Synthesis and studies of some new fused/spiro heterocyclic compounds containing nitrogen and sulfur

Article abstract of DOI:10.1080/10426500701841821

Spiro β-lactam, thiazolidinone derivatives, fused pyrazolo, pyrimidino, pyrimidinthion, and Isoxazolo incorporating new compound 2 has been synthesized by cyclocondensation addition reaction and cycloaddition reaction of monochloroacetyl chloride, mercapt

Full text of DOI:10.1080/10426500701841821

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Phosphorus, Sulfur, and Silicon
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Synthesis and Studies of Some
New Fused/Spiro Heterocyclic
Compounds Containing
Nitrogen and Sulfur
N. A. A. Elkanzi a
a Chemistry Department, Faculty of Science , South
Valley University , Aswan, Egypt
Published online: 28 Jul 2008.
To cite this article: N. A. A. Elkanzi (2008) Synthesis and Studies of Some
New Fused/Spiro Heterocyclic Compounds Containing Nitrogen and Sulfur,
Phosphorus, Sulfur, and Silicon and the Related Elements, 183:8, 2040-2057, DOI:
10.1080/10426500701841821
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Phosphorus, Sulfur, and Silicon, 183:2040–2057, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500701841821
Synthesis and Studies of Some New Fused/Spiro
Heterocyclic Compounds Containing Nitrogen and Sulfur
N. A. A. Elkanzi
Chemistry Department, Faculty of Science, South Valley University,
Aswan, Egypt
Spiro β-lactam, thiazolidinone derivatives, fused pyrazolo, pyrimidino, pyrim-
idinthion, and Isoxazolo incorporating new compound 2 has been synthesized by
cyclocondensation addition reaction and cycloaddition reaction of monochloroacetyl
chloride, mercaptoacetic acid, hydrazinehydrate, phenylhydrazine, urea, thiourea,
and hydroxyl amine hydrochloride.
Keywords Mercaptoacetic acid; oxazole; pyrazole; pyrimidine; pyrimidintion; schiff
bases; spiro β-lactams; Spiro thiazolidinone
INTRODUCTION
A large number of penicillins are known and used as potent
antibiotics,1 β-lactams and related derivatives have been found to
be active compounds having antibacterial activities. Some examples
comprise the naturally occurring monobactams and nocardicins.2 Con-
trary to penicillins, cephalosporins, or nocardicins, monobactams were
not produced by fungi or actinomycetes, but from bacteria, for exam-
ple Bacillus, pseudomonas.3 The synthetic oxamazine,4–6 thiamazins,7
and monosulfactams8 showed some antibacterial activity, which raised
again a major interest in the area of 2-azetidinone chemistry. Also, thi-
azole derivatives such as penicillin, which has fused thiazolidine and
β-lactam rings were known and used as potent antibiotics.9 Thiazole
derivatives are also associated with a broad spectrum of biological prop-
erties, including anticonvulsant,10,11 antimicrobial,12–14 antitubercu-
lar, and bacteriostatic activities.15,16 Therefore, compounds containing
β-lactam ring, thiazolidinone are expected to possess potential
Address correspondence to N. A. A. Elkanzi, Chemistry Department, Faculty of Sci-
ence, South Valley University, Aswan, Egypt. E-mail: kanzi2nour@yahoo.com
2040

New Fused/Spiro Heterocyclic Compounds
2041
biological activities. Our previous work aimed at developing new ap-
proaches to the synthesis of polyfunctionally substituted heterocyclic
compounds of biological activity.17–19 Also pyrazoles, oxazole, pyrim-
idinethione, thioglycolic and β-lactam derivatives play a vital role in
many biological processes20–24 and as synthetic drugs. The chemistry
of these heterocyclic compounds has received much attention in recent
years. This is principally due to the unique physical and chemical prop-
erties of such compounds, which enable their wide application as plant
growth regulators,25 dyes,26 and corrosion inhibitors.27
RESULTS AND DISCUSSION
The new compound 2 was synthesized by the reaction of 4-amino-
2-methyl-5,10-dioxo-1,5,10,11-tetrahydrobenzo[g]quinoline-3- carboni-
trile 1, which was prepared according to a reported method,18 with
equimolar ratios of mercaptoacetic acid in dry pyridine. The activity of
methyl group at C2 renders it available to react with mercaptoacetic
acid through elimination of a molecule of water followed by cycliza-
tion to give compound 2. Thus, compound 2 was prepared according to
Equation (1). Structure 2 was preferred over possible 2ꢀ based on ele-
mental analysis, IR, 1H NMR spectrum of the product in DMSO showed
singlet at δ 2.81 for 2H and singlet at δ 2.35 for 2H supporting the struc-
ture of compound 2 and mass spectral data showed the molecular ion
peak at m/z (337). The reaction of compound 1 with mervaptoacetic
acid is considered the oxidative cyclization involving the conversion of
an amine and a thiol to a sulfenamide.28,29
Our approach to the synthesis of the desired spiro compounds started
with compounds 3a–c, which were prepared by the condensation of ni-
troso compounds such as α-nitroso β-naphthol, p-nitrosophenol, and
p-nitroso-N-dimethylaniline with compound 2 in ethanol using a piperi-
dine catalyst, which afforded the new Schiff bases compounds.
The structure of these newly synthesized Schiff bases compounds
3a–c were confirmed by elemental analysis and infrared spectra, which
showed absorption bands at 1620–1580 cm−1 attributed to C N and a
characteristic band attributed to C O at 1700–1696 cm−1 and 3310
attributed to NH2.30
The formation of Schiff bases 3a–c is expected to owing suggested
mechanism, (c.f. Equation [2]).
The first step in the previous mechanism involves the formation of
carboanion (a) using piperidine as a catalyst, which abstracted a proton
from the active hydrogen center; accordingly, it was added itself on
the polarized aromatic nitroso compounds forming the intermediate
compound (b) to uptake a proton from the piperidinium ion forming

2042
N. A. A. Elkanzi
(1)
compound (c). The latter compound (c) lost a mole of water to produce
the Schiff base compound 3a–c.
Compound 3a–c underwent cycloaddition with chloroacetyl chloride
to give spiro lactam 4a–c. The cycloaddition proceeded smoothly in dry
xylene in the presence of a triethylamine catalyst19,31 to afford 4a–
c. The reaction of compound 3a–c with chloroacetyl chloride proceeded
through a [2 + 2] cycloaddition; the cycloaddition reaction was assumed
to go through the following suggested mechanism (c.f. Equation [3]).
The structure of spiro lactams 4a–c confirmed by analytical data
and infrared spectra, which showed the disappearance of the absorp-
tion band of C N at 1580 cm−1, also showed a C-N absorption band
1
at 1225 cm−1 and C O of a β-lactam ring at 1765 cm−1 and H NMR
spectrum, which showed signals at δ 6.65 (s, NH2), multiplet signals at
δ 8–7 for aromatic protons, at δ 4.22 singlet for β-lactam carbon proton,
at δ 2.56 (s, S-CH2).

New Fused/Spiro Heterocyclic Compounds
2043
(2)
Spirothiazolidinone 5a–c was prepared by the cycloaddition of mer-
captoacetic acid (1:1 molar ratios) in dioxane in the presence of triethy-
lamine as catalyst was heated under reflux on a steam bath for 15 h.
and afforded the corresponding compound 5a–c. The cycloaddition re-
action was assumed to go through the following suggested mechanism
(c.f., Equation [4]).
The structure of thiazolidinone derivatives 5a–c was identified from
the correct elemental analysis and infrared spectra, which showed an
1
absorption band at 1680–1640 cm−1 attributed to C O group and H-
NMR spectrum, which showed a singlet signal at 2.45 for CH2 of the
thiazolidinone ring.

2044
N. A. A. Elkanzi
(3)
The activity of carbonyl group in compound 2 lead compound 2 was
easily condensed with different aromatic amine in dry DMF and few
drops of piperidine as a catalyst to give new Schiff bases derivatives
6a–c. The structure of compound 6a–c were confirmed by elemental
analysis and infrared spectra, which showed absorption bands at 1625–
1580 cm−1 attributed to C N and a characteristic band attributed to
C O at 1710–1699 cm−1 and 3310 attributed to NH2.28
The formation of Schiff bases 6a–c is expected to using the same
suggested mechanism of compound 3a–c.
Compound 6a–c underwent cycloaddition with chloroketene to give
spiro lactam 7a–c. The cycloaddition proceeded smoothly in toluene
in the presence of a triethyl amine catalyst19,29 to afford 7a–c. The
formation of newly spiro thiazolidinone 7a–c is expected to owing the
same suggested mechanism of compound 4a–c. The structure of spiro
lactams 7a–c confirmed by analytical data and infrared spectra, which
showed the disappearance of the absorption band of C N at 1580 cm−1
,
also showed a C-N absorption band at 1527 cm−1 and C O of a β-lactam
1
ring at 1760 cm−1 and H-NMR spectrum, which showed signals at δ
6.69 (s, NH2), multiplet signals at δ 8–7 for aromatic protons, at δ 4.25
singlet for β-lactam carbon proton, at δ 2.52 (s, S-CH2).

New Fused/Spiro Heterocyclic Compounds
2045
(4)
Spiro thiazolidinone 8a–c was prepared by the cycloaddition of mer-
captoacetic acid in dioxane in the presence of triethyl amine as a
catalyst was heated under reflux for 15 h. and afforded the corre-
sponding compound 8a–c, the cycloaddition reaction was assumed to
go through the same suggested mechanism of formation of compound
5a–c.
The structure of thiazolidinone derivatives 8a–c was identified from
the correct elemental analysis and infrared spectra, which showed an
1
absorption band at 1685–1645 cm−1 attributed to C O group and H-
NMR spectrum, which showed a singlet signal at 2.39 for CH2 of the
thiazolidinone ring.
The activity of the methylene group in compound 2 lead compound 2
was easily condensed with different aromatic aldehydes in ethanol as
a solvent using piperidine catalyst to give 9a–c. The structure of com-
pound 9a–c was confirmed by elemental analysis and IR, which re-
vealed the presence of peak NH2 at 2300–3100 cm−1, C O 1725–1670
cm−1, and C C 1610–1585 cm−1; also, its structures were confirmed by
1H-NMR and mass spectral data (c.f. Tables I and II).
The activity of the exocyclic group C C in compound 9a–c in conju-
gation with the carbonyl group was demonstrated by a reaction with hy-
drazines, hydroxylamine hydrochloride, urea, and thiourea. The nature
of the structure of the products for the previously mentioned reaction,
according to the different methods of analysis, elemental analysis, IR,
and mass spectra, gave us the agreements that the reaction is carried
out by condensation addition reaction through the α, β-unsaturated ke-
tonic system. Thus, the chemical work covers the implementation of the
following fused heterocyclic compounds and the details are as follows
(c.f. Equation [4]).

2046

2047

2048

2049

2050

2051

2052
N. A. A. Elkanzi
(5)
N-acetyl (phenyl) derivatives of compounds 10a–c and 11a–c were
synthesized by the interaction of 9a–c with equimolecular ratios of hy-
drazine hydrate or phenylhydrazine in the presence of glacial acetic
acid and piperidine as a catalyst, respectively.
The structures of 10a–c and 11a–c were confirmed by elemental
analysis, IR, 1H NMR, and mass spectra (c.f. Tables I and II). The struc-
ture of compound 10a was confirmed by elemental analysis, IR, and an
1H NMR spectrum, which revealed the presence of singlet signal at
δ 6.65 for NH2 and a multiplet signal at δ 8–7 for aromatic protons, at
δ 2.56 (s, CH3), δ 2.45 (s, CH2-S), δ 2.23 (d, CH), δ 1.65 (d, CH), and
mass spectral data showed the molecular ion peak at m/z (481). Also,
the structure of compound 11a was confirmed by elemental analysis,
1
IR, and an H NMR spectrum, which revealed the presence of singlet
signal at δ 6.67 for NH2 and a multiplet signal at δ 8–6 for aromatic
protons, at δ 2.49 (s, CH2S), δ 1.61 (d, CH), and δ 1.12 (d, CH), and mass
spectral data showed the molecular ion peak at m/z (515).
Isoxazolino derivatives of compounds 12a–c were synthesized by the
reaction of 9a–c with equimolecular ratios of hydroxylamine hydrochlo-
ride in the presence of sodium hydroxide [c.f. Equation (5)]. The struc-
tures of 12a–c were confirmed by elemental analysis, IR, 1H-NMR, and
mass spectra (c.f. Tables I and II).
Pyrimidine and pyrimidinethion derivatives of compounds 13a–c
and 14a–c were synthesized by the reaction of 9a–c with equimolec-
ular ratios of urea and/or thiourea in ethanol containing 20 ml of hy-
drochloric acid and/or in the presence of sodium hydroxide, respectively
[c.f. Equation (6)]. The structures of compounds 13a–c and 14a–c were
confirmed by analytical and spectral analysis (c.f. Tables I and II).

New Fused/Spiro Heterocyclic Compounds
2053
(6)
EXPERIMENTAL
Melting points were uncorrected and determined using Kofler m.p.
apparatus. IR spectra were recorded on a Pye Unicam SP3-100 spec-
1
trophotometer using the KBr water technique. H NMR spectra were
recorded on a Varian EM-39090 MHz spectrometer using TMS as an
internal standard. MS spectra were measured on SSQ-7000 apparatus
at 70 eV. Elemental analyses were carried out at the Microanalytical
center of Cairo University (Cairo, Egypt) and at the Microanalytical
Unit at Assiut University (Assiut, Egypt). The characterization data of
all newly synthesized compounds are given in Tables I and II.

2054
N. A. A. Elkanzi
4-Amino-2-methyl-5,10-dioxo-1,5,10,11-
tetrahydrobenzo[g]quinoline-3-carbonitrile 1
This compound was prepared according to a reported method.18
The Synthesis of New Compound 2
A mixture of 1 (2.65 g, 0.01 mmol) and mercaptoacetic acid (0.92 g,
0.01 mmol) in dry pyridine (20 ml) was heated under reflux on a steam
bath for 13 h. The solid product that separated after cooling was col-
lected and recrystallized from the proper solvent to give 2 as green
crystals.
The Synthesis of New Schiff Bases Derivatives 3a–c
A mixture of 2 (3.37 g, 0.01 mmol), aromatic nitroso compounds
(0.01 mmol), and a few drops of piperidine (0.5 ml) in ethanol (15 ml)
was heated under reflux for 8 h, concentrated, and allowed to cool. The
precipitate that formed was collected and recrystallized from the proper
solvent to give 3a–c.
The Synthesis of Spiro Lactam Derivatives 4a–c
A mixture of 3a–c (0.01 mmol) and chloroacetyl chloride (1.13 g,
0.01 mmol) in dry xylene (30 ml) and triethylamine (0.01 ml) as cat-
alyst was heated under reflux for 14 h. The solid that separated up on
cooling was filtered off and crystallized from the proper solvent to give
4a–c.
The Synthesis of Spiro Thiazolidinone Derivatives 5a–c
A mixture of 3a–c (0.01 mmol), mercaptoacetic acid (0.92 g, 0.01 mmol)
and triethylamine (0.01 ml) in dioxane (20 ml) was heated under reflux
on a steam bath for 15 h. The solid product that separated after cooling
was collected and recrystallized from the proper solvent to give 5a–c.
The Synthesis of Schiff Bases Derivatives 6a–c
A mixture of 2 (3.37 g, 0.01 mmol) aromatic amine (0.01 mmol), and few
drops of piperidine (0.5 ml) in dry DMF (30 ml) was heated under reflux
for 7 h. the solvent was then evaporated under reduced pressure, and
the residue was treated with ice water. The solid product was collected
and crystallized from the proper solvent to give 6a–c.

New Fused/Spiro Heterocyclic Compounds
2055
The Synthesis of New Spiro Lactam Derivatives 7a-c
A mixture of 6a–c (0.01 mmol), chloroacetyl chloride (1.13 g, 0.01 mmol)
in toluene (20 ml) and triethylamine (0.01 ml) was heated to reflux
under magnetic stirring for 12 h. Concentration in vacuo gave a residue,
which was taken up in acetone and chromatographed on silica gel plates
(cyclohexane 7/ethyl acetate 7.5) to afford a crude material, which was
crystallized from the proper solvent to give 7a–c.
Synthesis of New Spiro Thiazolidinone Derivatives 8a–c
A mixture of 6a–c (0.01 mmol), mercaptoacetic acid (0.92 g, 0.01 mmol)
in dioxane (30 ml) and triethyl amine catalyst (0.01 mmol) was stirred
under reflux for 15 h. Concentration in vacuo afforded a crude material,
which was dissolved in ethylacetate and chromatographed on silica gel
(hexane 4/ethyl acetate 1) to give a solid substance, which was crystal-
lized from the proper solvent to give 8a–c.
Synthesis of Arylidene Compound Derivatives 9a–c
To a mixture of 2 (3.37 g, 0.01 mmol) and different aromatic aldehyde
(0.01 mmol) in absolute ethanol (20 ml) was added piperidine (5 drops).
The mixture was heated under reflux for 6 h. the crystalline product
thus obtained after cooling was collected and recrystallized from the
proper solvent to give 9a–c.
The Reaction of Compound 9a–c with Hydrazine Hydrate
to Give N-Acetyl-pyrazolo Derivatives 10a–c
A magnetically stirred mixture of compound 9a–c (0.01 mmol) and hy-
drazine hydrate (0.50 g, 0.01 mmol) in ethanol (30 ml) in the presence of
glacial acetic acid and piperidine as a catalyst was heated to reflux for
10 h. On cooling to room temperature, the precipitate was collected and
boiled with petroleum ether (60–80◦C). The residue was treated with
ice water, and the solid obtained was collected and crystallized from the
proper solvent to give 10a–c.
The Reaction of Compound 9a–c with Phenylhydrazine
to Give N-phenylhydrazine to Give N-phenyl-pyrazolo
Derivatives11a–c
A mixture of 9a–c (0.01 mmol) and phenylhydrazine (1.08 g, 0.01 mmol)
in dry DMF (30 ml) in the presence of a catalytic amount of piperidine

2056
N. A. A. Elkanzi
(0.1 ml) was heated under reflux on a steam bath for 14 h. The sol-
vent was then evaporated under reduced pressure, and the residue was
treated with cold water. The solid product was collected and crystallized
from the proper solvent to give 11a–c.
The Reaction of Compound 9a–c with Hydroxylamine
Hydrochloride to Give Isoxazolo Derivatives 12a–c
A mixture of 9a–c (0.01 mmol) in absolute ethanol (20 ml) was treated
with hydroxylamine hydrochloride (0.69 g, 0.01 mmol) in the presence of
sodium hydroxide as a catalyst. The reaction mixture was heated under
reflux for 13 h. The reaction mixture was filtered hot. The solvent was
then evaporated under reduced pressure, and the remaining resin was
boiled with petroleum ether (60–80◦C). The solid product was collected
and crystallized from the proper solvent to give 12a–c.
The Reaction of Compound 9a–c with Urea to Give Pyrimidino
Derivatives 13a–c
A mixture of 9a–c (0.01 mmol) and urea (0.60 g, 0.01 mmol) in ethanol
(30 ml) was added Conc. HCl (20 ml). The mixture was heated under
reflux for 15 h. It was then filtered hot and allowed to cool; the sol-
vent evaporated under reduced pressure, and the residue was treated
with crushed ice and neutralized with 5N NaOH. The solid product was
collected and crystallized from the proper solvent to give 13a–c.
The Reaction of Compound 9a–c with Thiourea to Give
Thio-pyrimidino Derivatives 14a–c
A mixture of 9a–c (0.01 mmol) and thiourea (0.76 g, 0.01 mmol) in dry
DMF (20 ml) was added sodium hydroxide as catalyst. The reaction
mixture was heated under reflux for 13 h. It was then filtered hot; the
solvent evaporated under reduced pressure to dryness, and the residue
treated with petroleum ether (60–80◦C). The excess of petroleum ether
was removed, and the residue was treated with cold water. The solid
product was collected and crystallized from the proper solvent to give
14a–c.
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New Fused/Spiro Heterocyclic Compounds
2057
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