz,
3
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1
7
1
H), 7.71–7.67 (m, 2H), 7.63–7.57 (m, 2H), 7.53–7.46 (m, 2H), 7.65 (m, 2H), 7.60–7.57 (m, 2H), 7.49–7.44 (m, 1H), 7.33–7.24
.37–7.23 (m, 9H), 6.94–6.89 (m, 1H), 6.76–6.72 (m, 2H), 6.33 (s, (m, 6H), 7.20 (s, 1H), 6.88–6.83 (m, 1H), 6.68 (d, J ¼ 7.9 Hz, 1H),
1
3
H), 5.08 (br s, 1H), 2.39 (s, 3H). ppm; C NMR (100 MHz, 6.52 (s, 1H), 4.75 (br s, 1H), 2.26–2.13 (m, 2H), 1.42–1.23 (m,
1
3
DMSO-d & CDCl ): d 189.1, 162.5, 153.7, 153.0, 145.2, 140.2, 8H), 0.91–0.85 (m, 3H). ppm; C NMR (100 MHz, CDCl3):
6
3
1
1
1
1
36.0, 132.0, 131.4, 127.9, 127.8, 127.7, 127.6, 126.8, 126.7, d 191.2, 165.0, 155.6, 154.7, 145.6, 137.5, 134.2, 132.9, 129.6,
26.5, 126.2, 125.8, 122.7, 119.2, 116.4, 113.4, 113.2, 111.6, 70.6, 129.2, 128.2, 127.3, 126.1, 121.0, 119.4, 114.8, 114.6, 111.1, 70.2,
9.9. ppm; IR(KBr): n ¼ 3335, 3061, 2919, 1668, 1487, 1265, 39.9, 31.5, 29.0, 23.1, 22.4, 13.9. ppm; IR(KBr): n ¼ 3301, 3060,
ꢁ
1
+
ꢁ1
148, 756 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for 2927, 1661, 1486, 1270, 1150, 756 cm ; HRMS (ESI-TOF) m/z:
+
C
32
H
24
N
2
O
3
H 485.1865, found 485.1864.
[M + H] calcd for C31
30 2 3
H N O H 479.2335, found 479.2339.
2-(4-(4-Methylbenzoyl)-5-(p-tolyl)furan-2-yl)-2-(m-tolyl)-2,3-
2-(4-Benzoyl-5-phenylfuran-2-yl)-5-methyl-2-phenyl-2,3-dihy-
dihydroquinazolin-4(1H)-one (3i). Following the general proce- droquinazolin-4(1H)-one (3l). Following the general procedure,
dure, 100 mg (0.264 mmol, 1.0 equiv.) of 1i, 54 mg (0.396 mmol, 100 mg (0.3 mmol, 1.0 equiv.) of 1a, 67 mg (0.45 mmol, 1.5
1
(
.5 equiv.) of 2a, 10 mg (10 mol%) of KAuCl
0.529 mmol, 2.0 equiv.) of FeCl was used and the reaction time 2.0 equiv.) of FeCl
was 12 h. Aer ash column chromatography on silica gel Aer ash column chromatography on silica gel (eluted with R
eluted with R : 0.6; hexane/ethyl acetate mixture 10/3.0), 56 mg 0.7; hexane/ethyl acetate mixture 10/2.5), 104 mg of 3l was ob-
of 3i was obtained in 41% yield as a light yellow solid. Mp: 204– tained in 72% yield as a yellow solid. Mp: 228–230 C; H NMR
4
and 85 mg equiv.) of 2b, 11 mg (10 mol%) of KAuCl
4
and 97 mg (0.6 mmol,
3
3
was used and the reaction time was 12 h.
f
:
(
f
ꢀ
1
ꢀ
1
2
1
7
2
06 C; H NMR (400 MHz, CDCl ): d 7.93 (dd, J ¼ 7.8, 1.3 Hz, (400 MHz, CDCl ): d 7.72–7.68 (m, 2H), 7.64–7.57 (m, 3H), 7.55–
3
3
H), 7.60 (d, J ¼ 8.1 Hz, 2H), 7.52 (d, J ¼ 8.1 Hz, 2H), 7.46 (s, 1H), 7.48 (m, 1H), 7.46–7.42 (m, 3H), 7.39–7.33 (m, 2H), 7.30–7.25
.37–7.23 (m, 4H), 7.15 (d, J ¼ 7.9 Hz, 2H), 7.08 (d, J ¼ 8.0 Hz, (m, 4H), 7.17 (t, J ¼ 7.8 Hz, 1H), 6.75 (s, 1H), 6.71 (d, J ¼ 7.5 Hz,
H), 6.94–6.89 (m, 1H), 6.72 (d, J ¼ 7.9 Hz, 1H), 6.68 (s, 1H), 6.24 1H), 6.59 (d, J ¼ 7.9 Hz, 1H), 6.21 (s, 1H), 5.03 (d, J ¼ 1.4 Hz, 1H),
1
3
(
s, 1H), 5.04 (br s, 1H), 2.38 (d, J ¼ 1.5 Hz, 6H), 2.31 (s, 3H). ppm; 2.68 (s, 3H) ppm; C NMR (100 MHz, CDCl
3
): d 191.1, 164.3,
1
3
3
C NMR (75 MHz, CDCl ): d 190.9, 163.8, 156.2, 152.7, 145.3, 156.2, 153.2, 146.5, 142.3, 140.4, 137.6, 133.1, 133.0, 129.7,
1
1
1
3
43.8, 140.4, 139.5, 138.7, 135.1, 134.3, 130.5, 129.8, 129.0, 129.6, 129.3, 129.1, 128.8, 128.3, 128.2, 127.4, 127.0, 123.6,
28.9, 128.6, 128.4, 127.6, 127.3, 126.4, 123.9, 120.5, 119.8, 120.9, 114.2, 113.8, 113.2, 72.1, 22.2 ppm; IR(KBr): n ¼ 3341,
ꢁ
1
15.2, 114.9, 114.1, 72.7, 21.6, 21.5, 21.3. ppm; IR(KBr): n ¼ 3060, 2927, 1659, 1636, 1519, 1368, 1265 cm ; HRMS (ESI-TOF)
ꢁ
1
+
448, 3034, 2919, 1663, 1498, 1271, 1155, 754 cm ; HRMS (ESI- m/z: [M + H] calcd for C H N O H 485.1859, found 485.1873.
3
2
23 2 3
+
TOF) m/z: [M + H] calcd for C H N O H 513.2178, found
2-(4-Benzoyl-5-phenylfuran-2-yl)-6-chloro-2-phenyl-2,3-dihy-
droquinazolin-4(1H)-one (3m). Following the general proce-
dure, 100 mg (0.3 mmol, 1.0 equiv.) of 1a, 76 mg (0.45 mmol, 1.5
3
4
28 2 3
513.2180.
2
-(4-(3-Methylbenzoyl)-5-(m-tolyl)furan-2-yl)-2-phenyl-2,3-
dihydroquinazolin-4(1H)-one (3j). Following the general proce- equiv.) of 2c, 11 mg (10 mol%) of KAuCl
dure, 100 mg (0.274 mmol, 1.0 equiv.) of 1j, 56 mg (0.412 mmol, 2.0 equiv.) of FeCl was used and the reaction time was 12 h.
.5 equiv.) of 2a, 10 mg (10 mol%) of KAuCl and 89 mg Aer ash column chromatography on silica gel (eluted with R
0.549 mmol, 2.0 equiv.) of FeCl was used and the reaction time 0.6; hexane/ethyl acetate mixture 10/3.0), 98 mg of 3m was ob-
4
and 97 mg (0.6 mmol,
3
1
4
f
:
(
3
ꢀ
1
was 12 h. Aer ash column chromatography on silica gel tained in 65% yield as a yellow solid. Mp: 148–150 C; H NMR
eluted with R : 0.6; hexane/ethyl acetate mixture 10/3.0), 54 mg (400 MHz, CDCl ): d 7.89 (s, 1H), 7.69 (d, J ¼ 7.4 Hz, 2H), 7.61–
(
f
3
of 3j was obtained in 39% yield as a light yellow solid. Mp: 102– 7.41 (m, 8H), 7.38–7.33 (m, 1H), 7.31–7.23 (m, 5H), 6.75–6.67
ꢀ
1
13
1
1
7
1
04 C; H NMR (400 MHz, CDCl
H), 7.61–7.56 (m, 2H), 7.51–7.42 (m, 5H), 7.40–7.28 (m, 4H), DMSO-d & CDCl ): d 190.6, 162.7, 155.6, 153.1, 144.5, 140.5,
6 3
3
): d 7.93 (dd, J ¼ 7.7, 1.3 Hz, (m, 2H), 6.48 (s, 1H), 5.16 (s, 1H), ppm; C NMR (75 MHz,
.21 (t, J ¼ 7.6 Hz, 1H), 7.17–7.12 (m, 1H), 7.09 (d, J ¼ 7.6 Hz, 137.1, 133.3, 132.6, 129.1, 128.9, 128.8, 128.7, 128.1, 127.9,
H), 6.94–6.89 (m, 1H), 6.76–6.72 (m, 2H), 6.48 (s, 1H), 5.09 127.7, 127.1, 126.9, 126.7, 123.0, 120.5, 116.2, 115.5, 113.4,
1
3
(
br s, 1H), 2.29 (s, 3H), 2.25 (s, 3H). ppm; C NMR (75 MHz, 72.1 ppm; IR(KBr): n ¼ 3283, 3060, 2924, 1658, 1610, 1486, 1265,
ꢁ
1
+
CDCl ): d 191.3, 164.0, 156.6, 152.9, 145.2, 140.4, 138.1, 137.9, 891 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for C H -
3
31 20
1
1
2
1
37.6, 134.4, 133.7, 130.1, 129.7, 129.0, 128.8, 128.4, 128.2, ClN O H 505.1313, found 505.1322.
2
3
28.1, 126.9, 126.8, 124.7, 121.0, 119.9, 115.1, 114.9, 114.0, 72.7,
2-(4-Benzoyl-5-phenylfuran-2-yl)-6-bromo-2-phenyl-2,3-dihy-
1.2, 21.1. ppm; IR(KBr): n ¼ 3318, 3056, 2920, 1657, 1485, 1270, droquinazolin-4(1H)-one (3n). Following the general procedure,
ꢁ
1
+
144, 754 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for 100 mg (0.3 mmol, 1.0 equiv.) of 1a, 86 mg (0.45 mmol, 1.5
H 499.2022, found 499.2027. equiv.) of 2d, 11 mg (10 mol%) of KAuCl and 97 mg (0.6 mmol,
-(4-Benzoyl-5-phenylfuran-2-yl)-2-hexyl-2,3-dihy- 2.0 equiv.) of FeCl was used and the reaction time was 12 h.
droquinazolin-4(1H)-one (3k). Following the general procedure, Aer ash column chromatography on silica gel (eluted with Rf:
00 mg (0.29 mmol, 1.0 equiv.) of 1k, 59 mg (0.436 mmol, 1.5 0.6; hexane/ethyl acetate mixture 10/3.0), 103 mg of 3n was
C
33
H
26
N
2
O
3
4
2
3
1
ꢀ
1
equiv.) of 2a, 11 mg (10 mol%) of KAuCl4 and 94 mg obtained in 63% yield as a yellow solid. Mp: 186–188 C; H
0.581 mmol, 2.0 equiv.) of FeCl was used and the reaction time NMR (400 MHz, CDCl
): d 8.02 (d, J ¼ 2.0 Hz, 1H), 7.73–7.67 (m,
was 12 h. Aer ash column chromatography on silica gel 2H), 7.61–7.48 (m, 5H), 7.47–7.40 (m, 4H), 7.38–7.33 (m, 1H),
eluted with R
: 0.6; hexane/ethyl acetate mixture 10/3.0), 60 mg 7.30–7.22 (m, 4H), 6.73 (s, 1H), 6.64 (d, J ¼ 8.5 Hz, 1H), 6.49 (s,
of 3k was obtained in 43% yield as a light yellow semi solid. H 1H), 5.18 (br s, 1H) ppm; C NMR (100 MHz, CDCl
NMR (400 MHz, CDCl
): d 7.87 (dd, J ¼ 7.8, 1.3 Hz, 1H), 7.68– 162.7, 156.4, 152.7, 144.2, 140.0, 137.4, 136.9, 133.1, 130.8,
(
3
3
(
f
1
13
3
): d 191.0,
3
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ꢁ
1
+
1
1
2
29.8, 129.6, 129.4, 128.9, 128.8, 128.3, 128.2, 127.4, 126.9, 1601, 1506, 1371, 1251 cm ; HRMS (ESI-TOF) m/z: [M + H]
20.9, 116.7, 114.1, 111.8, 72.7 ppm; IR(KBr): n ¼ 3325, 3064, calcd for C H N O H 515.1965, found 515.1974.
3
3
25 2 4
ꢁ1
923, 1651, 1605, 1490, 1319, 1144 cm ; HRMS (ESI-TOF) m/z:
2-(4-Benzoyl-5-phenylfuran-2-yl)-2-(4-uorophenyl)-5-
methyl-2,3-dihydroquinazolin-4(1H)-one (3r). Following the
general procedure, 100 mg (0.282 mmol, 1.0 equiv.) of 1d, 63 mg
+
[M + H] calcd for C H BrN O H 549.0808, found 549.0824.
31 20 2 3
2-(4-Benzoyl-5-phenylfuran-2-yl)-6-iodo-2-phenyl-2,3-dihy-
droquinazolin-4(1H)-one (3o). Following the general procedure, (0.423 mmol, 1.5 equiv.) of 2b, 10 mg (10 mol%) of KAuCl
00 mg (0.3 mmol, 1.0 equiv.) of 1a, 117 mg (0.45 mmol, 1.5 91 mg (0.564 mmol, 2.0 equiv.) of FeCl was used and the
equiv.) of 2e, 11 mg (10 mol%) of KAuCl and 96 mg (0.6 mmol, reaction time was 12 h. Aer ash column chromatography on
.0 equiv.) of FeCl was used and the reaction time was 12 h. silica gel (eluted with R : 0.7; hexane/ethyl acetate mixture 10/
Aer ash column chromatography on silica gel (eluted with Rf: 2.5), 98 mg of 3r was obtained in 69% yield as a yellow solid.
4
and
1
3
4
2
3
f
ꢀ
1
0
.6; hexane/ethyl acetate mixture 10/3.0), 107 mg of 3o was Mp: 170–172 C; H NMR (400 MHz, CDCl ): d 7.68 (d, J ¼
3
ꢀ
1
obtained in 60% yield as a yellow solid. Mp: 200–202 C; H 7.4 Hz, 2H), 7.63–7.49 (m, 4H), 7.38–7.25 (m, 6H), 7.21–7.07 (m,
NMR (400 MHz, CDCl
3
): d 8.21 (s, 1H), 7.70 (d, J ¼ 7.4 Hz, 2H), 3H), 6.77–6.69 (m, 2H), 6.59 (d, J ¼ 7.9 Hz, 1H), 6.38 (s, 1H), 5.02
13
7
1
.62–7.23 (m, 14H), 6.73 (s, 1H), 6.53 (d, J ¼ 8.3 Hz, 1H), 6.41 (s, (br s, 1H), 2.66 (s, 3H) ppm; C NMR (100 MHz, CDCl
3
): 191.0,
1
3
3
6 3
H), 5.16 (br s, 1H) ppm; C NMR (75 MHz, DMSO-d & CDCl
): 164.3, 163.2 (d, JC–F ¼ 250.1 Hz), 156.3, 153.0, 146.4, 142.3,
2
d 189.4, 161.5, 154.3, 152.7, 144.9, 140.3, 140.2, 136.3, 134.5, 137.5, 136.4, 133.2, 133.0, 129.6, 129.4, 129.17 (d, JC–F ¼ 8.8
1
1
1
1
31.7, 128.1, 128.0, 127.7, 127.1, 127.0, 126.9, 126.2, 125.9, Hz), 129.0, 128.36, 128.30, 127.4, 123.8, 120.9, 115.7 (d, JC–F
¼
19.5, 116.2, 115.7, 112.2, 70.9 ppm; IR(KBr): n ¼ 3324, 3062, 21.2 Hz), 114.2, 113.7, 113.2, 72.3, 22.1 ppm; IR(KBr): n ¼ 3397,
ꢁ
1
ꢁ1
646, 1602, 1489, 1318, 1146, 890 cm ; HRMS (ESI-TOF) m/z: 3062, 2923, 1661, 1601, 1504, 1360, 1224 cm ; HRMS (ESI-TOF)
+
+
[M + H] calcd for C H IN O H 597.0669, found 597.0696.
m/z: [M + H] calcd for C H FN O H 503.1765, found
32 22 2 3
3
1
20
2
3
2
-(4-Benzoyl-5-phenylfuran-2-yl)-5-methyl-2-(p-tolyl)-2,3-
dihydroquinazolin-4(1H)-one (3p). Following the general
procedure, 100 mg (0.285 mmol, 1.0 equiv.) of 1b, 64 mg 2,3-dihydroquinazolin-4(1H)-one (3s). Following the general
0.428 mmol, 1.5 equiv.) of 2b, 10 mg (10 mol%) of KAuCl and procedure, 100 mg (0.282 mmol, 1.0 equiv.) of 1d, 72 mg
2 mg (0.571 mmol, 2.0 equiv.) of FeCl was used and the (0.423 mmol, 1.5 equiv.) of 2c, 10 mg (10 mol%) of KAuCl and
503.1766.
2-(4-Benzoyl-5-phenylfuran-2-yl)-6-chloro-2-(4-uorophenyl)-
(
9
4
3
4
reaction time was 12 h. Aer ash column chromatography on 91 mg (0.564 mmol, 2.0 equiv.) of FeCl3 was used and the
silica gel (eluted with R : 0.7; hexane/ethyl acetate mixture 10/ reaction time was 12 h. Aer ash column chromatography on
f
2
.5), 103 mg of 3p was obtained in 72% yield as a yellow silica gel (eluted with R : 0.6; hexane/ethyl acetate mixture 10/
f
ꢀ
1
solid. Mp: 202–204 C; H NMR (400 MHz, CDCl
3
): d 7.69 (d, J ¼ 3.0), 93 mg of 3s was obtained in 63% yield as a yellow solid.
1
ꢀ
7
2
.3 Hz, 2H), 7.66–7.60 (m, 2H), 7.54–7.43 (m, 3H), 7.38–7.32 (m, Mp: 130–132 C; H NMR (400 MHz, CDCl
H), 7.29–7.21 (m, 5H), 7.18–7.13 (m, 1H), 6.73 (s, 1H), 6.69 (d, J 2.2 Hz, 1H), 7.68 (d, J ¼ 7.4 Hz, 2H), 7.59–7.47 (m, 5H), 7.37–7.22
7.4 Hz, 1H), 6.58 (d, J ¼ 7.9 Hz, 1H), 6.29 (s, 1H), 5.03 (br s, (m, 6H), 7.15–7.06 (m, 2H), 6.76–6.67 (m, 3H), 5.19 (br s,
3
): d 7.85 (d, J ¼
¼
1
3
13
3
1
H), 2.67 (s, 3H), 2.38 (s, 3H) ppm; C NMR (100 MHz, CDCl
3
): 1H) ppm; C NMR (100 MHz, CDCl
3
): d 190.9, 163.3 (d, JC–F
¼
d 191.1, 164.4, 156.1, 153.4, 146.6, 142.2, 139.6, 137.67, 137.61, 250.8 Hz), 162.8, 156.5, 152.4, 143.5, 137.3, 136.0, 134.3, 133.1,
2
1
1
33.0, 132.9, 129.6, 129.4, 129.2, 129.1, 128.3, 128.2, 127.4, 129.6, 129.5, 129.13 (d, JC–F ¼ 8.1 Hz), 128.8, 128.4, 128.3,
1
26.8, 123.5, 120.8, 114.0, 113.7, 113.2, 71.9, 22.1, 21.1 ppm; 127.9, 127.5, 125.2, 120.9, 116.5, 116.4, 115.8 (d, J
¼ 22.0
C–F
IR(KBr): n ¼ 3321, 3037, 2919, 1652, 1601, 1507, 1373, Hz), 114.2, 72.3 ppm; IR(KBr): n ¼ 3279, 3062, 2923, 1660, 1607,
ꢁ1
+
ꢁ1
+
1
C
269 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for 1486, 1347, 1231 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for
H 499.2016, found 499.2021. 19ClFN H 523.1219, found 523.1230.
-(4-Benzoyl-5-phenylfuran-2-yl)-2-(4-methoxyphenyl)-5- 2-(4-Benzoyl-5-phenylfuran-2-yl)-6-bromo-2-(4-uorophenyl)-
33
H
25
N
2
O
3
C
31
H
2 3
O
2
methyl-2,3-dihydroquinazolin-4(1H)-one (3q). Following the 2,3-dihydroquinazolin-4(1H)-one (3t). Following the general
general procedure, 100 mg (0.273 mmol, 1.0 equiv.) of 1c, 61 mg procedure, 100 mg (0.282 mmol, 1.0 equiv.) of 1d, 91 mg
(
0.409 mmol, 1.5 equiv.) of 2b, 10 mg (10 mol%) of KAuCl and (0.423 mmol, 1.5 equiv.) of 2d, 10 mg (10 mol%) of KAuCl and
4
4
88 mg (0.546 mmol, 2.0 equiv.) of FeCl3 was used and the 91 mg (0.564 mmol, 2.0 equiv.) of FeCl3 was used and the
reaction time was 12 h. Aer ash column chromatography on reaction time was 12 h. Aer ash column chromatography on
silica gel (eluted with R : 0.7; hexane/ethyl acetate mixture 10/ silica gel (eluted with R : 0.6; hexane/ethyl acetate mixture 10/
.5), 98 mg of 3q was obtained in 70% yield as a yellow solid. 3.0), 98 mg of 3t was obtained in 61% yield as a yellow solid.
f
f
2
ꢀ
1
ꢀ
1
Mp: 223–225 C; H NMR (400 MHz, CDCl
3
): d 7.69 (d, J ¼ Mp: 198–200 C; H NMR (400 MHz, CDCl
.3 Hz, 2H), 7.66–7.61 (m, 2H), 7.54–7.46 (m, 3H), 7.39–7.33 (m, 2.0 Hz, 1H), 7.72–7.66 (m, 2H), 7.59–7.49 (m, 4H), 7.46–7.41 (m,
H), 7.30–7.25 (m, 3H), 7.19–7.13 (m, 1H), 6.92 (d, J ¼ 8.8 Hz, 1H), 7.38–7.23 (m, 7H), 7.15–7.09 (m, 1H), 6.74 (s, 1H), 6.65 (d, J
3
): d 8.02 (d, J ¼
7
2
2
6
1
3
H), 6.73 (s, 1H), 6.69 (d, J ¼ 7.4 Hz, 1H), 6.58 (d, J ¼ 7.8 Hz, 1H), ¼ 8.5 Hz, 1H), 6.56 (s, 1H), 5.13 (br s, 1H) ppm; C NMR (100
1
3
3
.25 (s, 1H), 5.01 (br s, 1H), 3.83 (s, 3H), 2.67 (s, 3H) ppm;
C
MHz, CDCl ): d 190.9, 163.3 (d, J
): d 191.1, 164.4, 160.4, 156.1, 153.4, 152.4, 144.0, 137.3, 137.0, 135.9, 133.1, 130.9, 129.6, 129.5,
¼ 250.1 Hz), 162.7, 156.5,
3
C–F
NMR (100 MHz, CDCl
3
2
1
1
1
46.6, 142.2, 137.6, 133.1, 132.9, 132.5, 129.6, 129.3, 129.1, 129.12 (d,
J
C–F ¼ 8.8 Hz), 128.8, 128.4, 128.3, 127.5, 120.9,
1
28.4, 128.3, 128.2, 127.4, 123.6, 120.8, 114.1, 113.9, 113.7, 116.820, 116.820, 115.8 (d, JC–F ¼ 22.0 Hz), 112.1, 72.3 ppm;
13.2, 71.8, 55.3, 22.2 ppm; IR(KBr): n ¼ 3326, 3034, 2920, 1652, IR(KBr): n ¼ 3319, 3064, 1654, 1604, 1499, 1319, 1230,
35688 | RSC Adv., 2020, 10, 35681–35691
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ꢁ1
+
+
1
144 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for C31
H
19
-
(ESI-TOF) m/z: [M + H] calcd for C35
H
29
N
2
O
3
H 527.2329, found
BrFN O H 567.0714, found, 567.0732.
527.2346.
2
3
2
-(4-Benzoyl-5-phenylfuran-2-yl)-2-(4-uorophenyl)-6-iodo-
,3-dihydroquinazolin-4(1H)-one (3u). Following the general uoromethyl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one
procedure, 100 mg (0.282 mmol, 1.0 equiv.) of 1d, 111 mg (3x). Following the general procedure, 100 mg (0.3 mmol, 1.0
0.423 mmol, 1.5 equiv.) of 2e, 10 mg (10 mol%) of KAuCl and equiv.) of 1a, 112 mg (0.45 mmol, 1.5 equiv.) of 2f, 10 mg
1 mg (0.564 mmol, 2.0 equiv.) of FeCl was used and the (10 mol%) of KAuCl and 97 mg (0.6 mmol, 2.0 equiv.) of FeCl
reaction time was 12 h. Aer ash column chromatography on was used and the reaction time was 12 h. Aer ash column
silica gel (eluted with R : 0.6; hexane/ethyl acetate mixture 10/ chromatography on silica gel (eluted with R : 0.6; hexane/ethyl
.0), 107 mg of 3u was obtained in 62% yield as a yellow acetate mixture 10/3.0), 106 mg of 3x was obtained in 58%
2-(4-Benzoyl-5-phenylfuran-2-yl)-2,7-diphenyl-5-(tri-
2
(
9
4
3
4
3
f
f
3
ꢀ
1
ꢀ
1
solid. Mp: 194–196 C; H NMR (400 MHz, CDCl ): d 8.20 (d, J ¼ yield as a yellow solid. Mp: 140–142 C; H NMR (500 MHz,
3
1
.5 Hz, 1H), 7.72–7.67 (m, 2H), 7.62–7.49 (m, 6H), 7.40–7.33 (m, CDCl ): d, 8.03–7.96 (m, 2H), 7.79–7.73 (m, 2H), 7.64–7.57 (m,
3
2
¼
H), 7.30–7.24 (m, 4H), 7.16–7.08 (m, 1H), 6.74 (s, 1H), 6.54 (d, J 4H), 7.54–7.45 (m, 7H), 7.40–7.35 (m, 2H), 7.29–7.25 (m, 5H),
8.4 Hz, 1H), 6.49 (s, 1H), 5.13 (br s, 1H) ppm; C NMR (75 6.83 (s, 1H), 6.39 (s, 1H) ppm; C NMR (100 MHz, CDCl ):
3
1
3
13
3
2
MHz, DMSO-d
6
& CDCl
3
): d 188.8, 160.95, 160.93 (d,
J
C–F
¼
d 190.9, 161.5, 160.7, 157.7, 156.7, 152.2, 139.7 (q, JC–F ¼ 33.7
2
1
1
47.0 Hz), 153.8, 152.1, 144.4, 140.0, 136.0, 135.8, 134.0, 131.4, Hz), 139.3, 137.4, 136.8, 133.1, 130.7, 129.8, 129.5, 129.4, 128.9,
2
1
27.7, 127.6, 127.5, 126.7 (d,
J
C–F ¼ 11.0 Hz), 125.8, 119.1, 128.8, 128.3, 128.2, 127.4, 127.2, 126.6, 122.3 (q, JC–F ¼ 272.1
1
15.9, 115.3, 113.4 (d, J ¼ 22.0 Hz), 111.7, 70.0 ppm; IR(KBr): Hz), 120.9, 114.3, 110.78, 110.73, 104.4, 71.2 ppm; IR(KBr): n ¼
C–F
ꢁ
1
ꢁ1
n ¼ 3319, 3062, 1650, 1601, 1494, 1319, 1231, 1153 cm ; HRMS 3196, 3063, 2922, 1677, 1579, 1447, 1263, 1156 cm ; HRMS
+
+
(ESI-TOF) m/z: [M + H] calcd for C H FIN O H 615.0575, (ESI-TOF) m/z: [M + H] calcd for C H F N O H 616.1842,
31 19 2 3 37 23 3 3 3
found, 615.0602.
found 616.1869.
Dimethyl(2-methyl-5-(4-oxo-2-phenyl-1,2,3,4-
phenyl-2,3-dihydroquinazolin-4(1H)-one (3v). Following the tetrahydroquinazolin-2-yl)furan-3-yl)phosphonate
general procedure, 100 mg (0.274 mmol, 1.0 equiv.) of 1e, 62 mg Following the general procedure, 100 mg (0.359 mmol, 1.0
0.412 mmol, 1.5 equiv.) of 2b, 10 mg (10 mol%) of KAuCl and equiv.) of 1l, 73 mg (0.539 mmol, 1.5 equiv.) of 2a, 14 mg
9 mg (0.549 mmol, 2.0 equiv.) of FeCl3 was used and the (10 mol%) of KAuCl and 116 mg (0.719 mmol, 2.0 equiv.) of
5-Methyl-2-(4-(4-methylbenzoyl)-5-p-tolylfuran-2-yl)-2-
(3y).
(
4
8
4
reaction time was 12 h. Aer ash column chromatography on FeCl3 was used and the reaction time was 12 h. Aer ash
silica gel (eluted with R : 0.7; hexane/ethyl acetate mixture 10/ column chromatography on silica gel (eluted with R : 0.8;
f
f
2
.5), 99 mg of 3v was obtained in 70% yield as a yellow solid. hexane/ethyl acetate mixture 10/7.0), 101 mg of 3y was obtained
ꢀ
1
ꢀ
1
Mp: 180–182 C; H NMR (400 MHz, CDCl
6
2
3
): d 7.64–7.52 (m, in 68% yield as a light yellow solid. Mp: 226–228 C; H NMR
H), 7.46–7.40 (m, 3H), 7.19–7.13 (m, 3H), 7.08 (d, J ¼ 8.0 Hz, (300 MHz, CDCl ): d 7.88 (d, J ¼ 7.7 Hz, 1H), 7.50–7.30 (m, 6H),
H), 6.73–6.66 (m, 2H), 6.58 (d, J ¼ 7.9 Hz, 1H), 6.24 (s, 1H), 5.04 6.87 (t, J ¼ 7.7 Hz, 1H), 6.71 (d, J ¼ 7.9 Hz, 1H), 6.50 (d, J ¼
3
1
3
(br s, 1H), 2.68 (s, 3H), 2.39 (s, 3H), 2.31 (s, 3H) ppm; C NMR 3.3 Hz, 1H), 6.27 (s, 1H), 4.99 (br s, 1H), 3.75–3.63 (m, 6H), 2.45
1
3
(
100 MHz, CDCl ): d 190.8, 164.3, 156.2, 152.6, 146.6, 143.8, (d, J ¼ 1.9 Hz, 3H). ppm; C NMR (75 MHz, DMSO-d & CDCl ):
3
6
3
2
1
1
2
1
42.3, 140.6, 139.4, 135.2, 133.0, 129.7, 129.6, 129.0, 128.9, d 162.2, 158.8, 158.4, 153.0 (d, J
28.7, 127.2, 127.0, 126.5, 123.6, 120.4, 114.3, 113.7, 113.2, 72.1, 131.9, 127.0, 126.5, 125.7, 125.5, 116.1, 113.2, 112.9, 110.2(d,
¼ 14.8 Hz), 144.9, 140.4,
C,P
2
2
2.2, 21.6, 21.3 ppm; IR(KBr): n ¼ 3326, 3056, 2922, 1652, 1602,
J
C,P ¼ 11.5 Hz), 106.0, 103.2, 70.2, 50.6 (d,
J
C,P ¼ 4.9 Hz),
& DMSO-d ) 21.287 (m);
IR(KBr): n ¼ 3443, 3252, 2953, 1659, 1521, 1242, 1018, 830 cm
ꢁ
1
+
31
499, 1368, 1269 cm ; HRMS (ESI-TOF) m/z: [M + H] calcd for 11.9. ppm; P NMR (162 MHz, CDCl
H 513.2172, found 513.2177.
21 2 5
-Methyl-2-(4-(4-methylbenzoyl)-5-p-tolylfuran-2-yl)-2-p-tolyl- HRMS (ESI-TOF) m/z: [M + H] calcd for C21H N O PH
3
6
ꢁ1
C
34
H
5
27
N
2
O
3
;
+
2
,3-dihydroquinazolin-4(1H)-one (3w). Following the general 413.1266, found 413.1266.
0
procedure, 100 mg (0.264 mmol, 1.0 equiv.) of 1f, 60 mg
N -((4-Benzoyl-5-phenylfuran-2-yl)(phenyl)methylene)-2-
(
0.396 mmol, 1.5 equiv.) of 2b, 10 mg (10 mol%) of KAuCl and (prop-2-yn-1-yloxy)benzohydrazide (5). Following the general
4
8
5 mg (0.529 mmol, 2.0 equiv.) of FeCl3 was used and the procedure, 100 mg (0.297 mmol, 1.0 equiv.) of 1a, 85 mg
reaction time was 12 h. Aer ash column chromatography on (0.446 mmol, 1.5 equiv.) of 7, 10 mg (10 mol%) of KAuCl and
silica gel (eluted with R : 0.7; hexane/ethyl acetate mixture 10/ 96 mg (0.595 mmol, 2.0 equiv.) of FeCl was used and the
.5), 95 mg of 3w was obtained in 68% yield as a yellow solid. reaction time was 12 h. Aer ash column chromatography on
4
f
3
2
ꢀ
1
Mp: 228–230 C; H NMR (400 MHz, CDCl
8
3
): d 7.60 (d, J ¼ silica gel (eluted with R
f
: 0.6; hexane/ethyl acetate mixture 10/
.1 Hz, 2H), 7.54 (d, J ¼ 8.3 Hz, 2H), 7.44 (d, J ¼ 8.3 Hz, 2H), 7.21 3.0), 97 mg of 8 was obtained in 62% yield as a yellow solid.
ꢀ
1
(
d, J ¼ 7.9 Hz, 2H), 7.19–7.12 (m, 3H), 7.08 (d, J ¼ 8.0 Hz, 2H), Mp: 73–75 C; H NMR (400 MHz, CDCl ): d 10.81 (s, 1H), 8.34
3
6
5
3
1
1
1
3
.71–6.67 (m, 2H), 6.56 (d, J ¼ 7.9 Hz, 1H), 6.24–6.17 (m, 1H), (dd, J ¼ 7.8 Hz, 1.7 Hz, 1H), 7.83–7.78 (m, 2H), 7.75–7.70 (m,
.04–4.98 (br s, 1H), 2.68 (s, 3H), 2.38 (d, J ¼ 4.8 Hz, 6H), 2.31 (s, 2H), 7.69–7.62 (m, 3H), 7.55–7.41 (m, 4H), 7.39–7.33 (m, 2H),
1
3
H) ppm; C NMR (100 MHz, CDCl
3
): d 190.9, 164.4, 156.1, 7.30–7.26 (m, 3H), 7.18–7.11 (m, 1H), 7.01 (d, J ¼ 8.3 Hz, 1H),
52.8, 146.7, 143.7, 142.2, 139.6, 139.3, 137.7, 135.2, 133.0, 6.72 (s, 1H), 4.18 (d, J ¼ 2.2 Hz, 2H), 2.50 (t, J ¼ 2.2 Hz, 1H), ppm;
1
3
29.7, 129.3, 129.0, 128.9, 127.2, 126.9, 126.5, 123.5, 120.4,
3
C NMR (100 MHz, CDCl ): d 191.4, 161.2, 157.1, 154.9, 149.8,
14.1, 113.7, 113.2, 71.9, 22.1, 21.6, 21.3, 21.0 ppm; IR(KBr): n ¼ 145.0, 137.4, 133.2, 133.0, 131.4, 130.2, 129.69, 129.62, 129.4,
ꢁ
1
328, 3040, 2922, 1648, 1602, 1501, 1368, 1269, 891 cm ; HRMS 128.9, 128.6, 128.3, 128.2, 127.9, 122.5, 122.4, 120.8, 116.9,
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1
2
12.7, 55.8. ppm; IR(KBr): n ¼ 3357, 3297, 3200, 3058, 2923,
T. R. Mitchell, M. J. Novak and R. R. Sinden, Escherichia
coli, J. Med. Chem., 2010, 53, 3558; (c) L. Gao, Z. Xu, Y. Rao,
Y.-T. Lu, Y.-T. Hu, H. Yu, Y.-H. Xu, Q.-Q. Song, J.-M. Ye and
Z.-S. Huang, Eur. J. Med. Chem., 2018, 147, 90; (d)
M. G. Nathalie, D. C. B. Craig and K. L. Evelyn, J. Neurosci.,
2012, 32, 5804; (e) M. J. Hour, L. J. Huang, S. C. Kuo,
Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel and K. H. Lee, J.
Med. Chem., 2000, 43, 4479; (f) G. M. Chinigo, M. Paige,
S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz,
W. Minor and M. L. Brown, J. Med. Chem., 2008, 51, 4620.
8 (a) E. Shirakawa, D. Ikeda, S. Masui, M. Yoshida and
T. Hayashi, J. Am. Chem. Soc., 2012, 134, 272; (b) L. Yifan
and W. J ´e r ˆo me, Beilstein J. Org. Chem., 2013, 9, 1763; (c)
D.-S. Kim, W.-J. Park and C.-H. Jun, Chem. Rev., 2017, 117,
8977.
ꢁ
1
853, 1655, 1598, 1476, 1231, 1012, 752 cm ; HRMS (ESI-TOF)
+
m/z: [M + H] calcd for C H N O H 525.1814, found 525.1808.
3
4
24 2 4
ꢁ1
Crystal data 5. C H N O (M ¼1066.17 g mol ): triclinic,
7
0
53 4 9
ꢀ
ꢁ
ꢁ
space group P1 (no. 2), a ¼ 9.1182(6) A, b ¼ 13.8291(10) A, c ¼
ꢁ
ꢀ
ꢀ
ꢀ
2
3.4126(16) A, a ¼ 103.581(1) , b ¼ 91.205(2) , g ¼ 98.758(2) , V
3
ꢁ1
ꢁ
¼
2831.3(3) A , Z ¼ 2, T ¼ 294.15 K, m(Mo Ka) ¼ 0.084 mm
,
ꢁ3
ꢀ
D
calc ¼ 1.2505 g cm , 35 814 reections measured (1.8 # 2Q #
ꢀ
5
0 ), 9961 unique (Rint ¼ 0.0944, Rsigma ¼ 0.1499) which were
used in all calculations. The nal R was 0.1271 (I > 2s(I)) and
1
wR was 0.3437 (all data). CCDC 1898773.
2
Conflicts of interest
There are no conicts to declare.
9
(a) D. Sudarshan, S. Sougata, J. Sourav, V. Z. Grigory,
M. Adinath and H. Alakananda, Eur. J. Org. Chem., 2017,
Acknowledgements
4955; (b) A. Dutta, D. Krishnaiah, A. Kumar, S. J. Prakash
We thank Department of Science and Technology (DST) India
grant no: DST-SB/EMEQ-257/2014 and CSIR, New Delhi for
and D. Sarma, Tetrahedron Lett., 2020, 61, 151587; (c)
Q. Liu, Y. Sui, Y. Zhang, K. Zhang, Y. Chen and H. Zhou,
Synlett, 2020, 31, 275; (d) T. Tamoradi, S. M. Mousavi and
M. Mohammadi, New J. Chem., 2020, 44, 3012; (e)
H. Kothayer, M. S. Ibrahim, K. S. Moustafa, R. Samar and
S. M. Shireen, Drug Dev. Res., 2019, 80, 343; (f) J. Mou,
N. Chen, Y. Zhao, H. Qi, S. Meng, R. Xiang and D. Pei,
Front. Chem., 2020, 8, 239; (g) S. J. Wu, Z. Q. Zhao,
G. J. Shuo, H. B. Chen and G. F. Chen, Res. Chem.
Intermed., 2019, 45, 2327; (h) A. Dutta, D. Krishnaiah,
B. Ankur, A. Kumar and D. Sarma, Tetrahedron Lett., 2019,

nancial support. We are thankful to Director Dr S. Chan-
drasekhar CSIR-IICT for his support. We thank Dr S. Suresh for
his suggestions on this work. We acknowledge our colleagues
from CSIR-IICT Dr K. Srinivas and Dr Rajesh for their
encouragement. V. K thanks to UGC-SRF, K. S thanks to Dr Ch.
Raji Reddy and CSIR grant HCP-0011. P. B. K and C. E. R thanks
to DST for Inspire fellowship and also thanks to AcSIR, manu-
script communication number:IICT/pubs.2019/176.
6
0, 1614; (i) G. Yashwantrao, P. J. Valmik, K. Rajpratap and
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