Full text of DOI:10.1002/bkcs.11545

Note
DOI: 10.1002/bkcs.11545
BULLETIN OF THE
J. M. Yoo et al.
KOREAN CHEMICAL SOCIETY
Copper-catalyzed C N Coupling and Cyclization of
2
-(2-Bromophenyl)-1H-indoles with Primary Amides Leading
to Indolo[1,2-c]quinazolines
*
Jae Myeong Yoo, Pham Duy Quang Dao, and Chan Sik Cho
Department of Applied Chemistry, Kyungpook National University, Daegu 41566, Republic of Korea.
E-mail: cscho@knu.ac.kr
*
Received May 15, 2018, Accepted July 3, 2018
Keywords: Copper catalyst, Cyclization, Indolo[1,2-c]quinazolines, Primary amides, Heterocycles
1
4
It is well-known that indole-fused quinazolines, indolo
1,2-c]quinazolines exhibit biological activities such as anti-
leading to 3-alkylideneisoindolin-1-ones. The molar ratio
of [2a]/[1a] affected the yield of 3a and the yield increased
with the increase of the molar ratio up to 2.0 along with
complete conversion of 1a (entry 3). Lower reaction tem-
perature resulted in a decreased yield of 3a (entry 4). The
reaction proceeded using other amino acids such as glycine,
L-phenylalanine, N,N-dimethylglycine, and 4-hydroxy-L-
proline in place of L-proline, but the yield of 3a was gener-
ally lower than that by the use of L-proline except for
4-hydroxy-L-proline, which exhibited similar activity as L-
proline (entries 5–8).
[
1
,2
bacterial and antifungal properties (Scheme 1). Since the
synthesis of indolo[1,2-c]quinazolines by thermal cycliza-
tion of 2-(2-aminophenyl)indoles with acyl cyanides fol-
lowed by HCl treatment, many synthetic methods for such
3
,4
a hybrid scaffold are well documented. Several groups
have shown that indolo[1,2-c]quinazolines can be formed
by condensation of 2-(2-aminophenyl)indoles with aromatic
aldehydes and subsequent treatment with powdered
1
,2,5
KMnO for oxidative cyclization.
Such a hybrid scaf-
4
fold formation was also exemplified by palladium-catalyzed
cyclocarbonylation of bis(o-trifluoroacetamidophenyl)-
acetylene with aryl or vinyl halides and triflates and
Among bases examined under the employed conditions,
Cs
CO
2 3
was shown to be the base of choice (entries 3 and
CO , copper cata-
6
9–11). When used with L-proline and Cs
2
3
cyclization of 1-(N-arylimino)indoles formed by addition-
lysts such as CuCl, CuBr, and copper powder showed
lower catalytic activity than CuI (entries 12–14). As a
result, even though the exact roles of copper catalysts,
ligands and bases are still obscure, the best result in terms
of both product yield and complete conversion of 1a is
obtained using the standard set of reaction conditions
shown in entry 3 of Table 1.
elimination between indoles and N-aryltrifluoroacetimidoyl
7
chlorides. It is also reported that 2-(2-halophenyl)indoles
are coupled and cyclized with (aryl)methaneamines, ami-
dine hydrochlorides, and amino acids in the presence of a
8–10
copper catalyst to give indolo[1,2-c]quinazolines.
Wang
et al. recently reported on synthesis of indolo[1,2-c]quina-
zolines from N-{2-[(2-aminophenyl)ethynyl]phenyl}amides
Based on optimized reaction conditions, various
2-(2-bromophenyl)-1H-indoles 1 were subjected to the
reaction with primary amides 2 in order to investigate the
reaction scope, and several representative results are sum-
marized in Table 2. 2-(2-Bromophenyl)-1H-indole (1a) was
coupled and cyclized with aliphatic, aromatic and hetero-
aromatic primary amides (2b-e) to give the corresponding
indolo[1,2-c]quinazolines (3b-e) in the range of 40–59%
isolated yields. However, unlike the reaction with formam-
ide (2a), higher reaction temperature was needed for the
reaction with 2b-e to get similar yields of 3b-e as that of
3a. For example, treatment of 1a with 2d under the
11
by ZnBr -promoted domino hydroamination-cyclization.
2
During the course of our continuing studies directed
1
2
towards cyclization reactions, we have identified several
13
new synthetic methods for N-fused hybrid scaffolds.
Under these circumstances, this report describes copper-
catalyzed coupling and cyclization of 2-(2-bromophenyl)-
1H-indoles with primary amides leading to indole-fused
quinazolines, indolo[1,2-c]quinazolines.
Treatment of 2-(2-bromophenyl)-1H-indole (1a) with an
ꢀ
equimolar amount of formamide (2a) in DMF at 130 C for
24 h in the presence of a catalytic amount of CuI (10 mol
ꢀ
%
) along with Cs CO afforded indolo[1,2-c]quinazoline
employed conditions (130 C) afforded in only 21% isolated
2
3
(
3a) in 10% isolated yield with several unidentifiable prod-
yield of 3d, giving 52% yield of 3d at higher reaction tem-
perature (150 C). The reaction of 2-(2-bromophenyl)-1H-
ꢀ
ucts (Table 1, entry 1). Higher reaction rate and yield were
observed with further addition of L-proline as a ligand
indoles (1b-d) having electron-donating and –withdrawing
2
3
(entry 2). It is known that the catalytic system of CuI com-
substituents (R and R ) on indole moiety with primary
amides (2a and 2d) also afforded the corresponding
coupled and cyclized indolo[1,2-c]quinazolines 3f-j and the
bined with L-proline effectively catalyzes coupling and
cyclization of 2-bromobenzamides with terminal alkynes
Bull. Korean Chem. Soc. 2018
© 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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BULLETIN OF THE
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KOREAN CHEMICAL SOCIETY
In summary, it has been shown that 2-(2-bromophenyl)-
1H-indoles react with primary amides in the presence of
CuI and L-proline along with a base to give indolo[1,2-c]
quinazolines via C N coupling and cyclization process.
The present reaction provides a new method for the synthe-
sis of indole-fused quinazolines, indolo[1,2-c]quinazolines
from readily available starting compounds. Further studies
on the synthesis of N-fused hybrid scaffolds using copper-
catalyzed coupling and cyclization protocol are underway.
Scheme 1. Indolo[1,2-c]quinazoline.
product yield was not affected by the position and elec-
tronic nature of the substituent on 1b-d. With
2
-(2-bromophenyl)-1H-indoles 1e-g having straight alkyl
1
chains at position 3 (R ) of indole moiety, the correspond-
ing coupled and cyclized indolo[1,2-c]quinazolines 3k-o
were also invariably formed irrespective of the chain length
of 1e-g. As is the case for the reaction with 1e-g, the cou-
pling and cyclization also similarly proceeded with
Experimental
1
13
General. H (400 and 500 MHz) and C NMR (100 and
25 MHz) spectra were recorded on Bruker Avance
1
2
-(2-bromophenyl)-1H-indole 1h having branched alkyl
(Billerica, MA, USA) spectrometers using TMS as an inter-
nal standard. Melting points were determined on a Stanford
Research Inc. (Sunnyvale, CA, USA). MPA100 automated
melting point apparatus. High-resolution mass data were
recorded using electronic ionization (HRMS-EI, magnetic
sector-electric sector double focusing mass analyzer) at the
Korea Basic Science Center (Daegu, Korea). The isolation
of pure products was carried out via thin layer (silica gel
60 GF254, Merck, Darmstadt, Germany) chromatography.
The starting 2-(2-bromophenyl)-1H-indoles were prepared
from the corresponding 1-(2-bromophenyl)alkanones and
1
chain at position 3 (R ).
The present reaction seems to proceed via an initial for-
mation of C N coupled intermediate 4 by copper-catalyzed
Ullmann-type coupling between 1a and 2, which triggers
cyclization and dehydration to give 2-(2-bromophenyl)-1H-
1
5,16
indole 3 (Scheme 2).
It is reported that N-substituted o-
bromobenzamides and 2-(2-bromoaryl)-1H-imidazoles are
found to be coupled and cyclized with primary amides in
the presence of CuI to give quinazolinones and imidazo
17,18
[1,2-c]quinazolines.
We confirmed in a separate experi-
19,20
ment that C N coupled intermediate 6 is formed in 56%
yield from 2-(2-bromophenyl)-1-methyl-1H-indole (5) and
arylhydrazines according to literature procedures.
Com-
mercially available organic and inorganic compounds were
2d under the employed conditions (Scheme 3).
used without further purification.
a
Table 1. Optimization of conditions for the reaction of 1a with 2a.
Entry
[2a]/[1a]
Cu cat.
Ligand
Base
Yield (%)
1
2
3
1.0
1.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
2.0
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuI
CuCl
CuBr
Cu powder
—
Cs CO3
Cs CO
2 3
10
27
59
36
36
43
15
58
40
49
35
12
43
6
2
L-proline
L-proline
L-proline
Glycine
L-phenylalanine
N,N-Dimethylglycine
4-hydroxy-L-proline
L-proline
L-proline
L-proline
Cs CO3
2
b
4
Cs CO3
2
5
6
7
8
9
Cs
Cs
2
2
CO
CO
3
3
Cs CO3
2
Cs
2
CO
CO
3
K
2
3
t
10
11
12
13
14
a
NaO Bu
PO
CO
Cs CO3
K
3
4
L-proline
L-proline
L-proline
Cs
2
3
2
2 3
Cs CO
Except as noted, all reactions were carried out with 1a (0.5 mmol), Cu catalyst (0.05 mmol), L-proline (0.15 mmol), base (1.5 mmol), and DMF
5 mL) at 130 C for 24 h.
ꢀ
(
b
ꢀ
At 100 C.
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BULLETIN OF THE
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KOREAN CHEMICAL SOCIETY
Table 2. Copper-catalyzed coupling and cyclization of 1 with
a
primary amides 2 leading to indolo[1,2-c]quinazolines 3.
Scheme 3. Experiment for the formation of C N coupled
intermediate.
10
3
g and 3j, all new products were characterized spectro-
scopically as shown below.
1
0-Methylindolo[1,2-c]quinazoline (3f).
Solid; mp
ꢀ
1
215–216 C (from CH Cl -hexane); H NMR (400 MHz,
2
2
CDCl ) δ 2.47 (s, 3H), 6.97 (s, 1H), 7.15 (dd, J = 1.2 and
3
8
.4 Hz, 1H), 7.40–7.48 (m, 2H), 7.52 (s, 1H), 7.70–7.73 (m,
H), 7.75 (d, J = 8.4 Hz, 1H), 7.95–7.97 (m, 1H), 8.90 (s, 1H);
1
13
C NMR (100 MHz, CDCl ) δ 21.98, 94.49, 109.67, 120.78,
3
121.60, 123.29, 124.08, 127.76, 128.30, 128.88, 129.16,
1
30.20, 133.20, 133.98, 137.33, 139.67; HRMS (EI) anal.
+
calcd for C H N (M ): 232.1000. Found: 232.1003.
16 12 2
8
1
-Methylindolo[1,2-c]quinazoline (3h).
Solid; mp
ꢀ
1
70–171 C (from CH Cl -hexane); H NMR (500 MHz,
2
2
CDCl ) δ 2.92 (s, 3H), 7.17–7.18 (m, 2H), 7.33 (t,
3
J = 7.5 Hz, 1H), 7.48–7.51 (m, 1H), 7.52–7.56 (m, 1H),
7
1
.69 (d, J = 8.0 Hz, 1H), 7.78 (dd, J = 1.0 and 7.8 Hz,
13
H), 8.05 (dd, J = 1.0 and 7.5 Hz, 1H), 9.38 (s, 1H);
C
NMR (125 MHz, CDCl ) δ 21.75, 95.77, 118.97, 121.63,
3
1
1
22.88, 123.19, 123.97, 125.51, 127.73, 127.94, 129.21,
29.85, 130.44, 133.35, 138.94, 139.53; HRMS (EI) anal.
+
calcd for C H N (M ): 232.1000. Found: 232.1000.
16 12 2
1
0-Chloroindolo[1,2-c]quinazoline (3i).
Solid; mp
ꢀ
1
2
30–231 C (from CH Cl -hexane); H NMR (400 MHz,
2
2
a
CDCl ) δ 7.00 (s, 1H), 7.29 (dd, J = 2.0 and 8.6 Hz, 1H),
3
All reactions were carried out with 1 (0.5 mmol), 2 (1 mmol), CuI
7
.44–7.53 (m, 2H), 7.72–7.76 (m, 2H), 7.80 (d, J = 8.8 Hz,
(
0.05 mmol), L-proline (0.15 mmol), Cs
2 3
CO (1.5 mmol), and DMF
13
ꢀ
ꢀ
1H), 7.97–7.99 (m, 1H), 8.91 (s, 1H);
C NMR
(5 mL) at 150 C (130 C with 2a) for 24 h.
(
100 MHz, CDCl ) δ 94.32, 111.08, 120.56, 121.14,
3
General Procedure for CuI-catalyzed Coupling and
Cyclization of 2-(2-Bromophenyl)-1H-Indoles 1 with
Primary Amides 2. To a 25 mL round-bottom flask was
added 1 (0.5 mmol), 2 (1.0 mmol), CuI (0.010 g,
122.75, 123.50, 128.15, 128.52, 128.89, 129.77, 129.99,
130.97, 134.41, 136.90, 139.66; HRMS (EI) anal. calcd for
+
C H ClN (M ): 252.0454. Found: 252.0456.
15
9
2
1
1
2-Methylindolo[1,2-c]quinazoline (3k).
Solid; mp
0
.05 mmol), L-proline (0.018 g, 0.15 mmol), Cs CO3
1
2
ꢀ
66–168 C (from CH Cl -hexane); H NMR (500 MHz,
2
2
(
0.489 g, 1.5 mmol), and DMF (5 mL). The mixture was
CDCl ) δ 2.60 (s, 3H), 7.29–7.32 (m,1H), 7.34–7.42 (m,
ꢀ
3
stirred at 130–150 C for 24 h. The mixture was then cooled
to room temperature and filtered through a short silica gel
column (CH Cl -MeOH) to remove inorganic salts.
3
8
H), 7.65–7.68 (m, 2H), 7.74 (d, J = 8.0 Hz, 1H),
.03–8.07 (m, 1H), 8.74 (s, 1H); C NMR (125 MHz,
13
2
2
CDCl ) δ 10.78, 106.21, 109.65, 118.94, 122.54, 123.18,
3
Removal of the solvent left a crude mixture, which was
separated by TLC [silica gel 60 GF254 (Merck), CH Cl -
1
1
23.69, 124.00, 127.42, 127.61, 128.12, 128.32, 129.28,
2
2
30.69, 137.52, 140.19; HRMS (EI) anal. calcd for
MeOH] to give desired products 3. Except for known 3a-e,
+
C H N (M ): 232.1000. Found: 232.0998.
16 12 2
1
2-Methyl-6-phenylindolo[1,2-c]quinazoline (3l). Solid;
ꢀ
1
mp 200–201 C (from CH Cl -hexane);
H
NMR
2
2
(
1
2
500 MHz, CDCl ) δ 2.73 (s, 3H), 6.30 (d, J = 8.5 Hz,
3
H), 6.88–6.91 (m, 1H), 7.23–7.26 (m, 1H), 7.41–7.44 (m,
H), 7.50–7.57 (m, 5H), 7.67 (d, J = 8.0 Hz, 1H),
13
Scheme 2. A reaction pathway.
7.73–7.76 (m, 1H), 8.20–8.23 (m, 1H);
C NMR
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BULLETIN OF THE
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KOREAN CHEMICAL SOCIETY
13
(
125 MHz, CDCl ) δ 11.18, 106.99, 114.97, 118.40,
1H), 10.75 (s, 1H); C NMR (125 MHz, CDCl ) δ 22.70,
3
3
1
1
1
3
21.88, 122.53, 123.11, 123.82, 127.19, 127.95, 128.35,
28.38, 129.50, 130.13, 130.44, 130.54, 131.43, 136.46,
100.95, 109.17, 111.72, 115.01, 115.92, 117.21, 119.17,
119.35, 119.58, 119.78, 119.87, 120.35, 122.03, 123.86,
124.94, 125.57, 135.50, 143.22, 165.07; HRMS (EI) anal.
+
40.14, 149.79; HRMS (EI) anal. calcd for C H N (M ):
2
2 16 2
+
08.1313. Found: 308.1311.
calcd for C H N O (M ): 326.1419. Found: 326.1422.
22 18 2
1
1
2-Butylindolo[1,2-c]quinazoline (3m).
Solid; mp
Acknowledgments. This research was supported by Basic
Science Research Program through the National Research
Foundation of Korea (NRF) funded by the Ministry of Edu-
cation (2017R1D1A1B03028226).
ꢀ
18–120 C (from CH Cl -hexane); H NMR (500 MHz,
2 2
1
CDCl ) δ 0.90 (t, J = 7.5 Hz, 3H), 1.39–1.46 (m, 2H),
3
1
7
1
.64–1.70 (m, 2H) 3.10 (t, J = 8.0 Hz, 2H), 7.29–7.37 (m, 2H),
.38–7.42 (m, 2H), 7.67–7.69 (m, 2H), 7.78 (d, J = 8.0 Hz,
H), 8.02–8.04 (m, 1H), 8.80 (s, 1H); C NMR (100 MHz,
13
References
CDCl ) δ 14.28, 23.16, 24.97, 32.12, 109.68, 112.10, 119.10,
3
122.60, 122.95, 123.73, 123.84, 127.21, 127.55, 128.32,
1
. R. Rohini, P. M. Reddy, K. Shanker, A. Hu, V. Radinder,
128.38, 129.41, 130.54, 137.65, 140.32; HRMS (EI) anal.
Eur. J. Med. Chem. 2010, 45, 1200.
+
calcd for C H N (M ): 274.1470. Found: 274.1472.
19
18
2
2. R. Rohini, K. Shanker, P. M. Reddy, V. C. Sekhar,
V. Ravinder, Arch. Pharm. Chem. Life Sci. 2009, 342, 533.
3. K. Kiang, F. G. Mann, A. F. Prior, A. Topham, J. Chem. Soc.
1
2-Butyl-6-Phenylindolo[1,2-c]quinazoline (3n). Solid;
ꢀ
1
mp 138–140 C (from CH Cl -hexane);
H
NMR
2
2
1
956, 1319.
(
(
(
400 MHz, CDCl ) δ 0.94 (t, J = 7.6 Hz, 3H), 1.44–1.53
m, 2H), 1.69–1.77 (m, 2H), 3.20 (t, J = 7.6 Hz, 2H), 6.29
d, J = 8.4 Hz, 1H), 6.87–6.91 (m, 1H), 7.21–7.25 (m, 1H),
3
4
5
. D. Billimoria, M. P. Cava, Heterocycles 1996, 42, 453.
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J. Braz. Chem. Soc. 2010, 21, 897.
7
1
.40–7.44 (m, 2H), 7.48–7.57 (m, 5H), 7.67 (d, J = 8.0 Hz,
H), 7.72–7.76 (m, 1H), 8.12–8.17 (m, 1H); C NMR
6
. G. Battistuzzi, S. Cacchi, G. Fabrizi, F. Marinelli,
L. M. Parisi, Org. Lett. 2002, 4, 1355.
1
3
(
100 MHz, CDCl ) δ 14.33, 23.28, 25.06, 31.92, 112.75,
15.03, 118.47, 121.90, 122.18, 123.11, 123.58, 127.31,
28.11, 128.36, 128.39, 129.50, 129.64, 130.41, 130.58,
7. J. Zhu, H. Xie, Z. Chen, S. Li, Y. Wu, Chem. Commun.
2011, 47, 1512.
3
1
1
1
8
9
. P. Sang, Y. Xie, J. Zou, Y. Zhang, Org. Lett. 2012, 14, 3894.
. H. Zhang, Y. Jin, H. Liu, Y. Jiang, H. Fu, Eur. J. Org. Chem.
2012, 2012, 6798.
31.22, 136.51, 140.17, 149.87; HRMS (EI) anal. calcd for
+
C H N (M ): 350.1783. Found: 350.1781.
2
5 22 2
1
0. Q. Liu, H. Yang, Y. Jiang, Y. Zhao, H. Fu, RSC Adv. 2013,
3, 15636.
1
6
2-Heptylindolo[1,2-c]quinazoline (3o).
Solid; mp
ꢀ
1
8–69 C (from CH Cl -hexane); H NMR (500 MHz,
11. M. Xu, K. Xu, S. Wang, Z.-J. Yao, Tetrahedron Lett. 2013,
54, 4675.
2
2
CDCl ) δ 0.89 (t, J = 6.9 Hz, 3H), 1.27–1.42 (m, 6H),
1
2
3
1
2. (a) S. L. Ho, C. S. Cho, H.-S. Sohn, Synthesis 2015, 47, 216.
b) Y. Jiao, S. L. Ho, C. S. Cho, Synlett 2015, 26, 1081.
.48–1.54 (m, 2H), 1.75–1.82 (m, 2H), 3.21 (t, J = 7.9 Hz,
H), 7.40–7.53 (m, 4H), 7.76–7.81 (m, 2H), 7.91 (d,
(
1
3
(c) S. L. Ho, I. C. Yoon, C. S. Cho, H.-J. Choi, J. Organomet.
Chem. 2015, 791, 13. (d) P. D. Q. Dao, S. L. Ho, H.-J. Lim,
C. S. Cho, J. Org. Chem. 2018, 83, 4140.
J = 8.0 Hz, 1H), 8.12–8.17 (m, 1H), 8.94 (s, 1H); C NMR
125 MHz, CDCl ) δ 14.32, 22.90, 25.30, 29.48, 29.96,
(
3
3
1
1
0.07, 32.05, 109.72, 112.22, 119.16, 122.65, 123.01,
23.79, 123.90, 127.26, 127.61, 128.35, 128.44, 129.45,
1
3. (a) J. M. Yoo, S. L. Ho, C. S. Cho, Synlett 2016, 27, 1383.
(b) B. W. Yang, S. L. Ho, H.-J. Lim, C. S. Cho, J. Organomet.
30.57, 137.73, 140.35; HRMS (EI) anal. calcd for
Chem. 2016, 806, 83. (c) P. D. Q. Dao, H. K. Lee, H.-S. Sohn,
N. S. Yoon, C. S. Cho, ACS Omega 2017, 2, 2953.
+
C H N (M ): 316.1939. Found: 316.1941.
2
2 24 2
(
d) B. W. Yang, P. D. Q. Dao, N. S. Yoon, C. S. Cho,
1
2-Isopropylindolo[1,2-c]quinazoline (3p).
Solid; mp
ꢀ
1
J. Organomet. Chem. 2017, 851, 136. (e) S. L. Ho, P. D. Q. Dao,
C. S. Cho, Synlett 2017, 28, 1811. (f ) P. D. Q. Dao, C. S. Cho,
S. L. Ho, H.-S. Sohn, Curr. Org. Chem. 2018, 22, 85.
114–115 C (from CH Cl -hexane); H NMR (500 MHz,
2
2
CDCl ) δ 1.65 (d, J = 7.5 Hz, 6H), 4.09 (sept, J = 7.0 Hz, 1H),
3
7.38–7.44 (m, 2H), 7.46–7.53 (m, 2H), 7.78–7.80 (m, 1H),
1
4. L. Li, M. Wang, X. Zhang, Y. Jiang, D. Ma, Org. Lett. 2009,
7.90–7.94 (m, 1H), 8.04–8.07 (m, 1H), 8.26–8.30 (m, 1H), 8.94
1
1, 1309.
13
(
1
s, 1H); C NMR (125 MHz, CDCl ) δ 22.65, 27.00, 109.86,
3
15. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire,
Chem. Rev. 2002, 102, 1359.
18.13, 121.67, 122.37, 122.89, 123.34, 124.13, 126.15, 127.39,
1
28.43, 128.47, 128.75, 130.14, 137.62, 140.71; HRMS
16. I. P. Beleskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004,
248, 2337.
+
(EI) anal. calcd for C H N (M ): 260.1313. Found: 260.1311.
18 16 2
1
1
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© 2018 Korean Chemical Society, Seoul & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.bkcs.wiley-vch.de
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