A direct phosphine-mediated synthesis of polyfunctionalized 1-aminopyrroles from arylglyoxals, phenylhydrazine and acetylene diesters

Article abstract of DOI:10.24820/ark.5550190.p009.912

A new and efficient one-pot synthesis of 1-Aminopyrrole derivatives by three-component reaction of dialkyl acetylenedicarboxylates, phenylhydrazine and arylglyoxals in the presence of triphenylphosphine is described. The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded good yields of products.

Full text of DOI:10.24820/ark.5550190.p009.912

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Organic Chemistry
Arkivoc 2017, part v, 141-147
A direct phosphine-mediated synthesis of polyfunctionalized 1-aminopyrroles
from arylglyoxals, phenylhydrazine and acetylene diesters
Mahboobe Amirani Poorand, Mohammad Anary-Abbasinejad,* Ali Darehkordi
Department of chemistry, Vali-e-Asr University, Rafsanjan, 77176, Iran
Email: m.anary@vru.ac.ir
Received 10-25-2016
Accepted 06-14-2017
Published on line 08-23-2017
Abstract
A new and efficient one-pot synthesis of 1-Aminopyrrole derivatives by three-component reaction of dialkyl
acetylenedicarboxylates, phenylhydrazine and arylglyoxals in the presence of triphenylphosphine is described.
The reactions were performed in dichloromethane at room temperature and neutral conditions and afforded
good yields of products.
NHPh
RO C
CO R
O
2
2
N
PPh - OPPh
OH
3
3
CO R
2
+
CH Cl , rt, 10hr
Ar
2
2
NHNH2
Ar
OH
CO R
2
Ar: 4-ClC H , 4-BrC H , 4-O NC H , C H , 2-Naphthyl, 4-MeC H
12 examples
Yield: 70 - 87%
6
4
6
4
2
6
4
6
5
6
4
R: Me, Et, t-Bu
Keywords: Phenylhydrazine, arylglyoxals, dialkyl acetylenedicarboxylates, 1-Aminopyrrole, triphenylphosphine
DOI: https://doi.org/10.24820/ark.5550190.p009.912
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Poorand, M. A. et al.
Introduction
1,2
Pyrrole moieties are common subunits in numerous natural products and biological and medicinal important
3
3
compounds and some are the building blocks for porphirine synthesis. 1-aminopyrroles are important
4-7
substructures as precursors for the synthesis of biologically active compounds. Despite the wide application
of 1-aminopyrroles, only a few methods are available for their preparation. Direct synthetic routs to these
8
compounds are relative few and the reported methods suffer from severe reaction conditions, formation of
by-products and tedious workup procedures.9
-16
Multicomponent reactions (MCRs), especially three-component reactions, offer significant advantages
over conventional linear-type syntheses because the combination of the reaction components to generate
1
7,18
new products in a single step is easy and economic.
recently attracted many attention for synthesis of a wide range of heterocyclic compounds.
continuation of our previous studies on the application of arrylglyoxals for the synthesis of heterocyclic
Multi-component reactions of arylglyoxals have been
19-21
In
22-25
compounds
here we wish to report a facile route to the synthesis of 1-aminopyrrole derivatives by a
triphenylphosphine mediated three-component reaction between arylglyoxal derivatives, dialkyl
acetylenedicarboxylates (DAADs) and phenylhydrazine (Scheme 1).
Scheme 1. Reaction between triphenylphosphine, arylglyoxals, phenylhydrazine and triphenylphosphine.
Table 1. The scope of the reaction between triphenylphosphine, arylglyoxals, phenylhydrazine and DAADs
4
a
b
c
d
e
f
g
h
i
R
Ar
4-ClC
4-BrC
4-O NC
Yield%*
87
83
82
80
75
70
86
85
Me
Me
Me
Me
t-Bu
t-Bu
Et
6 4
H
6
H
4
2
6
H
4
C
6
H
5
4-BrC
4-ClC
4-BrC
4-ClC
2-Naphthyl
6
H
4
H
6 4
6
H
4
Et
Et
H
6 4
80
j
k
l
t-Bu
Me
Me
4-MeC
4-MeC
2-NaphC
6
H
H
4
79
83
75
6
4
6
H
4
*
Isolated yields. Coditions: CH
2
Cl
2
, room temperature, 10 hs
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Poorand, M. A. et al.
Initially, to investigate the reaction between triphenylphosphine, DAADs, phenylhydrazine and
arylglyoxals, dimethyl acetylenedicarboxylate (DMAD) was added to a mixture of phenylhydrazine and
triphenyphosphine in CH
2
Cl as solvent at room temperature. Then 4-chlorophenylglyoxal monohydrate was
2
added and the progress of the reaction was monitored by TLC. After 10 h, the TLC of the mixture of the
reaction showed only the presence of pyrrole derivative 4a and triphenylphosphine oxide. Silica-gel
chromatography afforded the product 1-Aminopyrrole 4a in 87% yield. To investigate the scope of the
reaction, diferrent DAADs were treated with triphenylphosphine, phenylhydrazine and different arylglyoxals
and the corresponding 1-aminopyrroles 4b-i were obtained in good yields (Table 1).
Results and Discussion
1
The structures of compounds 4a–i were deduced from their elemental analyses and their infrared (IR), H
1
3
1
NMR, and CNMR spectral data. 500-MH
.85, and 6.60 ppm for two methoxy groups protons and the proton of pyrrole ring, respectively. Aromatic
protons resonated between 7.00 and 7.38 ppm. The NH proton resonated at 7.80 ppm as a broad signal. The
Z
H NMR spectrum of 4a exhibited three sharp signals at δ 3.75,
3
13
C NMR spectrum of compound 4a showed 15 distinct resonances in agreement with the proposed structure.
The structural assignments made on the basis of the NMR spectra of compound 4a were supported by its IR
spectrum. The ester carbonyl groups exhibited strong absorption bands at about 1731 and 1713 cm . Finally,
-1
the structure of 4a was unambiguously confirmed by its X-Ray crystal structure (Figure 1).
Figure 1. ORTEP diagram of 4a with atom numbering scheme. Thermal ellipsoids are shown at 50% probability
(CCDC number 1508905).
The suggested mechanism for formation of 1-aminopyrroles by the reaction between triphenylphosphine,
arylglyoxal derivatives, DAADs and phenylhydrazine is showed in Scheme 2. Three component reaction
between triphenylphosphine, DAAD and phenylhydrazine afforded phosphorane 5. The addition of
intermediate 5 to arylgyoxal derivative lead to intermediate 6 which converted to the 1-amininopyrrle
derivative by an intramolecular Wittig reaction and elimination of a molecule of water.
In conclusion, here we report a three-component reaction between dialkyl acetylenedicarboxylates,
phenylhydrazine and arylglyoxals promoted by triphenylphosphine to produce functionalized 1-aminopyrrole
derivatives in good yields. The reaction performed under neutral conditions, and the substances can be mixed
without any activation or modification to afford high yields of products.
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Poorand, M. A. et al.
Ar
RO C
CO R
OH
2
2
NHPh
N
-
-
OPPh3
H O
2
1
Ph3P
NHNHPh
O
Ph3P
PPh3
3
CO R
2
+
NNHPh
RO C
CO R
Ar
2
2
5
NHNH2
CO R
2
RO C
CO R
2
2
4
6
2
Scheme 2. Suggested mechanism for formation of 1-aminopyrrole derivatives 4a-i.
Experimental Section
General. All the utilized arylglyoxals were prepared by the SeO
2
-oxidation of the related aryl methylketones on
the basis of the reported procedure and used as their monohydrates.1 Elemental analyses were performed
26
using a Heraeus CHN-O-Rapidanalyzer. IR spectra were recorded on a Shimadzu IR-470 spectrometer. H, and
13
C NMRspectra were recorded on Bruker DRX-400 Avance spectrometer at 400 and 100 MH , respectively.
Z
The chemicals used in this work purchased from Merck and were used without further purification.
General procedure of dimethyl 5-(4-chlorophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4a). A
mixture of dimethyl acetylenedicarboxylate (142 mg, 1 mmol) in CH
magnetically stirred solution of triphenylphosphine (262 mg, 1 mmol) and phenylhydrazine (108 mg, 1 mmol)
in CH Cl (10 mL). The reaction mixture was then stirred for 1 min. 4-Chlorophenylglyoxal monohydrate (186
2
Cl
2
(3 mL) was added drop wise to a
2
2
mg, 1 mmol) was added, and the reaction mixture was stirred for more 10 hr at room temperature. The
solvent was evaporated, and the residue was purified by column chromatography on silica gel using ethyl
acetate–hexane mixture (4:1 ratio) as eluent to give the product (308 mg, 80%) as a white solid.
Dimethyl 5-(4-chlorophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4a). Yield: (308 mg, 80%); white
1
solid; mp 134-136˚C. IR (KBr) (ῡmax, cm-1): 3333 (NH), 1731, 1713 (C=O). H NMR (CDCl
3
, 400 MHz): δ 3.85(3
3
3
3
H, s), 3.75(3 H, s), 6.60 (2 H, t JHH 8 HZ), 7.00 (1 H, t, JHH 8 H
Z
), 7.19 (1 H, S, Pyr-H), 7.26 (2 H, t, JHH 8 H
Z
), 7.38
13
(
4 H, m), 7.80(1 H, s, NH PhNH). C NMR (CDCl
20.0, 120.1, 122.1, 125.5, 126.3, 126.4, 128.3, 128.4, 130.8, 132.7, 147.2 (aromatic carbons), 165.5, 169.6
C=O). Calcd. for (C20 ): C, 62.42; H, 4.45; N, 7.28%. Found: C, 62.33; H, 4.52; N, 7.35%.
Dimethyl 5-(4-bromophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4b). Yield: (356 mg, 83%); white
3
, 100 MH
Z
): δ 51.6, 52.0 (aliphathic carbon), 113.0, 119.0,
1
(
H17ClN
O
2 4
-
1
1
solid; mp 150-153˚C. IR (KBr) (ῡmax, cm ): 3335 (NH), 1715 (C=O). H NMR (CDCl
3
, 400 MHz): δ 3.75 (3 H, s),
3
3
3
3
.84 (3 H, s), 6.60 (2 H, d, JHH 8 H
Z
), 7.00 (1 H, t JHH 8 H
Z
), 7.19 (1 H, S, Pyr-H), 7.26 (1 H, t, JHH 8 H
Z
), 7.33 (2 H,
3
3
13
d, JHH 8 H
Z
), 7.52(2 H, d, t JHH 8 H
Z
), 7.79 (1 H, s, NH PhNH). C NMR (CDCl
3
, 100 MH ): δ 52.1, 52.5 (aliphathic
Z
carbon), 113.7, 120.7, 121.3, 122.6, 123.1, 125.9, 127.5, 128.8, 129.2, 129.4, 131.1, 147.1 (aromatic carbons),
60.1, 166.1 (C=O). Calcd. for (C20 ): C, 55.96; H, 3.99; N, 6.53%. Found: C, 55.85; H, 4.01; N, 6.60%.
Dimethyl 5-(4-nitrophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4c). Yield: (323 mg, 82%); white
1
H17BrN
O
2 4
-1
solid; mp 165-167˚C. IR (KBr) (ῡmax, cm ): 3321 (NH), 1717 (C=O).
1
3
), 7.01 (1 H, t 3JHH 8 H
H NMR (CDCl
S, Pyr-H), 7.28 (1 H, t, JHH 8 H
NMR (CDCl , 100 MH
3
, 400 MHz): δ 3.77 (3 H, s), 3.87 (3 H, s), 6.61 (2 H, d, JHH 8 H
Z
Z
), 7.25 (1 H,
3
3
3
13
Z
), 7.61 (2 H, d, JHH 8 H
Z
), 7.81 (1 H, s, NH PhNH), 8.26 (2 H, d, t JHH 8 H
Z
). C
3
Z
): δ 52.2, 52.6 (aliphathic carbon), 113.8, 119.6, 120.5, 121.0, 122.8, 124.9, 126.6, 128.1,
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Poorand, M. A. et al.
1
29.5, 139.6, 146.7, 147.4 (aromatic carbons), 159.9, 165.6 (C=O).Calcd. for (C20
17
H N
3
O
6
): C, 60.76; H, 4.33; N,
10.63%. Found: C, 60.83; H, 4.21; N, 10.52%
Dimethyl 4-phenyl-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4d). Yield: (304 mg, 87%); white solid; mp
1
1
6
7
5
1
53-155˚C. IR (KBr) (ῡmax, cm-1): 3263 (NH), 1716 (C=O). H NMR (CDCl
3
, 400 MHz): δ 3.76(3 H, s), 3.85(3 H, s),
3
3
3
3
.61 (2 H, t JHH 8 H
.47(2 H, d, t JHH 8 H
Z
), 6.99 (1 H, t JHH 8 H
Z
), 7.28 (1 H, S, Pyr-H), 7.31 (1 H, t JHH 8 H
), 7.80(1 H, s, NH PhNH). C NMR (CDCl
2.0, 52.5 (aliphathic carbon), 113.7, 119.7, 120.8, 121.7, 122.5, 123.1, 126.1, 127.2, 127.5, 128.9, 129.4,
32.8, 147.9 (aromatic carbons), 160.1, 166.3 (C=O). Calcd. for (C20 ): C, 68.56; H, 5.18; N, 8.00%.Found:
Z
), 7.41 (2 H, t, JHH 8 H
Z
),
3
3
13
Z
), 7.47(2 H, d JHH 8 H
Z
3
, 100 MH ): δ =21.08, 29.7,
Z
18
H N
O
2 4
C, 68.64; H, 5.06; N, 8.19%.
Di-t-butyl 5-(4-bromophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4e). Yield: (309 mg, 75%);
-
1
1
White solid; mp 90-93˚C. IR (KBr) (ῡmax, cm ): 3380 (NH), 1720, 1699 (C=O). H NMR (CDCl
3
, 400 MHz): δ 1.39
), 7.28 (1 H, S, Pyr-H),
). C NMR (CDCl , 100 MH ): δ =
7.4, 81.2, 82.1 (aliphathic carbon), 131.3, 113.3, 120.3, 120.4, 120.6, 121.9, 124.0, 128.8, 129.6, 130.7, 147.9
): C, 60.82; H, 5.69; N, 5.46%. Found: C, 60.71;
3
3
3
(
7
9 H, s), 1.45 (9 H, s), 6.67 (2 H, d, JHH 8 H
Z
), 6.98 (1 H, t JHH 8 H
), 7.70 (1 H, s, NH PhNH, t JHH 8 H
Z
), 7.25 (2H, t, JHH 8 H
Z
3
3
3
13
.32 (2 H, d, JHH 8 H
Z
), 7.51 (2 H, t, JHH 8 H
Z
Z
3
Z
2
(
aromatic carbons), 158.7, 163.3 (C=O). Calcd. for (C26
H29BrN
O
2 4
H, 5.81; N, 5.58%.
Di-t-butyl 5-(4-chlorophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4f). Yield: (257 mg, 70%); White
-
1
1
solid; mp 111-113˚C; mp IR (KBr) (ῡmax, cm ): 3280 (NH), 1720, 1699 (C=O). H NMR (CDCl
3
, 400 MHz): δ 1.39
3
3
3
3
(
9 H, s, ), 1.45 (9 H, s), 6.59 (2 H, d, JHH 8 H
), 7.28 (1 H, s, Pyr-H ), 7.36 (3 H, d, t JHH 8 H
Z
), 6.59 (2 H, d, JHH 8 H
Z
), 6.98 (1 H, t, JHH 8 H
Z
), 7.25 (1 H, d, JHH
8
3
13
H
Z
Z
), 7.70 (1 H, s, NH PhNH). C NMR (CDCl
3
, 100 MHZ): δ 27.4,
81.2, 82.1 (aliphathic carbon), 131.3, 113.3, 120.3, 120.4, 120.6, 121.9, 124.0, 128.8, 129.6, 130.7, 147.9
(
aromatic carbons), 158.7, 163.3 (C=O). Calcd. for (C26 ): C, 60.82; H, 5.69; N, 5.46%. Found: C, 60.94;
H
29ClN
2 4
O
H, 5.53; N, 5.32%.
Diethyl 5-(4-bromophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4g). Yield: (393 mg, 86%); white
-
1
1
3
solid; mp 153-155˚C. IR (KBr) (ῡmax, cm ): 3328 (NH), 1709 (C=O). H NMR (CDCl
3
, 400 MHz): δ 1.21 (3 H, t, JHH
3
), 4.22 (2 H, q, 3JHH 8 H
, arom), 7.18 (1 H, S, Pyr-H) ), 7.27(1 H, t, JHH 8 H
3
), 6.62 (2 H, d, 3JHH 8 H
8
H
Z
), 1.31 (3 H, t, JHH 8 H
Z
Z
), 4.32 (2 H, q, JHH 8 H
Z
Z
, arom), 7.00 (1
3
3
H, t, JHH 8 H
Z
Z
, arom), 7.39(4 H, m, arom), 7.81(1 H, s, NH
13
PhNH). C NMR (CDCl
21.2, 122.6, 125.7, 129.3, 129.4, 131.96, 147.8 (aromatic carbons), 159.7, 165.6 (C=O). Calcd. for
): C, 57.78; H, 4.63; N, 6.13%. Found: C, 57.62; H, 4.77; N, 6.26%.
Diethyl 5-(4-chlorophenyl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4h). Yield: (351 ng, 85%); white
3
, 100 MH
Z
): δ 13.9, 14.0, 61.1, 61.6 (aliphathic carbon), 113.8, 120.2, 120.5, 120.8,
1
(C
22
H21BrN
O
2 4
-1
solid; mp 153-155˚C. IR (KBr) (ῡmax, cm ): 3328 (NH), 1709 (C=O).
1
, 400 MHz): δ 1.23 (3 H, t, 3JHH 8 H
3
), 4.22 (2 H, q 3JHH 8 H
H NMR (CDCl
3
Z
), 1.31 (3 H, t, JHH 8 H
Z
Z
), 4.32 (2 H, q
3JHH 8 H
), 6.62 (2 H, d, 3JHH 8 H
, arom), 7.00 (1 H, t, JHH 8 H
3
, arom), 7.18 (1 H, S, Pyr-H) ), 7.27(1 H, t, JHH 8 H
3
,
Z
Z
Z
Z
13
arom), 7.39(4 H, m, arom), 7.81(1 H, s, NH PhNH). C NMR (CDCl
aliphathic carbon), 114.0, 120.2, 120.5, 120.9, 121.2, 122.6, 126.1, 129.7, 129.9, 131.96, 147.8 (aromatic
carbons), 159.7, 165.6 (C=O). Calcd. for (C22 ): C, 57.78; H, 4.63; N, 6.13%. Found: C, 57.67; H, 4.76; N,
.27%.
Diethyl 4-(naphthalen-2-yl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4i). Yield: (342 mg, 80%); white
3
, 100 MH ): δ 13.9, 14.2, 61.3, 61.8
Z
(
H21ClN
O
2 4
6
-1
1
3
solid; mp 97-99˚C. IR (KBr) (ῡmax, cm ): 3304 (NH), 1720 (C=O). H NMR (CDCl
3
, 400 MHz): δ 1.25 (3 H, t, JHH
8
3
3
3
), 6.67 (2 H, d, 3JHH 8 H
H
Z
3
), 1.31 (3 H, t, JHH 8 H
Z
), 4.24 (2 H, q JHH 8 H
Z
), 4.35 (2 H, q JHH 8 H
Z
Z
, arom), 7.01 (1 H,
3
t, JHH 8 H
Z
, arom), 7.29 (2 H, t, JHH 8 H
Z
, arom) ), 7.48-7.54(2 H, m), 7.60-7.63(1 H, m, arom), 7.85-7.89 (3H, m,
13
naph, py), 7.95(1 H, s, NH PhNH). C NMR (CDCl
3
, 100 MH
Z
): δ 13.9, 14.1, 61.0 (aliphathic carbon), 113.8,
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Poorand, M. A. et al.
119.9, 121.3, 121.5, 125.9, 126.0, 126.1, 126.3, 127.6, 127.9, 128.2, 129.4, 130.4, 132.4, 133.5, 148.0(aromatic
carbons), 165.9(C=O). Calcd. for (C26 ): C, 72.88; H, 5.65; N, 6.54%.Found: C, 73.02; H, 5.51; N, 6.43%
24
H N
2
O
4
Di-t-butyl 1-(phenylamino)-4-(p-tolyl)-1H-pyrrole-2,3-dicarboxylate (4j). Yield: (260 mg, 75%); White solid;
-1
mp 142-144˚C. IR (KBr) (ῡmax, cm ): 3320 (NH), 1725, 1705 (C=O).
1
3
), 6.98 (1 H, t 3JHH
H NMR (CDCl
HZ), 7.02 (1 H, S, Pyr-H), 7.20 (2H, d, 3JHH 8 H
NMR (CDCl , 100 MH
28.8, 129.6, 130.7, 147.9 (aromatic carbons), 159.4, 164.2 (C=O). Calcd. for (C27
.25;%. Found: C, 72.15; H, 7.33; N, 6.38;%.
3
, 400 MHz): δ 1.40 (9 H, s), 1.45 (9 H, s),2.40 (1H, s, CH
3
), 6.61 (2 H, d, JHH 8 H
Z
3
13
8
Z
), 7.26 (2H, m), 7.35 (2 H, d, JHH 8 H
Z
), 7.73 (1 H, s, NH PhNH). C
3
Z
): δ 27.4 (aliphathic carbon), 81.2, 82.1, 131.3, 113.3, 120.3, 120.4, 120.6, 121.9, 124.0,
): C, 72.30; H, 7.19; N,
1
6
H
32
N
2 4
O
Dimethyl 1-(phenylamino)-4-(p-tolyl)-1H-pyrrole-2,3-dicarboxylate (4k). Yield: (316 mg, 83%); white solid; mp
-
1
1
1
(
05˚C. IR (KBr) (ῡmax, cm ): 3310 (NH), 1717 (C=O). H NMR (CDCl , 400 MHz): δ 2.40 (3 H, s), 3.67 (3 H, s), 3.88
3
3
3
3H, s), 6.62 (2 H, d, JHH 8 H
Z
), 7.00 (1 H, t JHH 8 H
Z
), 7.20 (1 H, S, Pyr-H), 7.21-7.24 (2 H, m), 7.26-7.28 (2 H, m ),
3
13
7.35(2 H, d, t JHH 8 H
Z
), 7.81 (1 H, s, NH PhNH). C NMR (CDCl
3
, 100 MH ): δ 21.2, 52.0, 52.5 (aliphathic
Z
carbon), 113.7, 119.5, 120.7, 121.7, 122.5, 126.0, 127.4, 129.4, 129.8, 137.0, 147.9 (aromatic carbons), 160.2,
66.4(C=O). Calcd. for (C21 ): C, 69.22; H, 5.53; N, 7.69%. Found: C, 69.37; H, 5.40; N, 7.56%.
Dimethyl 4-(naphthalen-2-yl)-1-(phenylamino)-1H-pyrrole-2,3-dicarboxylate (4l) Yield: (300 mg, 75%); white
1
20
H N
O
2 4
-
1
1
solid; mp 119˚C. IR (KBr) (ῡmax, cm ): 3286 (NH), 1723 (C=O). H NMR (CDCl
3
, 400 MHz): δ 3.79 (3 H, s), 3.87 (3
), 7.48-7.55 (2 H, m), 7.56-7.61 (1
H, m ), 7.86-7.90 (4 H, m, arom, Pyr-H)), 7.94 (1 H, s, NH PhNH). C NMR (CDCl , 100 MH ): δ 52.1, 52.5
aliphathic carbon), 113.8, 119.8, 121.0, 121.7, 122.6, 125.9, 126.0, 126.3, 126.4, 127.6, 128.0, 128.3, 129.4,
3
3
3
H, s), 3.88, 6.66 (2 H, d, JHH 8 H
Z
), 7.00 (1 H, t JHH 8 H
Z
), 7.29 (3 H, t JHH 8 H
Z
13
3
Z
(
1
30.3, 132.5, 133.5, 147.9 (aromatic carbons), 160.2, 166.4(C=O). Calcd. for (C24
20
H N
2
O ): C, 71.99; H, 5.03; N,
4
7.00%. Found: C, 71.85; H, 5.17; N, 7.13%.
Supplementary Material
1
13
The experimental procedures and IR, H NMR and C NMR spectra associated with this article are available as
supplementary data.
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