Simple and efficient procedure for the synthesis of novel 1,3-diphenyl-2-azaphenalene derivatives via one-pot multicomponent reactions

Article abstract of DOI:10.1080/00397910903161835

A new, one-pot multicomponent reaction of two molecules of aromatic aldehydes with 2,7-naphthalenediol and ammonium hydrogen phosphate is described as an efficient and direct procedure for the preparation of novel 1,3-diphenyl-2-azaphenalene derivatives i

Full text of DOI:10.1080/00397910903161835

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Simple and Efficient Procedure for
the Synthesis of Novel 1,3-Diphenyl-2-
azaphenalene Derivatives via One-Pot
Multicomponent Reactions
Naser Foroughifar a , Akbar Mobinikhaledi a & Hassan Moghanian a
a Faculty of Sciences, Department of Chemistry, Arak University,
Arak, Iran
Version of record first published: 17 May 2010.
To cite this article: Naser Foroughifar , Akbar Mobinikhaledi & Hassan Moghanian (2010): Simple
and Efficient Procedure for the Synthesis of Novel 1,3-Diphenyl-2-azaphenalene Derivatives via
One-Pot Multicomponent Reactions, Synthetic Communications: An International Journal for Rapid
Communication of Synthetic Organic Chemistry, 40:12, 1812-1821
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Synthetic Communications1, 40: 1812–1821, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903161835
SIMPLE AND EFFICIENT PROCEDURE FOR THE
SYNTHESIS OF NOVEL 1,3-DIPHENYL-2-
AZAPHENALENE DERIVATIVES VIA ONE-POT
MULTICOMPONENT REACTIONS
Naser Foroughifar, Akbar Mobinikhaledi,
and Hassan Moghanian
Faculty of Sciences, Department of Chemistry, Arak University, Arak, Iran
A new, one-pot multicomponent reaction of two molecules of aromatic aldehydes with
2,7-naphthalenediol and ammonium hydrogen phosphate is described as an efficient and
direct procedure for the preparation of novel 1,3-diphenyl-2-azaphenalene derivatives in a
mixture of EtOH-H2O (3:1) under reflux conditions.
Keywords: Condensation; 1,3-diphenyl-2-azaphenalene; multicomponent; naphthalenediol; one-pot reaction
INTRODUCTION
Multicomponet reactions (MCRs) are of increasing importance in organic and
medicinal chemistry.[1–3] MCRs offer significant advantages over conventional
linear-type syntheses for their high degree of atom economy, convergence, ease of
execution, and broad applications. MCRs are particularly useful to generate diverse
chemical libraries of druglike molecules for biological screening.[4,5] There has been
tremendous development in three- or four-component reactions, especially the
Biginelli,[6–8] Passerini,[9,10] Ugi,[11–14] and Mannich[15,16] reactions, which have
further led to a renaissance of MCRs. Nevertheless, great efforts have been and still
are being made to find and develop new MCRs.
Straightforward synthesis of 1-(a-aminobenzyl)-2-naphthol (the Betti base)
from 2-naphthol, benzaldehyde, and ammonia was reported for the first time by
Betti at the beginning of the 20th century.[17] The Betti procedure can be interpreted
as an extension of Mannich condensation, with formaldehyde replaced by an
aromatic aldehyde, the secondary amine replaced by ammonia, and the C-H acid
replaced by an electron-rich aromatic compound such as 2-naphthol.[18] As a conse-
quence of the potential utility of Mannich-type phenolic bases, the amioalkylation of
naphthol derivatives is a subject of current chemical interest.[19–21]
Considering the attention given to the condensation of hydroxyaromatic
compounds with aldehydes and amines or ammonia, it is rather surprising that
Received May 6, 2009.
Address correspondence to Naser Foroughifar, Faculty of Sciences, Department of Chemistry,
Arak University, Arak 38156-879, Iran. E-mail: N_Foroughifar@yahoo.com
1812

SYNTHESIS OF NOVEL 2-AZAPHENALENE DERIVATIVES
1813
products from such reactions involving the use of 2,7-naphthalenediol have not been
described in the literature. This general type of reaction has provided a convenient
route to a variety of complex substances that are accessible only with difficulty by
other methods. It has been found that the course of the condensation and the type
of products obtained depend upon the several factors, including the nature of the
hydroxyaromatic compounds,[22] amine,[23–25] and aldehyde compounds.[26–28]
RESULTS AND DISCUSSION
During the course of our recent studies directed toward the development of
practical, safe, and environmentally friendly procedures for some important
transformations,[29–33] we found a simple and efficient procedure for the synthesis
of novel 1,3-diphenyl-2-azaphenalene derivatives from the condensation of 2,7-
naphthalenediol, aromatic aldehydes, and ammonium hydrogen phosphate in a
mixture of EtOH-H2O (3:1) under reflux conditions (Fig. 1).
For the preliminary study, 2,7-naphthalenediol (1 mmol), benzaldehyde
(2 mmol), and 25% aqueous ammonia (0.5 mL) in ethanol (3 mL) were stirred under
reflux conditions (Betti-type procedure). It was found that 4,9-dihydroxy-1,3-
diphenyl-2, 3-dihydro-2-azaphenalene was obtained with yield of 43% after 30 h. To
improve the yield of the reaction, we carried out this condensation reaction with differ-
ent ammonium salts instead of aqueous ammonia, and the best results were obtained
when 2 equivalents of ammonium hydrogen phosphate were used (Table 1, entry 3).
Figure 1. Synthesis of 1,3-diphenyl-2-azaphenalene derivatives.
Table 1. Optimization of reaction condition for the condensation of 2,7-naphthalenediol, benzaldehyde,
and ammonia
Entry
Ammonium salts
Time (h)
Yield (%)a
1
2
3
4
5
6
7
8
NH3
NH4Cl
30
30
18
30
30
30
30
12
43
0
(NH4)2HPO4
(NH4)2SO4
(NH4)2CO3
(NH4)HSO4
NH4NO3
70
0
58
0
0
85b
(NH4)2HPO4
aIsolated yields.
bThis reaction was carried out in EtOH-H2O (3:1) as a solvent.

1814
N. FOROUGHIFAR, A. MOBINIKHALEDI, AND H. MOGHANIAN
Table 2. Synthesis of 4,9-dihydroxy-1,3-diaryl-2,3-dihydro-2-azaphenalenes
Time
(h)
Yield
(%)b
Mp
(ꢀC)
Entry
Aldehyde (Ar)
Producta
1
12
10
85
83
202–203
230–232
2
3
4
12
9
81
89
223–224
219–220
5
6
10
12
78
75
215–216
203–205
7
8
8
8
90
92
207–209
211–212
9
10
84
208–209
(Continued )

SYNTHESIS OF NOVEL 2-AZAPHENALENE DERIVATIVES
1815
Table 2. Continued
Time
(h)
Yield
(%)b
Mp
(ꢀC)
Entry
10
Aldehyde (Ar)
Producta
12
85
82
199–200
11
12
18
15
196–197
215–217
83
80
13
10
204–206
aThe product were characterized by IR, 1H NMR, 13C NMR, and elemental analysis.
bIsolated yields.
During the course of our investigations of these reaction conditions, we found
that addition of water to the reaction mixture increased the yield of product up to
85% (Table 1, entry 8), probably due to the increase of the solubility of (NH4)2HPO4.
Thus, EtOH-H2O (3:1) was chosen as a solvent for all further reactions.
To extend the preparative utility and generality of this MCR, the reaction of
2,7-naphthalenediol with various aromatic aldehydes, bearing electron-withdrawing
groups (such as nitro, halide), electron-donating groups (such as methyl, methoxy),
and ammonium hydrogen phosphate was carried out in ethanol–water (3:1) under
reflux conditions and afforded the corresponding 1,3-diphenyl-2-azaphenalene
derivatives in good to excellent yields. The results are summarized in Table 2.
On the other hand, aliphatic aldehydes such as propionaldehyde or butyralde-
hyde and heteroaromatic aldehydes such as 2-pyridinecarbaldehyde or furfural were
also examined under the same conditions, but the corresponding products were
isolated in only trace amounts.
The plausible mechanism for this MCR can be explained by the Betti
reaction.[17] 2,7-Naphthalenediol was reacted with aromatic aldehydes and
ammonia in a molar ratio of 1:2:1 to yield naphthoxazine or isomeric Schiff base
similar to 2-naphthol in the Betti reaction. In view of the tautomeric capability of
these condensation products,[27,34,35] the Schiff base intermediate furnished the

1816
N. FOROUGHIFAR, A. MOBINIKHALEDI, AND H. MOGHANIAN
Figure 2. The most probable mechanism for synthesis of 1,3-diphenyl-2-azaphenalene derivatives.
1,3-diphenyl-2-azaphenalene derivatives upon an intermolecular cyclization
(Mannich-type reaction) and keto-enol tautomerization. The most probable
mechanism for this MCR is illustrated in Fig. 2.
CONCLUSION
In conclusion, we have described a novel, efficient, and one-pot procedure for
the preparation of 4,9-dihydroxy-1,3-diaryl-2,3-dihydro-2-azaphenalenes from four-
component condensation reactions of aromatic aldehydes, 2,7-naphthalenediol, and
ammonium hydrogen phosphate in ethanol–water (3:1) under reflux conditions. In
addition to the efficiency and simplicity provided by this procedure, ease of workup,
excellent yields of products, and environmental friendliness make the method advan-
tageous. This work is currently in progress, and the results will be reported in due
course.
EXPERIMENTAL
All products were characterized by a comparison of their spectral [infrared
1
(IR), H NMR, 13C NMR, and elemental analysis] data. All yields refer to isolated
products. IR spectra were prepared on a Galaxy series Fourier transform (FT)–IR
5000 spectrophotometer using KBr discs. NMR spectra were recorded on a Brucker
spectrophotometer (300 MHz) in dimethylsulfoxide (DMSO-d6) using tetramethylsi-
lane (TMS) as an internal standard. Elemental analyses were performed on a Vario
EL III elemental analyzer.
General Procedure for Synthesis of 4,9-Dihydroxy-1,3-diaryl-2,3-
dihydro-2-azaphenalenes
A mixture of 2,7-naphthalenediol (1 mmol), aldehyde (2 mmol), and ammonium
hydrogen phosphate (2 mmol) in ethanol–water (3:1, 4 mL) was stirred under reflux
conditions for an appropriate time as indicated in Table 2. The progress of the reac-
tion was monitored by thin-layer chromatography (TLC). After completion of the
reaction, saturated aqueous NaCl (20 mL) was added to it, the suspension was stirred

SYNTHESIS OF NOVEL 2-AZAPHENALENE DERIVATIVES
1817
for 60 min, and the precipitate was filtered, washed with water, and air dried. The
crude products were washed with a mixture of ethyl acetate=n-hexane, (20 mL, 1:4)
and dried in vacuum at 100 ꢀC for 4 h to afford the pure products.
Characterization Data
4,9-Dihydroxy-1,3-diphenyl-2,3-dihydro-2-azaphenalene (Table 2,
Entry 1). IR (KBr): nmax ¼ 3610, 3377–2850, 1633, 1581, 1516, 1454, 1421, 1323,
1288, 1157, 1041, 977, 827, 754, 702 cmꢁ1 1H NMR (300 MHz, DMSO-d6):
.
d ¼ 9.86 (s, 2H, disappeared on D2O exchange), 7.78 (d, J ¼ 8.1, 2H), 7.35–7.31
(m, 6H), 7.21 (d, J ¼ 7.0, 4H), 6.86 (d, J ¼ 8.0, 2H), 5.44 (s, 2H), 3.12 (br, 1H, disap-
peared on D2O exchange). 13C NMR (75 MHz, DMSO-d6): d ¼ 152.5, 137.1, 130.5,
129.9, 129.4, 128.9, 127.8, 121.9, 115.7, 109.5, 54.2. Anal. calcd. for C24H19NO2: C,
81.56; H, 5.42; N, 3.96. Found: C, 81.42; H, 5.35; N, 3.89.
4,9-Dihydroxy-1,3-di(4-methylphenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 2). IR (KBr): nmax ¼ 3470, 3322–2860, 1626, 1512, 1488, 1365, 1275,
1089, 1014, 1024, 830 cmꢁ1
;
1H NMR (300 MHz, DMSO-d6): d ¼ 9.20 (br, 2H,
disappeared on D2O exchange), 7.63 (d, J ¼ 8.6 Hz, 2H), 7.22 (d, J ¼ 7.3 Hz, 4H),
6.98 (d, J ¼ 7.3 Hz, 4H), 6.85 (d, J ¼ 8.7 Hz, 2H), 5.13 (s, 2H), 3.06 (br, 1H, disap-
peared on D2O exchange), 2.22 (s, 6H); 13C NMR (75 MHz, DMSO-d6):
d ¼ 151.8, 138.0, 131.3, 130.6, 130.1, 128.2, 127.9, 122.9, 115.8, 115.5, 54.1, 20.9.
Anal. calcd. for C26H23NO2: C, 81.86; H, 6.08; N, 3.67. Found: C, 81.71; H, 6.13;
N, 3.52.
4,9-Dihydroxy-1,3-di(4-methoxylphenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 3). IR (KBr): nmax ¼ 3473, 3332–2833, 1626, 1599, 1516, 1489, 1425,
1369, 1261, 1147, 1039, 835, 781, 700 cmꢁ1 1H NMR (300 MHz, DMSO-d6):
;
d ¼ 9.17 (br, 2H, disappeared on D2O exchange), 7.55 (d, J ¼ 7.3 Hz, 2H), 7.10 (d,
J ¼ 6.8, 4H), 6.71–6.63 (m, 6H), 5.12 (s, 2H), 3.68 (s, 6H) 3.10 (br, 1H, disappeared
on D2O exchange); 13C NMR (75 MHz, DMSO-d6): d ¼ 156.6, 150.3, 134.3, 131.7,
129.2, 128.5, 122.8, 115.8, 114.9, 111.2, 55.6, 53.2. Anal. calcd. for C26H23NO4: C,
75.53; H, 5.61; N, 3.39. Found: C, 75.39; H, 5.74; N, 3.28.
4,9-Dihydroxy-1,3-di-(3-methoxyphenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 4). IR (KBr): nmax ¼ 3493, 3300–2833, 1624, 1599, 1516, 1489, 1452,
1
1369, 1147, 1039, 835, 700 cmꢁ1. H NMR (300 MHz, DMSO-d6): d ¼ 9.16 (s, 2H,
disappeared on D2O exchange), 7.57 (d, J ¼ 8.5, 2H), 7.12 (t, J ¼ 7.6, 2H), 6.85 (d,
J ¼ 8.7, 2H), 6.74 (d, J ¼ 7.5, 2H), 6.66–6.63 (m, 4H), 5.14 (s, 2H), 3.65 (s, 6H),
3.02 (br, 1H, disappeared on D2O exchange). 13C NMR (75 MHz, DMSO-d6):
d ¼ 159.4, 150.5, 146.7, 132.1, 129.1, 127.7, 122.7, 120.8, 116.3, 115.2, 114.3, 111.6,
55.3, 53.9. Anal. calcd. for C26H23NO4: C, 75.53; H, 5.61; N, 3.39. Found: C,
75.39; H, 5.54; N, 3.30.
4,9-Dihydroxy-1,3-di-(2-methoyphenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 5). IR (KBr): nmax ¼ 3371, 3234–2837, 1626, 1512, 1417, 1323, 1265,
1163, 1045, 796, 698 cmꢁ1; 1H NMR (300 MHz, DMSO-d6): d ¼ 9.17 (br, 2H, disap-
peared on D2O exchange), 7.61 (d, J ¼ 8.8 Hz, 2H), 6.99 (d, J ¼ 8.1 Hz, 2H),

1818
N. FOROUGHIFAR, A. MOBINIKHALEDI, AND H. MOGHANIAN
6.86–6.68 (m, 4H), 6.60–6.53 (m, 4H), 5.24 (s, 2H), 3.76 (s, 6H), 3.17 (br, 1H, disap-
peared on D2O exchange); 13C NMR (75 MHz, DMSO-d6): d ¼ 157.4, 150.5, 146.7,
132.1, 129.1, 127.7, 122.7, 120.8, 116.3, 115.2, 114.3, 111.6, 55.2, 53.9. Anal. calcd.
for C26H23NO4: C, 75.53; H, 5.61; N, 3.39. Found: C, 75.35; H, 5.72; N, 3.28.
4,9-Dihydroxy-1,3-di-(2-chlorophenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 6). IR (KBr): nmax ¼ 3468–2830, 1624, 1514, 1428, 1396, 1275, 1132,
1
1026, 883, 700, 664 cmꢁ1; H NMR (300 MHz, DMSO-d6): d ¼ 9.28 (br, 2H, disap-
peared on D2O exchange), 7.57 (d, J ¼ 8.6 Hz, 2H), 7.10–7.01 (m, 8H), 6.86 (d,
J ¼ 8.7 Hz, 2H), 5.12 (s, 2H), 3.14 (br, 1H, disappeared on D2O exchange); 13C
NMR (75 MHz, DMSO-d6): d ¼ 150.8, 146.3, 134.1, 132.8, 129.6, 129.4, 128.5,
127.7, 127.3, 122.7, 115.6, 114.5, 53.3. Anal. calcd. for C24H17Cl2 NO2: C, 68.26;
H, 4.06; N, 3.32. Found: C, 68.12; H, 4.21; N, 3.38.
4,9-Dihydroxy-1,3-di-(4-chlorophenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 7). IR (KBr): nmax ¼ 3535, 3387–2862, 1626, 1596, 1512, 1489, 1367,
1275, 1089, 1014, 829 cmꢁ1. 1H NMR (300 MHz, DMSO-d6): d ¼ 9.26 (s, 2H, disap-
peared on D2O exchange), 7.58 (d, J ¼ 8.7, 2H), 7.27 (d, J ¼ 8.2, 4H), 7.09 (d, J ¼ 8.2,
4H), 6.86 (d, J ¼ 8.7, 2H), 5.13 (s, 2H), 3.07 (br, 1H, disappeared on D2O exchange).
13C NMR (75 MHz, DMSO-d6): d ¼ 150.6, 144.1, 132.0, 131.2, 130.2, 128.1, 127.9,
122.8, 115.9, 115.3, 53.3. Anal. calcd. for C24H17Cl2NO2: C, 68.26; H, 4.06; N,
3.32. Found: C, 68.10; H, 4.10; N, 3.25.
4,9-Dihydroxy-1,3-di-(4-bromophenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 8). IR (KBr): nmax ¼ 3487, 3279–2862, 1626, 1599, 1514, 1489, 1367,
1300, 1089, 1014, 829, 781, 756, 687 cmꢁ1; 1H NMR (300 MHz, DMSO-d6): d ¼ 9.29
(br, 2H, disappeared on D2O exchange), 7.63 (d, J ¼ 8.3 Hz, 2H), 7.35 (d, J ¼ 7.9 Hz,
4H), 7.16 (d, J ¼ 7.8 Hz, 4H), 6.92 (d, J ¼ 8.4 Hz, 2H), 5.16 (s, 2H), 3.11 (br, 1H, dis-
appeared on D2O exchange); 13C NMR (75 MHz, DMSO-d6): d ¼ 150.9, 146.0,
131.6, 131.4, 130.1, 128.6, 122.5, 121.6, 115.3, 114.8, 53.4. Anal. calcd. for
C24H17Br2NO2: C, 56.39; H, 3.35; N, 2.74. Found: C, 56.30; H, 3.29; N, 2.80.
4,9-Dihydroxy-1,3-di-(3-bromophenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 9). IR (KBr): nmax ¼ 3484, 3370–2896, 1624, 1594, 1512, 1487, 1311,
1275, 1090, 1132, 881 cmꢁ1
.
1H NMR (300 MHz, DMSO-d6): d ¼ 9.30 (s, 2H,
disappeared on D2O exchange), 7.57 (d, J ¼ 8.7, 2H), 7.35 (d, J ¼ 7.8, 2H),
7.21–7.15 (m, 4H), 7.08 (d, J ¼ 7.6, 2H), 6.85 (d, J ¼ 8.7, 2H), 5.12 (s, 2H), 3.09
(br, 1H, disappeared on D2O exchange). 13C NMR (75 MHz, DMSO-d6):
d ¼ 150.7, 147.7, 131.8, 131.0, 130.4, 129.6, 128.2, 127.5, 122.7, 121.7, 115.5, 115.4,
53.6. Anal. calcd. for C24H17Br2NO2: C, 56.39; H, 3.35; N, 2.74. Found: C, 56.26;
H, 3.37; N, 2.81.
4,9-Dihydroxy-1,3-di-(4-flurophenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 10). IR (KBr): nmax ¼ 3491, 3338–2820, 1625, 1516, 1368, 1276,
1
1119, 1024, 825, 790, 656 cmꢁ1; H NMR (300 MHz, DMSO-d6): d ¼ 9.31 (br, 2H,
disappeared on D2O exchange), 7.60 (d, J ¼ 8.4 Hz, 2H), 7.11 (d, J ¼ 7.6 Hz, 4H),
7.06 (d, J ¼ 7.5 Hz, 4H), 6.87 (d, J ¼ 8.3 Hz, 2H), 5.21 (s, 2H), 3.11 (br, 1H, disap-
peared on D2O exchange); 13C NMR (75 MHz, DMSO-d6): d ¼ 163.0, 150.9,

SYNTHESIS OF NOVEL 2-AZAPHENALENE DERIVATIVES
1819
140.0, 131.7, 130.3, 130.2, 128.2, 122.6, 115.4, 115.1, 53.2. Anal. calcd. for C24H17F2
NO2: C, 74.03; H, 4.40; N, 3.60. Found: C, 73.87; H, 4.53; N, 3.47.
4,9-Dihydroxy-1,3-di-(3-nitrophenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 11). IR (KBr): nmax ¼ 3471, 3276–2864, 1626, 1526, 1512, 1424,
1346, 1321, 1275, 1156, 1024, 832, 699 cmꢁ1 1H NMR (300 MHz, DMSO-d6):
;
d ¼ 9.46 (br, 2H, disappeared on D2O exchange), 8.06 (d, J ¼ 7.5 Hz, 2H), 7.93 (s,
2H), 7.64–7.50 (m, 6H), 6.90 (d, J ¼ 8.8 Hz, 2H), 5.30 (s, 2H), 3.17 (br, 1H, disap-
eared on D2O exchange); 13C NMR (75 MHz, DMSO-d6): d ¼ 151.8, 148.0, 146.3
133.1, 131.6, 129.7, 128.4, 120.8, 123.0, 121.8, 115.2, 114.8, 53.4. Anal. calcd. for
C24H17N3O6: C, 65.01; H, 3.86; N, 9.48. Found: C, 64.82; H, 3.93; N, 9.34.
4,9-Dihydroxy-1,3-di(3,4-dimethoyphenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 12). IR (KBr): nmax ¼ 3493, 3332–2833, 1626, 1599, 1516, 1489,
1
1425, 1369, 1261, 1147, 1039, 835, 781, 700 cmꢁ1; H NMR (300 MHz, DMSO-d6):
d ¼ 9.11 (br, 2H, disappeared on D2O exchange), 7.66 (d, J ¼ 8.7 Hz, 2H), 6.88 (d,
J ¼ 8.5 Hz, 2H), 6.75–6.64 (m, 4H), 6.56 (d, J ¼ 7.6 Hz, 2H), 5.12 (s, 2H), 3.74 (s,
6H), 3.67 (s, 6H), 3.13 (br, 1H, disappeared on D2O exchange); 13C NMR
(75 MHz, DMSO-d6): d ¼ 157.8, 153.6, 150.5, 146.7, 132.1, 129.1, 127.7, 122.7,
120.8, 115.2, 114.3, 111.6, 55.2, 55.0, 53.9. Anal. calcd. for C28H27NO6: C, 71.02;
H, 5.75; N, 2.96. Found: C, 69.84; H, 5.83; N, 2.83.
4,9-Dihydroxy-1,3-di-(4-hydroxyphenyl)-2,3-dihydro-2-azaphenalene
(Table 2, entry 13). IR (KBr): nmax ¼ 3519, 3211–2823, 2696, 1632, 1604, 1543,
1516, 1429, 1309, 1248, 1174, 1130, 831, 773, 657 cmꢁ1 1H NMR (300 MHz,
;
DMSO-d6): d ¼ 9.01 (br, 4H, disappeared on D2O exchange), 7.53 (d, J ¼ 7.4 Hz,
2H), 6.95–6.84 (m, 6H), 6.60–6.50 (m, 4H), 5.08 (s, 2H), 3.03 (br, 1H, disappeared
on D2O exchange); 13C NMR (75 MHz, DMSO-d6): d ¼ 156.4, 150.7, 134.2, 132.0,
129.4, 127.7, 122.6, 116.0, 115.3, 115.0, 53.3. Anal. calcd. for C24H19NO4: C,
74.49; H, 4.97; N, 3.63. Found: C, 74.36; H, 4.86; N, 3.52.
ACKNOWLEDGMENT
We gratefully acknowledge the financial support from the Research Council of
Arak University.
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