Synthesis of spiro[indoline-3,4′-pyrrolo[1,2-a]quinoxalin]-2-one catalyzed by molecular iodine

Article abstract of DOI:10.1016/j.tet.2013.03.102

Molecular iodine catalyzed preparation of spiro[indoline-3,4′- pyrrolo[1,2-a]quinoxalin]-2-one. This reaction between N-(2-aminophenyl)pyrrole and isatins proceeds in CH₃CN at room temperature in good to excellent yields.

Full text of DOI:10.1016/j.tet.2013.03.102

Accepted Manuscript
Synthesis of Spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one Catalyzed by
Molecular Iodine
Abdolali Alizadeh, Javad Mokhtari
PII:
S0040-4020(13)00505-X
10.1016/j.tet.2013.03.102
TET 24193
DOI:
Reference:
To appear in: Tetrahedron
Received Date: 26 November 2012
Revised Date: 7 March 2013
Accepted Date: 26 March 2013
Please cite this article as: Alizadeh A, Mokhtari J, Synthesis of Spiro[indoline-3,4'-pyrrolo[1,2-
a]quinoxalin]-2-one Catalyzed by Molecular Iodine, Tetrahedron (2013), doi: 10.1016/j.tet.2013.03.102.
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ACCEPTED MANUSCRIPT
Leave this area blank for abstract info.
Synthesis of Spiro[indoline-3,4'-pyrrolo
[1,2-a]quinoxalin]-2-one Catalyzed by Molecular Iodine
Abdolali Alizadeh, Javad Mokhtari
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
O
N
R
N
I2 (10 mol %)
CH3CN, r.t
R
NH
O
+
NH2
N
O
N
R'
R'
Molecular iodine catalyzed preparation of spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one. This reaction between N-(2-
aminophenyl)pyrrole and isatins proceeds in CH3CN at room temperature in good to excellent yields.

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2
Synthesis of Spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one Catalyzed by
Molecular Iodine
Abdolali Alizadeh,*Javad Mokhtari
Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran
Abstract— Molecular iodine catalyzed preparation of spiro[indoline-3,4'-pyrrolo[1,2-
a]quinoxalin]-2-one. This reaction between N-(2-aminophenyl)pyrrole and isatins proceeds in
CH3CN at room temperature in good to excellent yields.
1. Introduction
A major challenge of modern drug discovery is the design of efficient chemical reaction
sequences that provide maximum structural complexity and diversity with a minimum number of
synthetic steps to assemble compounds with interesting properties.1 The pyrrolo[1,2-
a]quinoxaline subunit is present in various biologically and medicinally useful molecules, and
many pyrrolo[1,2-a]quinoxaline derivatives are anti-HIV agents A,2a anticancer agents B,2b,2c
additionally, pyrrolo[1,2-a]quinoxalines are also important intermediates for the construction of
5-HT3 receptor agonists C (Figure 1).3
Keywords: Spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one, N-(2-aminophenyl)pyrrole, isatin, molecular iodine
Corresponding author, Tel.: +98 21 8800663; fax: +98 21 88006544; e-mail: aalizadeh@modares.ac.ir

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N
N
N
N
HN
N
O
O
O
S
B
F
Ph
H
HN
N
N
N
A
Br
F3C
N
N
N
C
Figure 1. Biologically active compounds having pyrrolo[1,2-a]quinoxalines unit
The indole ring system is the most ubiquitous heterocycle in nature. Because of the great
structural diversity of biologically active indoles, it is not surprising that the indole ring system
has become an important structural component in many pharmaceutical agents.4 Furthermore,
indoles substituted with heterocyclic rings at the 3-position have been found in a fascinating
array of bioactive natural products and pharmaceutical compounds.5
Considering the above reports, and as part of our program aimed at developing new
methodologies for the preparation of heterocyclic compounds,6 very recently, we have reported
some procedures for the synthesis of spirooxindole fused heterocycles.7 We are currently
investigating the synthesis of various 5'-H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one
via a facile, atom-economical, and one-pot condensation reaction catalyzed by molecular iodine.
2. Results and discussion
Initial studies were focused on the reaction of isatin and N-(2-aminophenyl)pyrrole at room
temperature for 5 h using different solvent in the presence of different catalysts such as

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molecular iodine, ZnCl2, CuCl2, FeCl3, p-TSA and HCl. The results are summarized in Table 1.
As shown in Table 1, our attempt to perform the model reaction by different catalysts succeeded
and the desired product was obtained in good yield in the presence of I2 after reacting in CH3CN
at 25 °C for 5 h (Table 1, entry 5).
Table 1. Synthetic results of 3 under different reactions conditions
O
N
N
NH
O
NH2
N
O
H
N
H
1a
2
3a
Entry
1
Solvent
MeOH
EtOH
Catalyst (mol %)
I2 (20)
Time (h)
Yield (%)a
12
12
5
45
40
82
83
84
<10
20
0
2
I2 (20)
3
CH3CN
CH3CN
CH3CN
CH3CN
CH2Cl2
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
I2 (20)
4
I2 (15)
5
5
I2 (10)
5
6
-
24
12
24
24
24
24
24
7
I2 (20)
8
ZnCl2 (20)
CuCl2 (20)
FeCl3 (20)
p-TSA (20)
HCl (20)
9
0
10
11
12
0
Trace
30
aN-(2-aminophenyl)pyrrol (1 mmol), isatin (1 mmol)
In another attempt, when the reaction was carried out in absence of I2, only a trace amount of the
product was formed after 24 h at 25 °C (Table 1, entry 6). Under the same reaction conditions, a
similar high yield was obtained when the amount of I2 was increased to 15 or 20 mol% (83 and
82% yields, Table 1, entries 3 and 4). With the optimized reaction conditions in hand, we
continued to apply the approach to various isatins. As shown in Table 2. The I2 mediated reaction

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5
of substituted isatins and N-(2-aminophenyl)pyrrole proceeded efficiently to furnish the
corresponding 5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one in moderate to good
yields (Table 2). It is noteworthy that the methodology worked well even for electron
withdrawing and electron releasing substituents in isatin (Table 2, entries 3 and 4).
Table 2. Synthesis of 5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one derivatives
N
O
R
N
I2 (10 mol %)
CH3CN
NH
R
O
NH2
O
N
N
R'
R'
3
1
Product
3a
2
Entry
R
R’
Time (h)
Yield (%)
1
2
3
4
5
6
7
H
H
5
5
5
5
5
5
5
82
79
80
81
84
82
78
Br
NO2
MeO
H
H
3b
H
3c
H
3d
Bn
3e
Br
H
Bn
3f
4-Me-Bn
3g
The molecular structures of all products 3a–g were elucidated from their mass spectrometric
1
analyses, IR, and H NMR and 13C NMR spectra. The mass spectrum of 3a displayed the
molecular ion peak at m/z 287, which is in agreement with the proposed structure. The IR
spectrum of this compound showed absorption bands due to the two NH groups at 3174, 3139
1
and the carbonyl groups at 1707 cm–1. The H NMR spectrum of 3a showed two sharp singlets
for 2NH groups (δ = 4.52 and 8.86 ppm), three multiplets for CH groups of pyrrole ring (5.54,
6.23, and 7.27 ppm) and the aromatic moieties gave rise to multiplets in the aromatic region of
1
the spectrum (δ = 6.59-7.35 ppm). The H-decoupled 13C NMR spectrum of 3a showed 18
distinct resonances in agreement with the suggested structure.

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Although the detailed mechanism of the above reaction remains to be fully clarified, according to
the experimental observation, compound 3a could be formed via condensation of amine group
with isatin, followed by loss of H2O to produce intermediate 4a. Then molecular iodine can
coordinate with the imine nitrogen, promoting nucleophilic attack of the pyrrole, before finally
aromatization of 5a intermediate affords the desired product. Evidence supporting this proposed
mechanism came from the observation that when the intermediate 4a was prepared as a separate
exercise and subsequently reacted with molecular iodine under the same conditions, the expected
product 3a was obtained in a yield similar to that obtained in the one-pot reaction (Scheme 1).
N
N
O
N
NH2
I2
H2O
O
O
N
N
H
H
4a
N
N
I
I
N
H
NH
- I2
Aromatization
3a
O
O
N
N
H
H
5a
Scheme 1. Probing the mechanism for the formation of title compounds
3. Conclusion
In conclusion, we have described a novel molecular iodine mediated procedure for the
preparation of a wide variety of novel spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one by a
reaction of different isatins and N-(2-aminophenyl)pyrrole. The method is simple, convenient,

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7
efficient, and is expected to be a useful synthetic protocol for the synthesis of a wide range of
novel drug-like spiroindolines.
4. Experimental
Melting points were measured on an Electrothermal 9100 apparatus. Elemental analyses for C,
H, and N were performed using a Heraeus CHN-O-Rapid analyzer. IR spectra were recorded on
a Shimadzu IR-460 spectrometer. Mass spectra were recorded on a FINNIGAN-MAT 8430 mass
1
spectrometer operating at an ionization potential of 70 eV. H and 13C NMR spectra were
recorded at 500.1, 299.8 and 125.7, 75.4 MHz, respectively, on a BRUKER DRX 500 and 300-
AVANCE FT-NMR instrument with CDCl3 and DMSO as solvent. The reagents and solvents
used in this work were obtained from Fluka (Buchs, Switzerland) and used without further
purification.
4.1. General synthesis procedure (for example 3a)
To a mixture of isatin 1a (1 mmol) and N-(2-aminophenyl)pyrrol 2a (1 mmol) in 5 mL of
CH3CN was added molecular iodine (0.1 mmol) and mixture of reaction was stirred at 25 °C for
5 h (the progress was monitored by TLC). After completion, the solvent was removed under
reduced pressure and the residue was purified by column chromatography (n-hexane/EtOAc,
4:1).
5'H-Spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one (3a): White crystals; mp: 171-173
ºC; Rf (25% EtOAc/Hexane) 0.25; IR (KBr) (νmax, cm-1): 3174 (NH), 3139 (NH), 1707 (C=O),
1615 (Ar); 1H NMR (CDCl3): δ 4.32 (s, 1H, NH), 5.54 (1H, m, CH of pyrrole), 6.23 (1H, m, CH
3
of pyrrole), 6.47 (1H, d, JHH = 7.7 Hz, CH of Ar), 6.59 (1H, d, 3JHH = 7.7 Hz, CH of Ar), 6.86

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3
(1H, t, JHH = 7.6 Hz, CH of Ar), 6.91 (1H, t, 3JHH = 7.3 Hz, CH of Ar), 7.02 (1H, t, 3JHH = 7.4
Hz, CH of Ar), 7.15 (1H, t, 3JHH = 7.7 Hz, CH of Ar), 7.27 (1H, m, CH of pyrrole), 7.32 (1H, d,
3
13
3JHH = 7.4 Hz, CH of Ar), 7.35 (1H, d, JHH = 7.7 Hz, CH of Ar), 8.86 (1H, s, NH); C-NMR
(CDCl3): δ 60.7 (Cspiro), 105.6 (CH4 of Pyrrole), 109.9 (CH5 of Pyrrole), 110.2 (CH of Ar), 113.6
(CH of Ar), 114.9 (CH of Ar), 115.3 (CH3 of Pyrrole), 118.8 (CH of Ar), 122.5 (CH of Ar),
124.3 (CH of Ar), 124.5 (Cipso), 124.7 (Cipso-N), 125.2 (CH of Ar), 129.6 (CH of Ar), 129.8 (C2
of Pyrrole), 133.7 (Cipso-NH), 140.8 (Cipso-NHCO), 177.8 (C=O); MS (EI, 70 eV): m/z (%) = 287
(M+, 95), 259 (100), 140 (11), 128 (38); Anal. calcd for C18H13N3O (287.32): C, 75.25; H, 4.56;
N, 14.63 %. Found: C, 75.22; H, 4.54; N, 14.60 %.
5-Bromo-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one (3b): White crystals; mp:
110-112 ºC; Rf (25% EtOAc/Hexane) 0.25; IR (KBr) (νmax, cm-1): 3216 (NH), 1720 (C=O), 1610
1
(Ar); H NMR (CDCl3): δ 4.43 (1H, s, NH), 5.54 (1H, m, CH of pyrrole), 6.24 (1H, m, CH of
pyrrole), 6.37 (1H, d, 3JHH = 8.2 Hz, CH of Ar), 6.58 (1H, d, 3JHH = 7.6 Hz, CH of Ar), 6.85 (1H,
3
3
3
t, JHH = 7.6 Hz, CH of Ar), 6.91 (1H, t, JHH = 7.4 Hz, CH of Ar), 7.26 (1H, d, JHH = 6.1 Hz,
CH of Ar), 7.27 (1H, m, CH of pyrrole), 7.31 (1H, d, 3JHH = 7.7 Hz, CH of Ar), 7.42 (1H, s, CH
13
of Ar), 8.96 (1H, s, NH); C-NMR (CDCl3): δ 61.3 (Cspiro), 106.3 (CH4 of Pyrrole), 110.5 (CH5
of Pyrrole), 112.3 (CH of Ar), 114.2 (CH3 of Pyrrole), 115.4 (CH of Ar), 115.6 (C-Br), 115.9
(CH of Ar), 119.4 (CH of Ar), 124.3 (Cipso), 124.7 (Cipso-N), 124.9 (CH of Ar), 128.8 (CH of Ar),
132.3 (C2 of Pyrrole), 133.0 (CH of Ar), 133.8 (Cipso-NH), 140.2 (Cipso-NHCO), 177.8 (C=O);
MS (EI, 70 eV): m/z (%) = 366 (M+, 8), 257 (11), 84 (100), 69 (32); Anal. calcd for
C18H12BrN3O (366.21): C, 59.03; H, 3.30; N, 11.47 %. Found: C, 58.99; H, 3.26; N, 11.44 %.

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5-Nitro-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one (3c): White crystals; mp:
241-243 ºC; Rf (25% EtOAc/Hexane) 0.30; IR (KBr) (νmax, cm-1): 3320 (NH), 3078 (NH), 1727
1
(C=O), 1607 (Ar); H NMR (DMSO-d6): δ 5.50 (1H, m, CH of pyrrole), 6.18 (1H, m, CH of
pyrrole), 6.76 (1H, d, 3JHH = 8.0 Hz, CH of Ar), 6.78 (1H, t, 3JHH = 7.5 Hz, CH of Ar), 6.93 (1H,
t, 3JHH = 7.5 Hz, CH of Ar), 7.08 (1H, s, NH), 7.10 (1H, d, 3JHH = 8.7 Hz, CH of Ar), 7.56 (1H,
3
d, JHH = 8.1 Hz, CH of Ar), 7.60 (1H, m, CH of pyrrole), 7.99 (1H, s, CH of Ar), 8.28 (1H, d,
3JHH = 8.6 Hz, CH of Ar), 11.01 (1H, s, NH); 13C-NMR (DMSO-d6): δ 60.7 (Cspiro), 105.8 (CH of
Ar), 110.7 (CH4 of Pyrrole), 110.7 (CH5 of Pyrrole), 114.8 (CH of Ar), 115.4 (CH3 of Pyrrole),
117.1 (CH of Ar), 118.7 (CH of Ar), 121.1 (CH of Ar), 124.4 (Cipso), 124.6 (Cipso-N), 125.3 (CH
of Ar), 127.6 (CH of Ar), 132.6 (C2 of Pyrrole), 135.2 (Cipso-NH), 143.0 (C-NO2), 149.5 (Cipso
-
NHCO), 177.8 (C=O); MS (EI, 70 eV): m/z (%) = 332 (M+, 12), 303 (100), 288 (26), 258 (82),
83 (65), 57 (85); Anal. calcd for C18H12N4O3 (332.32): C, 65.06; H, 3.64; N, 16.86 %. Found: C,
65.04; H, 3.59; N, 16.81 %.
5-Methoxy-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one (3d): White crystals; mp:
269-271 ºC; Rf (25% EtOAc/Hexane) 0.15; IR (KBr) (νmax, cm-1): 3304 (NH), 1712 (C=O), 1609
(Ar); 1H NMR (DMSO-d6): δ 3.67 (3H, s, OMe), 5.38 (1H, m, CH of pyrrole), 6.14 (1H, m, CH
of pyrrole), 6.70-6.94 (6H, m, 6 CH of Ar), 6.86 (1H, s, NH), 7.49-7.52 (2H, m, 2 CH of Ar),
10.07 (1H, s, NH); 13C-NMR (DMSO-d6): δ 55.9 (OCH3), 61.3 (Cspiro), 105.3 (CH of Ar), 110.5
(CH4 of Pyrrole), 110.8 (CH5 of Pyrrole), 112.1 (CH of Ar), 114.6 (CH of Ar), 115.2 (CH of Ar),
115.4 (CH3 of Pyrrole), 116.4 (CH of Ar), 118.1 (CH of Ar), 124.5 (Cipso), 125.0 (CH of Ar),
126.2 (Cipso-N), 132.6 (C2 of Pyrrole), 136.0 (Cipso-NHCO), 136.1 (Cipso-NH), 155.7 (C-OMe),

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177.6 (C=O); MS (EI, 70 eV): m/z (%) = 317 (M+, 18), 288 (100), 274 (20), 97 (32); Anal. calcd
for C19H15N3O2 (317.35): C, 71.91; H, 4.76; N, 13.24 %. Found: C, 71.87; H, 4.72; N, 13.21 %.
1-Benzyl-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one (3e): White crystals; mp:
104-106 ºC; Rf (25% EtOAc/Hexane) 0.21; IR (KBr) (νmax, cm-1): 3324 (NH), 1718 (C=O), 1608
1
3
(Ar); H NMR (CDCl3): δ 4.32 (1H, s, NH), 4.63 (1H, d, JHH = 15.0 Hz, CH2-N), 4.96 (1H, d,
3JHH = 15 Hz, CH2-N), 5.60 (1H, m, CH of pyrrole), 6.26 (1H, m, CH of pyrrole), 6.77 (2H, d,
3JHH = 6.6 Hz, 2CH of Ar), 6.92 (1H, t, 3JHH = 7.4 Hz, CH of Ar), 7.01 (1H, t, 3JHH = 7.4 Hz, CH
of Ar), 7.08 (1H, t, 3JHH = 7.5 Hz, CH of Ar), 7.25-7.34 (7H, m, 7 CH of Ar), 7.39 (1H, d, 3JHH
=
7.2 Hz, CH of Ar), 7.40 (1H, d, 3JHH = 8.7 Hz, CH of Ar); 13C-NMR (CDCl3): δ 43.6 (CH2), 60.9
(Cspiro), 105.9 (CH4 of Pyrrole), 109.4 (CH5 of Pyrrole), 110.4 (CH of Ar), 111.9 (Cipso), 114.4
(CH of Ar), 115.4 (CH3 of Pyrrole), 116.1 (CH of Ar), 119.8 (CH of Ar), 123.4 (CH of Ar),
124.9 (CH of Ar), 125.8 (CH of Ar), 127.4 (2 CH of Ar), 127.4 (Cipso-N), 127.7 (CH of Ar),
128.8 (2 CH of Ar), 130.2 (CH of Ar), 134.1 (C2 of Pyrrole), 135.6 (Cipso), 138.3 (Cipso-NH),
143.1 (Cipso-NCO), 175.6 (C=O); MS (EI, 70 eV): m/z (%) = 377 (M+, 2), 237 (54), 180 (45),
146 (95), 84 (100); Anal. calcd for C25H19N3O (377.44): C, 79.55; H, 5.07; N, 11.13 %. Found:
C, 79.51; H, 5.03; N, 11.10 %.
1-Benzyl-5-bromo-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one
(3f):
White
crystals; mp: 91-93 ºC; Rf (25% EtOAc/Hexane) 0.27; IR (KBr) (νmax, cm-1): 3326 (NH), 1717
1
3
(C=O), 1604 (Ar); H NMR (CDCl3): δ 4.12 (1H, s, NH), 4.58 (1H, d, JHH = 15.6 Hz, CH2N),
3
4.92 (1H, d, JHH = 15.6 Hz, CH2N), 5.63 (1H, m, CH of pyrrole), 6.28 (1H, m, CH of pyrrole),
6.62 (1H, d, 3JHH = 8.0 Hz, CH of Ar), 6.76 (1H, d, 3JHH = 7.1 Hz, CH of Ar), 6.92 (1H, s, CH of

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3
Ar), 7.00 (1H, t, JHH = 7.2 Hz, CH of Ar), 7.23-7.39 (8H, m, 8CH of Ar), 7.57 (1H, s, CH of
Ar); 13C-NMR (CDCl3): δ 43.6 (CH2), 60.9 (Cspiro), 106.0 (CH4 of Pyrrole), 110.5 (CH5 of
Pyrrole), 110.9 (CH of Ar), 114.4 (CH of Ar), 115.4 (CH3 of Pyrrole), 115.9 (C-Br), 116.2 (CH
of Ar), 120.0 (CH of Ar), 124.7 (Cipso), 125.0 (CH of Ar), 125.0 (Cipso-N), 127.2 (2 CH of Ar),
127.8 (CH of Ar), 128.9 (2 CH of Ar), 129.0 (CH of Ar), 131.7 (C2 of Pyrrole), 133.0 (CH of
Ar), 133.7 (Cipso), 135.1 (Cipso-NH), 142.0 (Cipso-NCO), 175.0 (C=O); MS (EI, 70 eV): m/z (%) =
456 (M+, 4), 429 (14), 114 (66), 85 (96), 70 (92), 57 (100); Anal. calcd for C25H18BrN3O
(456.33): C, 65.80; H, 3.98; N, 9.21 %. Found: C, 65.76; H, 3.94; N, 9.17 %.
1-(4-Methylbenzyl)-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one (3g): White
crystals; mp: 132-134 ºC; Rf (25% EtOAc/Hexane) 0.20; IR (KBr) (νmax, cm-1): 3328 (NH), 1716
(C=O), 1608 (Ar); 1H NMR (CDCl3): δ 2.32 (3H, s, CH3), 4.30 (1H, s, NH), 4.58 (1H, d, 3JHH
15.2 Hz, CH2N), 4.92 (1H, d, 3JHH = 15.2 Hz, CH2N), 5.59 (1H, m, CH of pyrrole), 6.26 (1H, m,
=
3
3
CH of pyrrole), 6.75 (1H, d, JHH = 7.8 Hz, CH of Ar), 6.76 (1H, d, JHH = 7.8 Hz, CH of Ar),
6.90 (1H, t, 3JHH = 7.7 Hz, CH of Ar), 7.00 (1H, t, 3JHH = 7.5 Hz, CH of Ar), 7.08 (1H, t, 3JHH
=
3
3
7.8 Hz, CH of Ar), 7.09 (2H, d, JHH = 7.8 Hz, 2CH of Ar), 7.14 (1H, d, JHH = 7.2 Hz, CH of
Ar), 7.16 (1H, t, 3JHH = 7.7 Hz, CH of Ar), 7.26 (1H, d, 3JHH = 7.8 Hz, CH of Ar), 7.31 (1H, m,
3
3
CH of pyrrole), 7.41 (1H, d, JHH = 8.2 Hz, CH of Ar), 7.49 (1H, d, JHH = 8.6 Hz, CH of Ar);
13C-NMR (CDCl3): δ 21.1 (CH3), 43.4 (CH2), 60.9 (Cspiro), 105.8 (CH4 of Pyrrole), 109.4 (CH5
of Pyrrole), 110.4 (CH of Ar), 114.4 (CH of Ar), 115.4 (CH3 of Pyrrole), 116.1 (CH of Ar),
119.8 (CH of Ar), 123.4 (CH of Ar), 124.9 (CH of Ar), 125.3 (Cipso), 125.6 (Cipso-N), 125.8 (CH
of Ar), 127.4 (2 CH of Ar), 129.5 (2 CH of Ar), 129.7 (Cipso-CH3), 130.2 (CH of Ar), 132.6
(Cipso), 134.2 (C2 of Pyrrole), 137.4 (Cipso-NH), 143.2 (Cipso-NCO), 175.6 (C=O); MS (EI, 70

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12
eV): m/z (%) = 391 (M+, 4), 288 (64), 183 (66), 69 (100), 57 (97); Anal. calcd for C26H21N3O
(391.47): C, 79.77; H, 5.41; N, 10.73 %. Found: C, 79.73; H, 5.37; N, 10.68 %.
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