Synthesis and nucleophilic reactions of N-(1-Naphthyl)-3,4-methylenedioxybenzyl-idinehomophthalisoimidium perchlorate

Article abstract of DOI:10.1081/SCC-120002123

N-(1-Naphthyl)-3,4-methylenedioxybenzylidinehomophthalisoimidium perchlorate 6 was obtained via treatment of N-(1-naphthyl)-3,4-methylenedioxybenzylidine homophthalamic acid 5 with perchloric acid in acetic anhydride. The behaviour of 6 towards active methylene-containing compounds, Grignard reagents and aromatic primary amines and hydrocarbons, has been investigated.

Full text of DOI:10.1081/SCC-120002123

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SYNTHESIS AND NUCLEOPHILIC REACTIONS OF N-
(1-NAPHTHYL)- 3,4-METHYLENEDIOXYBENZYL-
IDINEHOMOPHTHALISOIMIDIUM PERCHLORATE
M. E. Azab a , H. M. F. Madkour a & M. R. Mahmoud a
a Synthetic Org. Chem. Lab. , Chem. Dept. , Faculty of Science , Ain Shams University ,
Abbassiya, Cairo, Egypt
Published online: 16 Aug 2006.
To cite this article: M. E. Azab , H. M. F. Madkour & M. R. Mahmoud (2002) SYNTHESIS AND NUCLEOPHILIC REACTIONS OF
N-(1-NAPHTHYL)- 3,4-METHYLENEDIOXYBENZYL-IDINEHOMOPHTHALISOIMIDIUM PERCHLORATE, Synthetic Communications:
An International Journal for Rapid Communication of Synthetic Organic Chemistry, 32:3, 393-402
To link to this article: http://dx.doi.org/10.1081/SCC-120002123
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SYNTHETIC COMMUNICATIONS, 32(3), 393–402 (2002)
SYNTHESIS AND NUCLEOPHILIC
REACTIONS OF N-(1-NAPHTHYL)-
3,4-METHYLENEDIOXYBENZYL-
IDINEHOMOPHTHALISOIMIDIUM
PERCHLORATE
M. E. Azab, H. M. F. Madkour,* and
M. R. Mahmoud
Synthetic Org. Chem. Lab., Chem. Dept.,
Faculty of Science, Ain Shams University,
Abbassiya, Cairo, Egypt
ABSTRACT
N-(1-Naphthyl)-3,4-methylenedioxybenzylidinehomophthali-
soimidium perchlorate 6 was obtained via treatment of N-(1-
naphthyl)-3,4-methylenedioxybenzylidine homophthalamic
acid 5 with perchloric acid in acetic anhydride. The behaviour
of
6 towards active methylene-containing compounds,
Grignard reagents and aromatic primary amines and hydro-
carbons, has been investigated.
*Corresponding author.
393
Copyright & 2002 by Marcel Dekker, Inc.
www.dekker.com

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394
AZAB, MADKOUR, AND MAHMOUD
A connection with our previous interest in developing new approach
for the synthesis of heterocycles utilizing readily obtainable starting
materials,1–4 we report in the present work the synthesis of some new
heterocylic systems utilizing the title compound.
Thus, when 3,4-methylenedioxybenzaldehyde was condensed with
dimethyl homophthalate in the presence of sodium hydride as a condensing
agent, the Z-half-ester 1 was obtained in approximately 90% yield (cf.
Scheme 1). The preferential formation of the Z-configuration for the half-
ester may be rationalized by considering the high strain associated with the
E-isomer due to steric interference between the ortho-carboxyphenyl and
the bulky substituted aryl group.
Scheme 1.
The half-ester 1 was saponified to the corresponding acid 2. The struc-
ture assigned for the dicarboxylic acid 2 was based on its spectroscopic data.
A chemical evidence for the structure assigned for the acid 2 was obtained
from its conversion to the corresponding anhydride 3 by the action of acetyl
chloride (cf. Scheme 2).
Compound 3 was subjected to an internal Friedel-Crafts acylation
reaction with anhydrous aluminium chloride in dry acetylene tetrachloride
to afford the respective oxoacid 4 in good yield (78%).
The assignment of the indenone structure 4 was based on analytical
and spectroscopic data as well as its yellow color which is characteristic for
indenones, its solubility in sodium carbonate solution and the formation of
its DNP on reacting with dinitrophenyl hydrazine.
3,4-Methylenedioxybenzylidine homophthalic anhydride
3
was
allowed to react with 1-naphthylamine in benzene to give 2-[N-(1-naphthyl)-
carboxamido]-3,4-methylene-dioxybenzylidinephenylacetic acid (5). The
interaction of 1-naphthylamine with compound 3 takes place on the benzoyl

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SYNTHESIS OF NEW HETEROCYCLIC SYSTEMS
395
Scheme 2.
carbonyl function rather than the cinnamoyl carbonyl function. This is due
to two reasons; first, the benzoyl carbonyl function is sterically favorable,
second, the electrophilicity of the benzoyl carbonyl function is more than
that of the cinnamoyl moiety.
The homophthalamic acid derivative
5 was transformed to
N-(1-naphthyl)-3,4-methylenedioxybenzylidine homophthalisoimidium per-
chlorate 6 by the action of perchloric acid in acetic anhydride.5
It was of interest to study the reaction of the salt 6 with active-
methylene compounds in the presence of pyridine. When 6 was allowed to
react with ethyl acetoacetate, diethyl malonate and/or ethyl cyanoacetate,
good yields of the isoquinolinones 7a–c were obtained.
Reaction of 6 with benzyl magnesium chloride, phenyl-and cyclohexyl
magnesium bromides yielded the aralkyl-2-[N-(1-naphthyl)carboxamido]-
3,4-methylenedioxy-benzylidinebenzyl ketone 8a–c.
Reaction of compound 6 with aromatic hydrocarbons namely;
toluene, anisole and/or cumene in the presence of anhydrous aluminium
chloride, afforded good yields of the hydroxy-3,4-methylenedioxybenzyli-
dine homophthalimidine derivatives 9a–c.
When nitrogen nucleophiles such as primary aromatic amines namely;
aniline, p-toluidine, p-anisidine, p-chloroaniline and/or benzyl amine
react with the salt 6, N,N0-disubstituted-3,4-methylenedioxybenzylidine
homophthalamides 10a–c were isolated. No evidence for the formation of

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396
AZAB, MADKOUR, AND MAHMOUD
acidic products reÈsulting from the attack at the alternative site of the iso-
imidium salt (C¼N H).
EXPERIMENTAL
All melting points are not corrected, the IR spectra were measured on
a Unicam SP 1200 spectrophotometer using KBr Wafer technique. The
mass spectra were determined with A.E.I.M.S. 12 single focusing mass spec-
trometer and the percentage of the relative abundance of a peak is shown in
brackets and follows the m/z value. The 1H-NMR spectra were measured on
a Varian EM 360 instrument operating at 60 MHz in DMSO-d6 or CDCl3
solution. Compounds 1–5 were prepared according to the methods
described in literature.6–9 The physical characteristics of the new compounds
are listed in Table 1.
Reaction of 3,4-Methylenedioxybenzaldehyde with
Dimethyl Homophthalate; Formation of Methyl-b-(3,4-
methylenedioxyphenyl)-a-(2-carboxyphenyl)acrylate 1
A mixture of the aldehyde (15.01 g; 0.10 mol), dimethyl homophthalate
(32.2 g; 0.15 mol), and sodium hydride (3.6 g, 0.15 mol) in 150 mL of dry
benzene was stirred for 60 min at 60–70ꢀC. The solid deposited was filtered
off, dissolved in NaHCO3 solution (10%) then acidified with dil HCl-ice.
The half ester 1 separated as a colourless crystalline solid which was
recrystallized from benzene (cf. Table 1).
IR spectrum of 1 exhibited strong bands at 1675 and 1720 cmÀ1 for
aryl acid and a,b-unsaturated ester groups respectively. On the other hand,
the 1H-NMR (DMSO-d6) of the half-ester 1 exhibited the following signals:
d 3.28 (s, 3H, COOMe), 6.42 (s, 2H, O-CH2-O), 7.49 (s, 1H, CH¼C),
7.77–8.25 (m, 4H, Ar-H), 8.40–8.71 (m, 3H, Ar-H of piperonyl moiety)
and 10.84 (s, 1H, COOH).
Saponification of the Half-Ester 1; Formation of 3,4-
Methylenedioxybenzylidine Homophthalic Acid 2
The crystalline half-ester 1 (3.3 g; 0.01 mol) was heated under reflux in
35 mL of aqueous sodium hydroxide solution (10%) for 4 h. The alkaline
solution was cooled, acidified with cold dilute hydrochloric acid and the

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SYNTHESIS OF NEW HETEROCYCLIC SYSTEMS
397
Table 1. Physical Characteristics for New Compounds
Analysis
(Found/Cald.)
Solvent of
Crystallization
M.P. (ꢀC)
Mol.
Formula
(M. wt.)
Compd.
No.
Yield
(%)
C%
H%
N%
Cl%
1
152–154
(B)*
88
90
65
78
46
42
41
36
38
69
65
72
32
35
42
73
69
60
54
70
C18H14O6
(326)
66.61
66.26
65.01
65.38
69.92
69.39
69.49
69.39
74.35
74.14
62.05
62.40
74.42
74.58
74.38
74.71
72.87
72.73
79.82
79.84
79.63
79.68
78.51
78.73
79.55
79.84
77.17
77.42
80.03
80.15
77.13
77.34
77.33
77.57
75.17
75.28
72.08
72.46
77.19
77.57
4.17
4.29
4.14
3.85
3.56
3.40
3.21
3.40
4.19
4.35
3.61
3.28
4.79
4.71
4.66
4.29
4.59
4.81
4.81
4.89
4.66
4.63
5.88
5.77
5.14
4.89
4.91
4.74
5.29
5.38
4.79
4.69
5.21
4.94
4.90
4.80
4.13
4.21
5.20
4.94
–
–
–
–
2
212–214
(B/M)
138–139
(L.P./B)
205–207
(B/M)
190–200
(M)
C17H12O6
(312)
–
–
–
–
3
C
17H10O5
(294)
–
–
–
–
4
C
17H10O5
(294)
–
–
–
–
5
C27H19NO5
(437)
3.70
3.20
4.42
2.70
2.77
2.64
5.59
5.45
2.58
2.50
2.61
2.74
2.61
2.82
2.87
2.78
2.78
2.74
2.82
2.66
2.82
2.60
5.10
5.47
5.50
5.32
5.11
5.17
5.28
5.12
5.23
5.32
–
–
6
196
(T)
C27H17NO8Cl
(518.5)
6.86
6.85
–
7a
7b
7c
8a
8b
8c
9a
9b
9c
10a
10b
10c
10d
10e
92–94
(L.P.)
210–212
(B)
C
33H25NO6
(531)
–
C
32H22N2O5
(514)
–
–
110–112
(L.P.)
220–221
(T)
C34H27NO7
(561)
–
–
C
34H25NO4
(511)
–
–
240–242
(M)
C33H23NO4
(497)
–
–
213–215
(B)
260
C
33H29NO4
(503)
–
–
C34H25NO4
(511)
–
(B/M)
206
(M)
–
C
34H25NO5
(527)
–
–
182–184
(B)
C36H29NO4
(539)
–
–
214–216
(B)
C33H24N2O4
(512)
–
–
220–222
(T)
C
34H26N2O4
(526)
–
–
191–192
(B)
C
34H26N2O5
(542)
–
–
146–148
(T)
253
C33H23N2O4Cl
(546.5)
6.30
6.50
–
C34H26N2O4
(526)
(M)
–
*B ¼ benzene; M ¼ methanol; L.P. ¼ light petroleum 80–100ꢀC; T ¼ toluene.

ORDER
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AZAB, MADKOUR, AND MAHMOUD
precipitated substance was filtered off and recrystallized from the suitable
solvent to give 2 (cf. Table 1).
IR spectrum of 2 showed a single absorption band at 1680 cmÀ1
for both aryl conjugated and a,b-unsaturated acids. The 1H-NMR
(CDCl3) of 2 indicates the presence of olefinic and aromatic protons: d
6.49 (s, 2H, O-CH2-O), 7.46 (s, 1H, CH¼C), 7.70–8.34 (m, 4H, Ar-H),
8.52–8.77 (m, 3H, Ar-H of piperonyl moiety), 10.74 (s, 1H, CO2H) and
10.84 (s, 1H, CO2H). The MS of 2 exhibited the following peaks: 312
(50), 294 (53), 249 (20), 193 (33), 165 (100), 152 (62), 135 (45), 63 (82)
and 51 (39).
Conversion of the Diacid 2 to 3,4-Methylenedioxybenzylidine
Homophthalic Anhydride 3
Refluxing the diacid 2 (3.12 g, 0.01 mol) in acetyl chloride (35 mL,
0.5 mol) for 2 h, followed by distilling off the excess acetyl chloride
afforded a yellow solid which upon recrystallization gave the anhydride 3
(cf. Table 1).
IR spectrum of 3 showed the carbonyl absorption bands at 1725 and
1790 cmÀ1 characteristic for six-membered ring anhydride fused aromatic
1
system.10 The H-NMR (DMSO-d6) of 3: d 6.39 (s, 2H, O-CH2-O), 7.51
(s, 1H, HC¼C), 7.75–8.19 (m, 4H, Ar-H), 8.59–8.84 (m, 3H, Ar-H of piper-
onyl moiety). The MS of 3: 294 (20), 264 (8), 249 (6), 257 (4), 221 (12),
192 (30), 180 (8), 163 (100), 152 (18), 137 (16), 129 (22), 111 (19), 101 (60),
87 (80), 75 (82), 63 (72) and 50 (37).
Action of Aluminium Chloride upon the Anhydride 3; Formation
of 2-(2-Carboxyphenyl)-5,6-methylenedioxyind-2-enone 4
To a solution of the anhydride 3 (2.94 g; 0.01 mol) in excess acetylene
tetrachloride (50 mL), anhydrous aluminium chloride (1.6 g; 0.012 mol)
was added dropwise and the reaction mixture was stirred for 15 h at
room temperature, left to stand overnight and hydrolyzed with ice-cold
dilute hydrochloric acid. The solvent was removed by steam distilla-
tion and the product was taken up in ether, washed with Na2CO3 solution
(10%). The alkaline extract on acidification afforded the oxoacid 4
(cf. Table 1).
IR spectrum of 4 exhibited nC¼O at 1690 and 1700 cmÀ1 for aryl acid
and ring ketonic functions.10 1H-NMR (CDCl3) of 4 exhibited the following
signals: d 6.42 (s, 2H, O-CH2-O), 7.42–8.18 (m, 5H, Ar-H), 8.81 (s, 1H,
Ar-H of piperonyl moiety), 8.98 (s, 1H, Ar-H of piperonyl moiety) and

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SYNTHESIS OF NEW HETEROCYCLIC SYSTEMS
399
10.81 (s, 1H, COOH). The MS of 4: 294 (38), 250 (100), 220 (20), 173 (14),
148 (3), 120 (46) and 77 (65).
Action of 1-Naphthylamine on the Cyclic Anhydride 3;
Formation of 2-[N-(1-Naphthyl)carboxamido]-3,4-
methylenedioxybenzylidinephenylacetic Acid 5
A solution of 3 (2.94 g; 0.01 mol) and 1-naphthylamine (1.43 g;
0.01 mol) in 50 mL of benzene was refluxed for 4 h. Most of the solvent
was distilled off and the solid that separated out after cooling was collected
by suction and recrystallized from suitable solvent to give 5 (cf. Table 1).
IR spectrum of 5 exhibited two absorption bands at 1668 and
1703 cmÀ1 characteristic for nC¼O (amide) and nC¼O (a,b-unsaturated
1
acid). The H-NMR (CDCl3) of 5 exhibited the following signals: d 6.46
(s, 2H, O-CH2-O), 7.48 (s, 1H, HC¼C), 7.63–8.28 (m, 11H, Ar-H),
8.45–8.77 (m, 3H, Ar-H of piperonyl moiety) and 10.77 (s, 1H, COOH).
The MS of 5: 437 (61), 419 (32), 393 (8), 315 (24), 267 (20), 251 (12), 222
(100), 170 (12), 143 (9) and 77 (37).
Reaction of N-(1-Naphthyl)-3,4-methylenedioxybenzylidine
Homophthalamic Acid 5 with Acetic Anhydride and Perchloric Acid;
Formation of N-(1-Naphthyl)-3,4-methylenedioxybenzylidine
Homophthalisoimidium Perchlorate 6
Perchloric acid (10 mL) was slowly added for 15 min to a suspension of
5 (4.37 g; 0.01 mol) in freshly distilled acetic anhydride (100 mL) kept in an
ice bath. The solid salt that precipitated was collected by filtration, washed
with petroleum ether (60–80ꢀC), dried and recrystallized from the proper
solvent to afford 6 (cf. Table 1).
IR spectrum of 6 was found to be consistent with the proposed
structure. Thus compound 6 displayed nC¼O at 1830 cmÀ1 together with
1
strong absorption band at 1662 cmÀ1 (nC¼Nþ). The H-NMR (DMSO-d6)
of 6: d 6.39 (s, 2H, O-CH2-O), 6.27–7.95 (m, 12H, Ar-H andÈHC¼C),
8.50–8.78 (m, 3H, Ar-H of piperonyl moiety) and 9.00 ðs, 1H, ¼N HÞ.
j

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AZAB, MADKOUR, AND MAHMOUD
Reaction of 6 with Active Methylene Containing Compounds
Namely: Ethyl Acetoacetate, Ethyl Cyanoacetate, andDiethyl
Malonate; Formation of the Lactams 7a–c
A solution of 6 (5.19 g; 0.01 mol) in pyridine (30 mL) was stirred with
the appropriate active methylene compound (0.1 mol) at room temperature
for 1 h. The reaction solution was left overnight, then, cold hydrochloric
acid was added with stirring. The solid that deposited down was collected by
filtration and recrystallized from the suitable solvent (cf. Table 1).
IR spectrum of 7 showed one carbonyl absorption band at ca. 1685–
1
1672 (6-membered lactam). The H-NMR (DMSO-d6) of 7b: d 1.66 (t, 3H,
CH2CH3), 3.97 (q, 2H, CH2CH3), 6.42 (s, 2H, O-CH2-O), 6.27–7.85 (m, 12H,
Ar-H and HC¼C) and 8.42–8.57 (m, 3H, Ar-H of piperonyl moiety).
Reaction of 6 with GrignardReagents; Formation of
Aralkyl-2-[N-(1-naphthyl)carboxamido]-3,4-
methylenedioxybenzylidinebenzyl Ketone 8a–c
A solution of the appropriate Grignard’s reagent (0.3 mol) in dry ether
(50 mL) was added dropwise to a solution of 6 (5.19 g; 0.01 mol) in dry ether
(50 mL) with occasional shaking. The reaction mixture was refluxed for 6 h
on water bath, then left overnight and decomposed with saturated aqueous
ammonium chloride solution. The organic layer was separated then evapo-
rated to afford the crude solid product which recrystallized to afford 8
(cf. Table 1).
IR spectra of 8 showed two absorption bands for the carbonyl stretching
frequencies of ketones and amides at ca. 1695 and 1662 cmÀ1 as well as nNH
1
of amides at ca. 3310 cmÀ1. The H-NMR (DMSO-d6) of 8a exhibited the
following signals: d 4.06 (s, 2H, -CH2C6H5), 5.57 (s, 1H, -NH), 6.42 (s, 2H, O-
CH2-O), 7.54 (s, 1H, HC¼C) and 7.72–7.93 (m, 5H, Ar-H of benzyl moiety),
8.10–8.33 (m, 11H, Ar-H) and 8.42–8.57 (m, 3H, Ar-H of piperonyl moiety).
Reaction of 6 with Aromatic Hydrocarbons; Formation
of Hydroxy-3,4-methylenedioxybenzylidine
Homophthalimidine Derivatives 9a–c
To a stirred cold solution or suspension of 6 (5.19 g; 0.01 mol) in
aromatic hydrocarbon (50 mL), anhydrous AlCl3 (0.03 mol) was added por-
tionwise. The mixture was, then stirred for 5 h at room temperature and left
overnight, then, hydrolyzed with ice cold hydrochloric acid. The resulting

ORDER
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SYNTHESIS OF NEW HETEROCYCLIC SYSTEMS
401
organic product was filtered off, washed with cold water, dried and crystal-
lized from the proper solvent to give 9 (cf. Table 1).
IR spectra of 9 exhibited one carbonyl absorption band at
ca. 1674–1660 cmÀ1 and a broad band at 3100–3460 cmÀ1 (nOH). The
1H-NMR (DMSO-d6) of 9b exhibited the following signals: d 3.27 (s, 3H,
OCH3), 5.81 (s, 1H, OH), 6.45 (s, 2H, O-CH2-O), 7.69 (s, 1H, HC¼C) and
7.80–8.54 (m, 18H, Ar-H).
Reaction of 6 with Primary Aromatic Amines; Formation
of N,N0-Disubstituted-3,4-methylenedioxybenzylidine
Homophthalamide 10a–e
Compound 6 (5.19 g; 0.01 mol) was added to a stirred solution of the
appropriate amine (0.01 mol) namely, aniline, p-toluidine, p-anisidine,
p-chloroaniline and benzylamine in benzene (30 ml). The reaction mixture
was then stirred for one hour at room temperature. Excess solvent was
distilled off to afford a solid product which on recrystallization from suitable
solvent gave 10a–e (cf. Table 1).
IR spectra of 10 exhibited nC¼O at 1652–1636 cmÀ1 (amide) and nNH at
1
3250–3152 cmÀ1. The H-NMR (DMSO-d6) of 10b showed the following
signals: d 2.00 (s, 3H, CH3), 5.54 (s, def., 2H, 2NH), 6.42 (s, 2H, O-CH2-O),
7.69 (s, 1H, HC¼C) and 7.81–8.54 (m, 18H, Ar-H).
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Received in the USA March 19, 2001

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