Bismuth(III) chloride - Promoted efficient synthesis of perimidine derivatives under ambient conditions

Article abstract of DOI:10.1080/00397910701463011

Various biologically important perimidine derivatives have been efficiently synthesized in excellent yields from naphthalene-1,8-diamine and various ketones in the presence of a catalytic amount of BiCl3. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/00397910701463011

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Bismuth(III) Chloride–Promoted Efficient
Synthesis of Perimidine Derivatives under
Ambient Conditions
a
a b
Junmin Zhang & Songlin Zhang
a
Key Laboratory of Organic Synthesis of Jiangsu Province, College of
Chemistry and Chemical Engineering, Dushu Lake Campus, Suzhou
University, Suzhou, People's Republic of China
b
College of Chemistry and Environmental Science, Hennan Normal
University, Xinxiang, China
Published online: 09 Aug 2007.
To cite this article: Junmin Zhang & Songlin Zhang (2007) Bismuth(III) Chloride–Promoted Efficient Synthesis
of Perimidine Derivatives under Ambient Conditions, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 37:15, 2615-2624, DOI: 10.1080/00397910701463011
To link to this article: http://dx.doi.org/10.1080/00397910701463011
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Synthetic Communications , 37: 2615–2624, 2007
Copyright # Taylor & Francis Group, LLC
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910701463011
Bismuth(III) Chloride–Promoted Efficient
Synthesis of Perimidine Derivatives under
Ambient Conditions
Junmin Zhang
Key Laboratory of Organic Synthesis of Jiangsu Province, College of
Chemistry and Chemical Engineering, Dushu Lake Campus, Suzhou
University, Suzhou, China
Songlin Zhang
Key Laboratory of Organic Synthesis of Jiangsu Province, College of
Chemistry and Chemical Engineering, Dushu Lake Campus, Suzhou
University, Suzhou, China and College of Chemistry and Environmental
Science, Hennan Normal University, Xinxiang, China
Abstract: Various biologically important perimidine derivatives have been efficiently
synthesized in excellent yields from naphthalene-1,8-diamine and various ketones in
3
the presence of a catalytic amount of BiCl .
Keywords: bismuth(III) chloride, catalysis, ketones, naphthalene-1,8-diamine,
perimidines
Perimidines (peri-naphtho-fused pyrimidine systems) are of interest because they
constitute an important class of natural and synthetic products, many of which
exhibit useful biological activity. The interest in pyrido-fused perimidine deriva-
tives stems from the appearance of these heterocyclic systems in many biologi-
[
1,2]
cally active compounds.
the synthesis of perimidine ring structures.
Consequently, there has been ongoing interest in
However, the preparation of
[1–6]
Received January 9, 2006
Address correspondence to Songlin Zhang, Key Laboratory of Organic Synthesis of
Jiangsu Province, College of Chemistry and Chemical Engineering, Dushu Lake
Campus, Suzhou University, Suzhou 215123, People’s Republic of China. E-mail:
zhangsl@suda.edu.cn
2
615

2
616
J. Zhang and S. Zhang
perimidine derivatives using naphthalene-1,8-diamine with ketones has been not
developed a lot. To our knowledge, only protonic acids have been used for this
[
7]
transformation as catalysts. However, their strong acidity led to the occurrence
of side reactions and substrates. Reddy and Rao reported synthesis of 2-methyl-2-
aryl-2,3-dihydro-1H-perimidines using naphthalene-1,8-diamine with aromatic
[7c]
ketones in acetic acid or methanol with moderate product yields (60%). The
methods of acid-catalyzed reactions are not very efficient. Therefore, there is a
need for a new efficient catalyst for this organic transformation.
In recent years, bismuth(III) compounds have received considerable
[8]
attention as mild Lewis acids for an array of organic transformations,
because the catalysts are inexpensive, relatively nontoxic, fairly water insensi-
tive, and environmentally benign reagents. The catalyst bismuth(III) chloride
[
BiCl ] is also commercially available, and we find it can be used for the prep-
3
aration of perimidine derivatives from naphthalene-1,8-diamine and ketones.
However, there are no examples of perimidine derivatives synthesis with
naphthalene-1,8-diamine and ketones using BiCl as a catalyst. Therefore, in
3
this article we report the easy and efficient synthesis of perimidine derivatives
using BiCl as an efficient catalyst under ambient conditions.
3
In the beginning, a systematic study was carried out for the catalytic evalu-
ation of BiCl toward the synthesis of perimidine derivatives. Initially, a blank
3
reaction was conducted using acetophenone and naphthalene-1,8-diamine in
C H OH at room temperature, which resulted in no formation of a new
2
5
product after 48 h (monitored by a thin-layer chromatography, TLC). With the
same substrates, the reaction in C H OH, using catalytic amount of BiCl
2
5
3
(
Thus, in the absence of BiCl , the reaction did not happened at room temperature
10% mol) at room temperature, afforded the product in 82% yield after 6 h.
3
in C H OH. We next investigated the effect of different solvents on the reaction
5
2
yields of products. After screening different solvents, C H OH came out as the
2
5
solvent of choice, which not only afforded the product in the best yield, but also
with the highest reaction rate. The results are summarized in Table 1 (Scheme 1).
Table 1. Comparison of the effect of solvents in the reaction of naphthalene-1,8-dia-
a
mine and acetophenone catalyzed by 10 mol% BiCl
3
b
Yield (%)
Entry
Solvent
Time (h)
1
2
3
4
5
6
7
CH Cl
2
40
6
trace
82
2
C H OH
2
5
CH
THF
3
CN
40
40
40
40
40
15
46
Et O
2
22
PhCH
DMF
3
5
trace
a
All reactions were carried out at room temperature.
Column isolated yields.
b

Perimidine Synthesis
2617
Scheme 1.
.
The method of BiCl -catalyzed synthesis of perimidine derivatives is very
3
simple, efficient, clean, and without any other side products. We also
evaluated the amount of BiCl required for this transformation. As little as
3
5
mol% of BiCl can catalyze the reaction to the same extent using ethanol
3
as solvent, but needs a little longer reaction time (12 h). Further studies
showed that increasing the amount of catalyst did not improve the yield of
the product. To evaluate the efficiency of bismuth(III) salts on the reaction,
we checked the catalytic activities of other BiX salts (for example, BiBr
3
3
and Bi(NO ) ) under the same reaction conditions. We also checked the
3
3
catalytic activity of HCl (a protonic acid) in this system. The results are sum-
marized in Table 2.
In an optimized reaction condition, naphthalene-1,8-diamine (1 mmol)
and ketones (1.2 mmol) in ethanol (5 mL) were mixed with BiCl3
(0.10 mmol) and stirred at room temperature for 3 min–48 h. After the com-
pletion of the reaction (monitored by TLC), a simple workup affords the
products in excellent yield (Scheme 2).
To evaluate the scope and generality of this methodology, a number of
aromatic and aliphatic ketones were further subjected to reaction using a
catalytic amount of BiCl . In general, with aliphatic ketones, the reactions
3
showed better product yields and higher rate than aromatic ketones (Tables
Table 2. Comparison of the effect of catalysts in the reaction of naphthalene-1,
a
8-diamine and acetophenone
Catalyst load
(mol%)
b
Entry
Catalyst
None
Time (h)
Yield (%)
1
2
3
4
5
6
7
48
6
0
81
81
82
83
83
82
HCl
BiCl
BiCl
10
5
3
3
12
6
10
15
10
10
BiCl3
6
.
Bi(NO
3
)
3
5H
2
O
6
BiBr
3
6
a
All reactions were carried out in ethanol at room temperature.
Column isolated yields.
b

2
618
J. Zhang and S. Zhang
Scheme 2.
.
3 and 4). The reactions with aliphatic ketones were carried out at room temp-
erature in C H OH for 30 min.
2
5
Aromatic ketones, such as acetophenone, the conjugating factor of the
phenyl ring, played a key role in affecting the rate of reaction, and the
reaction requires a longer time than aliphatic ketones. In general, with
electron-drawing substituents in the aromatic ketone part, increased yields
of products were obtained, whereas the effect is reversed with electron-
donating substituents. However, the variations in the yields were very little.
p-Nitroacetophenone showed the highest product yields (85%). In benzophe-
none, perhaps because of the conjugation effect of two phenyl rings and the
steric hindrance, the reaction showed the lowest product yields (18%). The
results are summarized in Table 4.
Table 3. Synthesis of different perimidine derivatives using naphthalene-1,8-diamine
and aliphatic ketones
a
b
c
Yield (%)
Entry
1
Ketone
Time
Product
30 min
84
2
3
4
30 min
30 min
30 min
83
92
88
a
All reactions were performed at a 1 mmol scale using 10 mmol% of BiCl
OH at room temperature.
3
in 5 mL
2 5
of C H
b
1
13
All products were well characterized using H, C NMR, and HRMS spectra.
Column isolated yields.
c

Perimidine Synthesis
2619
Table 4. Synthesis of different perimidine derivatives using naphthalene-1,8-diamine
and aromatic ketones
a
b
c
Yield (%)
Entry
1
ketone
Time
6 h
Product
82
83
2
6 h
3
4
7 h
6 h
81
81
5
6
9 h
7 h
80
81
7
8
9
6 h
8 h
85
80
12 h
48 h
79
18
1
0
a
All reactions were performed at a 1 mmol scale using 10 mmol% of BiCl in 5 mL
3
2 5
of C H OH at room temperature.
b
1
13
All products were well characterized using H, C NMR, and HRMS spectra.
Column isolated yields.
c

2
620
J. Zhang and S. Zhang
In summary, we describe a simple, efficient, and ecofriendly method for
the synthesis of perimidine derivatives from various ketones and naphtha-
lene-1,8-diamine using commercially available, inexpensive, relatively
nontoxic bismuth(III) chloride as an efficient catalyst. The ambient con-
ditions (room temperature and without the use of dry solvents or inert atmos-
pheres), high reaction rates, excellent product yields, and easy workup
procedure not only make this methodology an alternative platform to the
conventional acid-catalyzed thermal processes but also makes it significant
under the umbrella of environmentally greener and safer processes because
of using bismuth(III) chloride in ethanol (a greener solvent). Further studies
are currently under way to expand the reaction to other catalysts in our
laboratory.
EXPERIMENTAL
All solvents were used as commercial anhydrous grade without being further
dried. The flash-column chromatography was carried out on Merck silica gel
(
melting-point apparatus. H and C NMR spectra were recorded on a
230–400 mesh). Melting points were recorded on an Electrothermal digital
13
1
Varian Mercury 400-MHz spectrometer as solutions in CDCl . Chemical
3
1
shifts in H NMR spectra are reported in parts per million (ppm, d)
1
3
downfield from the internal standard Me Si (TMS). Chemical shifts in
4
C
NMR spectra are reported relative to the central line of the chloroform
signal (d ¼ 77.50 ppm). High-resolution mass spectra were obtained with a
GCT-TOF instrument.
Typical Experimental Procedure for the Synthesis of Perimidine
Derivatives (3e)
A mixture containing naphthalene-1,8-diamine 1 (1 mmol), ketones
2
(1.2 mmol), and BiCl (10 mmol%) in ethanol (5 mL) was stirred at room
3
temperature for 6 h (monitored by TLC). After completion of the reaction,
solvent was removed under reduced pressure, and the crude product was
subjected to flash column chromatography using silica gel (eluent, 3:1 cyclo-
hexane–EtOAc), which afforded perimidine derivative 3e as a solid. Mp 136–
1
1
388C. H NMR (400 MHz, CDCl ): d 7.59 (d, 2H, J ¼ 7.6 Hz), 7.31–7.13
3
1
3
(
(
m, 7H), 6.57 (d, 2H, J ¼ 7.2 Hz), 4.94 (br s, 2H), 1.85 (s, 3H). C NMR
CDCl , 100 MHz): d 146.21, 140.42, 135.02, 128.93, 128.19, 127.46,
3
þ
126.41, 117.96, 114.00, 106.64, 68.73, 29.75. HRMS(EI ) calcd for
þ
C H N (M ): 260.1313; found: 260.1302.
1
8 16 2

Perimidine Synthesis
2621
Spectral Data for the Perimidine Derivatives 3
1
2
,2-Dimethyl-2,3-dihydro-1H-perimidine(3a): solid, Mp 115–1168C. H
NMR (400 MHz, CDCl ): d 7.24–7.16 (m, 4H), 6.52 (d, 2H, J ¼ 7.2 Hz),
3
1
.21 (br s, 2H), 1.52 (s, 6H); C NMR (CDCl , 100 MHz): d 140.72,
3
4
3
þ
135.04, 127.47, 117.52, 113.36, 106.35, 65.00, 29.28. HRMS(EI ) calcd.
þ
for C H N (M ): 198.1157; found: 198.1149.
1
3 14 2
1
2
,2-Diethyl-2,3-dihydro-1H-perimidine(3b): solid, Mp 94–958C. H NMR
(
400 MHz, CDCl ): d 7.25–7.14 (m, 4H), 6.54 (d, 2H, J ¼ 6.8 Hz), 4.77
3
1
3
(
br s, 2H), 1.77 (q, 4H, J ¼ 7.4 Hz), 0.97 (t, 6H, J ¼ 7.4Hz); C NMR
(
CDCl , 100 MHz): d 138.24, 132.66, 125.09, 114.59, 110.80, 103.54,
3
þ
þ
6
6.88, 28.47, 6.02. HRMS(EI ) calcd. for C H N (M ): 226.1470; found:
1
5 18 2
2
26.1459.
0
0
0
1
1
H,3 H-spiro[cyclopentane-1,2 -perimidine](3c): solid, Mp 85–868C. H
NMR (400 MHz, CDCl ): d 7.23-7.15 (m, 4H), 6.50 (d, 2H, J ¼ 7.2 Hz),
3
1
.36 (br s, 2H), 1.89 (s, 4H), 1.82 (s, 4H). C NMR (CDCl , 100 MHz): d
3
4
1
3
41.46, 135.15, 127.34, 117.77, 114.18, 106.72, 76.52, 39.79, 23.48.
þ
þ
HRMS(EI ) calcd. for C H N (M ): 224.1313; found: 224.1304.
5 16 2
1
0
0
0
1
1
H,3 H-spiro[cyclohexane-1,2 -perimidine](3d): solid, Mp 110–1118C. H
NMR (400 MHz, CDCl ): d 7.25–7.12 (m, 4H), 6.49 (d, 2H, J ¼ 6.8 Hz), 4.43
3
1
br s, 2H), 1.75 (s, 4H), 1.61 (s, 4H), 1.52 (s, 2H). C NMR (CDCl ,
3
(
3
1
2
2
00 MHz): d 140.38, 135.07, 127.48, 117.42, 113.73, 106.36, 65.79, 37.29,
þ
þ
5.68, 22.76. HRMS(EI ) calcd. for C H N (M ): 238.1470; found:
1
6 18 2
38.1462.
2
-Methyl-2-phenyl-2,3-dihydro-1H-perimidine(3e): solid, Mp 136–1388C.
1
H NMR (400 MHz, CDCl ): d 7.59 (d, 2H, J ¼ 7.6 Hz), 7.31–7.13 (m, 7H),
3
1
3
6
1
1
.57 (d, 2H, J ¼ 7.2 Hz), 4.94 (br s, 2H), 1.85 (s, 3H). C NMR (CDCl ,
3
00 MHz): d 146.21, 140.42, 135.02, 128.93, 128.19, 127.46, 126.41,
17.96, 114.00, 106.64, 68.73, 29.75. HRMS(EI ) calcd. for
þ
þ
C H N (M ): 260.1313; found: 260.1302.
18 16 2
2
1
7
-Methyl-2-(4-chlorophenyl)-2,3-dihydro-1H-perimidine(3f): solid, Mp
1
29–1308C. H NMR (400 MHz, CDCl ): d 7.51 (d, 2H, J ¼ 7.6 Hz),
3
.25–7.14 (m, 6H), 6.58 (d, 2H, J ¼ 7.2 Hz), 4.85 (br s, 2H), 1.82 (s, 3H).
1
3
C NMR (CDCl , 100 MHz): d 145.08, 140.22, 135.01, 133.84, 129.02,
3
þ
128.01, 127.48, 118.20, 114.21, 106.83, 68.35, 30.01. HRMS(EI ) calcd.
þ
for C H N Cl(35) (M ): 294.0924; found: 294.0887. HRMS(EI ) calcd.
þ
1
8 15 2
þ
for C H N Cl(37) (M ): 296.0894; found: 296.0886.
18 15 2
2
1
-Methyl-2-(2-chlorophenyl)-2,3-dihydro-1H-perimidine(3g): solid, Mp
1
57–1588C. H NMR (400 MHz, CDCl ): d 7.54 (d, 2H, J ¼ 7.2 Hz),
3

2
622
J. Zhang and S. Zhang
1
3
7
.28–7.00 (m, 8H), 6.58 (d, 2H, J ¼ 7.2 Hz), 5.62 (br s, 2H), 1.96 (s, 3H).
C
NMR (CDCl , 100 MHz): d 142.65, 140.09, 134.96, 132.29, 131.86, 129.23,
3
þ
þ
127.50, 127.38, 117.99, 114.02, 107.34, 106.22, 69.53, 28.90. HRMS(EI )
þ
calcd. for C H N Cl(35) (M ): 294.0924; found: 294.0897. HRMS(EI )
1
8 15 2
þ
calcd. for C H N Cl(37) (M ): 296.0894; found: 296.0865.
18 15 2
2
-Methyl-2-(4-bromophenyl)-2,3-dihydro-1H-perimidine(3h): solid, Mp
1
126–1288C. H NMR (400 MHz, CDCl ): d 7.44–7.13 (m, 8H), 6.55
3
1
3
(
d, 2H, J ¼ 7.2 Hz), 4.76 (br s, 2H), 1.80 (s, 3H). C NMR (CDCl3,
1
1
00MHz): d 145.63, 140.15, 135.01, 131.98, 128.35, 127.47, 122.04,
18.27, 114.27, 106.92, 68.44, 30.05. HRMS(EI ) calcd. for
þ
þ
C H N Br(81) (M ): 340.0398; found: 340.0370.
18 15 2
2
1
-Methyl-2-(2-bromophenyl)-2,3-dihydro-1H-perimidine(3i): solid, Mp
1
65–1668C. H NMR (400 MHz, CDCl ): d 7.59 (d, 1H, J ¼ 8 Hz), 7.48
3
(d, 1H, J ¼ 7.6 Hz),7.23–6.94 (m, 6H), 6.59 (d, 2H, J ¼ 6.8 Hz), 5.73 (br
s, 2H), 1.96 (s, 3H). C NMR (CDCl , 100 MHz): d 144.00, 140.06,
3
1
3
1
1
3
35.84, 134.98, 129.49, 129.45, 127.92, 127.49, 121.13, 117.92, 114.16,
þ
þ
06.11, 69.88, 28.86. HRMS(EI ) calcd. for C H N Br(81) (M ):
1
8 15 2
40.0398; found: 340.0362.
2
-Methyl-2-(4-fluorophenyl)-2,3-dihydro-1H-perimidine(3j): solid, Mp
1
156–1588C. H NMR (400 MHz, CDCl ): d 7.61-7.57 (m, 2H), 7.24–7.17
3
(
m, 4H), 6.95 (t, 2H, J ¼ 8.4 Hz), 6.63 (d, 2H, J ¼ 6.8 Hz), 5.13 (br s, 2H),
1
3
1
1
1
(
.87 (s, 3H). C NMR (CDCl , 100 MHz): d 162.54 ( J ¼ 244.7 Hz),
3
CF
3
42.16, 140.44, 135.03, 128.36 ( J ¼ 8.2 Hz), 127.49, 118.00, 115.64
CF
2
þ
JCF ¼ 21.4 Hz), 114.03, 106.61, 68.22, 29.65. HRMS(EI ) calcd. for
þ
C H N F (M ): 278.1219; found: 278.1210.
18 15 2
2
-Methyl-2-(4-nitrophenyl)-2,3-dihydro-1H-perimidine(3k): solid, Mp
1
192–1938C. H NMR (400 MHz, CDCl ): d 8.02 (d, 2H, J ¼ 8.8 Hz), 7.64
3
(
s, 2H), 1.79 (s, 3H). C NMR (CDCl , 100 MHz): d 154.65, 147.50,
d, 2H, J ¼ 8.8 Hz), 7.25–7.14 (m, 4H), 6.59 (d, 2H, J ¼ 7.2 Hz), 4.86 (br
3
1
3
1
3
39.73, 135.00, 127.57, 124.20, 118.74, 114.74, 107.50, 107.29, 68.46,
þ
þ
0.35. HRMS(EI ) calcd. for C H N O (M ): 305.1164; found: 305.1156.
18 15 3 2
2
-Methyl-2-p-tolyl-2,3-dihydro-1H-perimidine(3l): solid, Mp 117–1198C.
1
H NMR (400 MHz, CDCl ): d 7.47 (d, 2H, J ¼ 7.6 Hz), 7.24–7.08
3
(
1
m, 6H), 6.55 (d, 2H, J ¼ 6.8 Hz), 4.85 (br s, 2H), 2.27 (s, 3H),1.83 (s, 3H).
3
C NMR (CDCl , 100 MHz): d 143.42, 140.73, 137.86, 135.05, 129.59,
3
þ
127.45, 126.32, 117.73, 113.91, 106.37, 68.45, 29.71, 21.42. HRMS(EI )
calcd. for C H N (M ): 274.1470; found: 274.1461.
þ
1
9 18 2
2
-Methyl-2-(4-methoxyphenyl)-2,3-dihydro-1H-perimidine(3m): solid, Mp
1
178–1808C. H NMR (400 MHz, CDCl ): d 7.56 (d, 2H, J ¼ 8.4 Hz),
3

Perimidine Synthesis
2623
7
s, 2H), 3.75 (s, 3H),1.88 (s, 3H). C NMR (CDCl , 100 MHz): d 159.43,
.24–7.17 (m, 4H), 6.81 (d, 2H,J ¼ 8.4 Hz), 6.63 (d, 2H, J ¼ 6.4 Hz), 5.21 (br
1
3
3
1
40.65, 138.16, 135.02, 127.82, 127.48, 117.77, 114.10, 113.81, 106.44,
þ þ
8.33, 55.70, 29.19. HRMS(EI ) calcd. for C H N O (M ): 290.1419;
19 18 2
6
found: 290.1411.
2
,2-Diphenyl-2,3-dihydro-1H-perimidine(3n): solid, Mp 209–2108C.
1
H NMR (400 MHz, CDCl ): d 7.47–7.11 (m, 14H), 6.59 (s, 2H), 5.18 (br
1
s, 2H). C NMR (CDCl , 100 MHz): d 145.34, 140.69, 135.03, 128.78,
128.50, 128.25, 127.47, 117.99, 114.26, 106.45, 73.67. HRMS(EI ) calcd.
þ
for C H N (M ): 322.1470; found: 322.1461.
3
3
3
þ
2
3 18 2
ACKNOWLEDGMENT
We thank the Key Laboratory of Organic Synthesis of Jiangsu Province,
Suzhou University and the Innovator Foundation of Colleges and Universities
of Henan Province for financial support.
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1
. Undheim, K.; Benneche, T. Comprehensive Heterocyclic Chemistry;
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3
. Pozharskii, A. F.; Dalnikovskaya, V. V. Russ. Chem. Rev. (Eng. Transl.) 1981, 50,
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. (a) Vanden Eynde, J.-J.; Fromont, D. Bull. Chim. Belg. 1997, 106, 393;
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