Synthesis and studies of some nitrogen and sulfur compounds

Article abstract of DOI:10.1080/10426500210672

Pyrazolo-, pyrimidino-, isoxazolo-, thiozolo-, and β-lactam incorporating thienopyridazine has been synthesised by cyclocondensation addition reaction and cycloaddition reaction of hydrazine hydrate phenyl hydrazine, hydroxylamine hydrochloride, urea, thiourea, mercapto acetic acid and monochloroacetyl chloride.

Full text of DOI:10.1080/10426500210672

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Phosphorus, Sulfur, and Silicon and the Related
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Synthesis and Studies of Some Nitrogen and Sulfur
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H. A. Soleiman a , F. M. Abd El-Latif a , M. A. Khalil a & I. H. Elazab a
a Chemistry Department, Aswan-Faculty of Science, South Valley University, Aswan, Egypt
Available online: 27 Oct 2010
To cite this article: H. A. Soleiman, F. M. Abd El-Latif, M. A. Khalil & I. H. Elazab (2002): Synthesis and Studies of Some
Nitrogen and Sulfur Compounds, Phosphorus, Sulfur, and Silicon and the Related Elements, 177:4, 1001-1014
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Phosphorus, Sulfur and Silicon, 2002, Vol. 177:1001–1014
C
Copyright 2002 Taylor & Francis
1042-6507/02 $12.00 + .00
SYNTHESIS AND STUDIES OF SOME NITROGEN
AND SULFUR COMPOUNDS
H. A. Soleiman, F. M. Abd El-Latif, M. A. Khalil,
and I. H. Elazab
Chemistry Department, Aswan-Faculty of Science,
South Valley University, Aswan, Egypt
(Received June 2, 2001; accepted October 23, 2001)
Pyrazolo-, pyrimidino-, isoxazolo-, thiozolo-, and -lactam incorpo-
rating thienopyridazine has been synthesised by cyclocondensation
addition reaction and cycloaddition reaction of hydrazine hydrate
phenyl hydrazine, hydroxylamine hydrochloride, urea, thiourea, mer-
capto acetic acid and monochloroacetyl chloride.
Keywords: Nitrogen; pyrazolo; sulfur
INTRODUCTION
A five and six membered heterocyclic systems containing nitrogen-,
oxygen-, and sulfur atoms of fused and spiro pyrazolo-, pyrimidino-,
isoxazolo-, thiazolo-, and -lactam incorporating thienopyridazine were
5
found to possess interesting biological properties1 and as synthetic
10
drugs.6
The chemistry of these heterocyclic compounds has received
much attention in recent years. This principally due to the unique
physical and chemical properties of such compounds, which enable
their wide application as plant growth regulators.11 Recently, we have
reported the synthesis and structure activity relationship of variety
heterocyclic and aromatic derivatives of theinopyridazines.12,13 In our
screening substances showing interesting biological activity and un-
usual chemical structures have been detected. The molecules described
in this work are composed of a five-, and six-membered heterocyclic
systems containing nitrogen-, oxygen-, and sulfur atoms. However
various styryl compounds and Schiff base compounds incorporating
the theinopyridazine residue we have been synthesized and studies.
Address correspondence to H. A. Soleiman, Department of Chemistry, Aswan-Faculty
of Science, South Valley University, Aswan, Egypt.
1001

1002
H. A. Soleiman et al.
Therefore, several fused and spiro pyrazolo-, pyrimidino-, isoxazolo-,
thiazolo-, and -lactam derivatives are synthesized and tested for bio-
logical activity.
RESULTS AND DISCUSSION
Acetylation of aminotheinopyridazine derivative (1) with one mole
equivalent of acetic anhydride yielded the corresponding acety-
laminotheinopyridazine derivative (2).14
Synthesis of chalcone compound derivatives (3a–e) were achieved
through the interaction of the theinopyridazine (2) with aromatic
aldehydes such as p. hydroxybenzaldehyde -nitrobenzaldehyde, ben-
zaldehyde, -N-dimethylbenzaldehyde and -chlorobenzaldehyde us-
ing piperidine as catalyst in the presence of ethanol as solvent af-
forded chalcone compound dervative 3a–e. The structure of 3a–e were
confirmed by Microanalysis data, Mass spectra, Infrared spectra and
1H NMR spectra (c.f. Tables I and II).
The chalcone compound derivatives 3a–f when interacted with one
mole of hydrazine hydrate in presence of acetic acid, and one mole
of phenyl hydrazine under piperidine catalyzed, gave the required
N-acetyl-, and N-phenyl-, pyrazolo derivatives (4a–e and 5a–e) respec-
tively, (Scheme 1). The structure of (4a–e and 5a–e) were confirmed
1
by Microanalysis data, Mass spectra, Infrared spectra and H NMR
spectra (c.f. Tables I and II).

Synthesis and Studies
1003
SCHEME 1
Synthesis of isoxazolo compound derivatives (6a–e) were achieved
through the interaction of chalcone compound derivatives (3a–e) with
one mole of hydroxylamine hydrochloride in ethanol as organic solvent
under effect of sodium hydroxide as catalyst formed isoxazolo compound
derivatives 6a–e, Scheme (1). The structure of (6a–e) were confirmed by
Microanalysis data, Mass spectra, Infrared spectra and 1H NMR spec-
tra (c.f. Tables I and II). Also, synthesis of pyrimidines compound deriva-
tives (7a–e and 8a–e), were achieved through the interacted of chalcone
compound derivatives (3a–e) with one mole of urea in ethanol as solvent

1004

1005

1006

Synthesis and Studies
1007
TABLE II Selected IR, 1H NMR Spectra Data for the New Compounds
Listed in Table I
Compound
1
no.
IR (cm
)
1H NMR (ppm)
3a
3b
3c
3d
3e
3274 (OH), 3133 (NH), 1702 (C
ester), 1654 (C O amide),
1540 (C N)
O
1.3 (t, 3H, J = 7.2 Hz), 2.7 (s, 1H),
4.4 (q, 2H, J = 7.2 HZ), 6.20 (d,
1H, J = 15.90 H2), 6.40 (d, 1H,
J = 15.90 H2), 7.46–7.57 (m, 9H),
7.92 (s, 1H), 11.06 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.20 (d, 1H, J = 15.9),
6.40 (d, 1H, J = 15.9 Hz), 7.46–
7.57 (m, 9H), 7.92 (s, 1H), 11.06
(s, 1H).
3150 (NH), 1750 (C O ester),
1670 (C O amide),
1555 (C N)
3140 (NH), 1725 (C O ester),
1680 (C O amide), 1550
(C N)
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.20 (d, 1H,
J = 15.90 Hz), 6.40 (d, 1H,
J = 15.90 Hz), 7.46–7.57 (m, 10H),
7.92 (s, 1H), 11.06 (s, 1H).
3155 (NH), 1710 (C O ester),
1650 (C O amide), 1525
(C N)
1.2 (m, 6H), 1.4 (t, 3H, J = 7.2 Hz),
4.4 (q, 2H, J = 7.2 Hz), 6.20
(d, 1H, J = 15.90 Hz), 6.40 (d, 1H,
J = 15.90 Hz), 7.46–7.57 (m, 9H),
7.92 (s, 1H). 11.06 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.20 (d, 1H, J = 15.90
Hz), 6.40 (d, 1H, J = 15.90 Hz),
7.46–7.57 (m, 9H), 7.92 (s, 1H),
11.06 (s, 1H),.
3150 (NH), 1699 (C O ester),
1660 (C O amide), 1530
(C N)
4a
4b
4c
4d
4e
3260 (OH), 3120 (NH),
1700 (C O ester), 1690 (C
ketone), 1540 (C N)
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 3.5 (s, 3H), 6.60 (s,
1H), 7.50–7.60 (m, 9H), 7.94 (s,
1H), 11.00 (s, 1H), 11.05 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 3.5 (s, 3H),
4.4 (q, 2H, J = 7.2 Hz), 6.60 (s, 1H),
7.50–7.60 (m, 9H), 7.94 (s, 1H),
11.05 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 3.5 (s, 3H),
4.4 (q, 2H, J = 7.2 Hz), 6.60 (s,
1H), 7.46–7.57 (m, 10H), 7.92
(s, 1H), 11.06 (s, 1H).
1.2 (m, 6H), 1.4 (t, 3H, J = 7.2 Hz),
3.5 (s, 3H), 4.4 (q, 2H, J = 7.2 Hz),
6.55 (s, 1H), 7.43–7.58 (m, 9H),
7.90 (s, 1H), 11.00 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 3.5 (s, 3H), 4.4
(q, 2H, J = 7.2 Hz), 6.60 (s, 1H),
7.46–7.57 (m, 9H), 7.92 (s, 1H),
11.00 (s, 1H).
O
3113 (NH), 1709 (C O ester),
1699 (C O ketone), 1561
(C N)
3145 (NH), 1705 (C O ester),
1700 (C O ketone), 1570
(C N)
3140 (NH), 3400 (NH),
1720 (C O ester), 1690 (C
ketone), 1540 (C N)
O
3130 (NH), 1739 (C O ester),
1680 (C O keton) 1555 (C N)
(Continued on next page)

1008
H. A. Soleiman et al.
TABLE II Selected IR, 1H NMR Spectra Data for the New Compounds
Listed in Table I (Continued)
Compound
1
no.
IR (cm
)
1H NMR (ppm)
5a
3300 (OH), 3110 (NH),
1750 (C O ester), 1690
(C O ketone), 1550 (C N)
1.3 (t, 3H, J = 7.2 Hz), 2.7 (br, 1H),
4.4 (q, 2H, J = 7.2 Hz), 6.65 (s, 1H),
7.45–7.58 (m, 14H), 7.95 (s, 1H),
11.08 (s, 1H).
5b
5c
5d
3100 (NH), 1765 (C O ester),
1710 (C O ketone), 1530
(C N)
3115 (NH), 1750 (C O ester),
1715 (C O ketone), 1515
(C N)
3225 (NH), 1746 (C O ester),
1720 (C O ketone), 1520
(C N)
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H, J =
7.2 Hz), 6.65 (s, 1H), 7.45–7.58 (m,
14H), 7.95 (s, 1H), 11.08 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H, J =
7.2 Hz), 6.65 (s, 1H) 7.45–7.58 (m,
15H), 7.95 (s, 1H), 11.08 (s, 1H).
1.2 (m, 6H), 1.4 (t, 3H, J = 7.2 Hz),
4.4 (q, 2H, J = 7.2 Hz), 6.65 (s,
1H), 7.45–7.58 (m, 14H), 7.95 (s,
1H), 11.08 (s, 1H).
5e
6a
3220 (NH), 1740 (C O ester),
1720 (C O ketone), 1525
(C N)
3295 (OH), 3125 (NH), 1760 (C
ester), 1710 (C O ketone),
1555 (C N)
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H, J =
7.2 Hz), 6.65 (s, 1H), 7.45–7.58 (m,
14H), 7.95 (s, 1H), 11.08 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.65 (s, 1H), 7.45–7.58
(m, 9H), 7.95 (s, 1H), 8 (s, 1H),
11.08 (s, 1H).
O
6b
6c
6d
3122 (NH), 1770 (C O ester),
1712 (C O ketone), 1525
(C N)
3120 (NH), 1755 (C O ester),
1720 (C O ketone), 1520
(C N)
3240 (NH), 1750 (C O ester),
1715 (C O ketone), 1526
(C N)
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.65 (s, 1H) 7.45–7.58
(m, 9H), 7.95 (s, 1H), 11.08 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H, J =
7.2 Hz), 6.63 (s, 1H) 7.42–7.55 (m,
910H), 7.93 (s, 1H), 11.05 (s, 1H).
1.2 (m, 6H), 1.4 (t, 3H, J = 7.2 Hz),
4.4 (q, 2H, J = 7.2 Hz), 6.60 (s, 1H),
7.40–50 (m, 9H), 7.90 (s, 1H),
11.00 (s, 1H).
6e
7a
3220 (NH), 1735 (C O ester),
1710 (C O keton) 1530
(C N)
3280 (OH), 3010 (NH),
1700 (C O ester), 1635
(C O ketone), 1560 (C N)
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.65 (s, 1H), 7.45–7.55
(m, 9H), 7.95 (s, 1H), 11.06 (s, 1H).
1.6 (t, 3H, J = 7.2 Hz), 4.6 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H), 7.50–8.01
(m, 9H), 7.96 (s, 1H), 11.08 (s, 1H),
11.50 (s, 1H).
7b
7c
3105 (NH), 1715 (C O ester),
1689 (C O ketone), 1540
(C N)
1.6 (t, 3H, J = 7.2 Hz), 4.6 (q, 2H,
J = 7.2 Hz), 7.50–8.01 (m, 9H),
6.70 (s, 1H) 7.96 (s, 1H), 11.08
(s, 1H) 11.50 (s, 1H).
1.4 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H) 7.2–7.7
(m, 10H), 7.6 (s, 1H), 11.05 (s, 1H)
11.40 (s, 1H).
3155 (NH), 1740 (C O ester),
1695 (C O ketone), 1555
(C N)

Synthesis and Studies
1009
TABLE II Selected IR, 1H NMR Spectra Data for the New Compounds
Listed in Table I (Continued)
Compound
1
no.
IR (cm
)
1H NMR (ppm)
7d
7e
8a
8b
8c
8d
8e
9a
9b
9c
10a
3205 (NH), 1760 (C O ester),
1699 (C O ketone),
1570 (C N)
1.3 (m, 6H), 1.6 (t, 3H, J = 7.2 Hz),
4.6 (q, 2H, J = 7.2 Hz), 6.70 (s, 1H)
7.6–8.20 (m, 9H), 8.4 (s, 1H), 11.06
(s, 1H) 11.45 (s, 1H).
1.6 (t, 3H, J = 7.2 Hz), 4.6 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H) 7.6–8.2
(m, 9H), 8.4 (s, 1H), 11.06 (s, 1H),
11.45 (s, 1H).
1.6 (t, 3H, J = 7.2 Hz), 4.6 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H) 7.6–8.2
(m, 9H), 8.4 (s, 1H), 11.06 (s, 1H),
11.45 (s, 1H), 12 (s, 1H).
1.6 (t, 3H, J = 7.2 Hz), 4.6 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H) 7.6–8.2
(m, 9H), 8.4 (s, 1H), 11.06 (s, 1H),
11.45 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 4.4 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H) 7.4–8.0
(m, 10H), 8.4 (s, 1H), 11.45 (s, 1H)
11.05 (s, 1H).
1.3 (m, 6H), 1.6 (t, 3H, J = 7.2 Hz),
4.6 (q, 2H, J = 7.2 Hz), 6.70 (s, 1H),
7.6–8.2 (m, 9H), 8.4 (s, 1H),11.06
(s, 1H), 11.45 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 4.6 (q, 2H,
J = 7.2 Hz), 6.70 (s, 1H), 7.6–8.2
(m, 9H), 8.4 (s, 1H), 11.06 (s, 1H),
11.45 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 3.5 (s, 1H),
4.4 (q, 2H, J = 7.2 Hz), 5.8 (s, 1H),
7.46–7.57 (m, 11H), 7.95 (s, 1H),
11.06 (s, 1H).
3189 (NH), 1750 (C O ester),
1705 (C O ketone),
1585 (C N)
3298 (OH), 3190 (NH),
1718 (C O ester), 1645 (C
ketone), 1592 (C N)
O
3199 (NH), 1765 (C O ester),
1690 (C O ketone), 1550
(C N)
3210 (NH), 1755 (C O ester),
1705 (C O ketone), 1560
(C N)
3195 (NH), 1750 (C O ester),
1710 (C O ketone), 1549
(C N)
3205 (NH), 1765 (C O ester),
1715 (C O keton) 1559
(C N)
3300 (OH), 3200 (NH),
1700 (C O ester), 1650
(C O amide), 1540 (C N)
3300 (OH), 3200 (NH),
1700 (C O ester), 1650
(C O amide), 1540 (C N)
1.3 (t, 3H, J = 7.2 Hz), 3.5 (s, 1H),
4.4 (q, 2H, J = 7.2 Hz), 5.8 (s, 1H),
7.46–7.57 (m, 11H), 7.95 (s, 1H),
11.06 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 1.5 (s, 3H),
3.5 (s, 1H) 4.4 (q, 2H, J = 7.2 Hz),
5.8 (s, 1H), 7.46–7.56 (m, 10H), 7.9
(s, 1H). 11.06 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 2 (s, 2H),
3.2 (b, 1H), 4.4 (q, 2H, J = 7.2 Hz),
5.8 (s, 1H), 7.46–7.56 (m, 11H),
7.9 (s, 1H), 11.06 (s, 1H).
3300 (OH), 3200 (NH),
1700 (C O ester), 1650
(C O amide), 1540 (C N)
3250 (OH), 3150 (NH),
1700 (C O ester), 1650
(C O amide), 1540 (C N)
(Continued on next page)

1010
H. A. Soleiman et al.
TABLE II Selected IR, 1H NMR Spectra Data for the New Compounds
Listed in Table I (Continued)
Compound
1
no.
IR (cm
)
1H NMR (ppm)
10b
10c
11a
11b
11c
3250 (OH), 3150 (NH),
1700 (C O ester), 1650
(C O amide), 1640 (C N)
1.3 (t, 3H, J = 7.2 Hz), 2 (s, 2H),
3.2 (br, 1H), 4.4 (q, 2H, J = 7.2 Hz),
5.8 (s, 1H), 7.46–7.56 (m, 11H), 7.9
(s, 1H), 11.06 (s, 1H).
1.5 (s, 3H), 1.3 (t, 3H, J = 7.2 Hz),
2 (s, 2H), 3.2 (br, 1H), 4.4 (q, 2H,
J = 7.2 Hz), 5.8 (s, 1H), 7.46–7.56
(m, 10H), 7.9 (s, 1H), 11.06 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 3.2 (br, 1H),
4.4 (q, 2H, J = 7.2 Hz), 5.8 (s, 1H),
7.46–7.56 (m, 11H), 7.9 (s, 1H),
11.06 (s, 1H).
1.3 (t, 3H, J = 7.2 Hz), 3.2 (br, 1H),
4.4 (q, 2H, J = 7.2 Hz), 5.8 (s, 1H),
7.46–7.56 (m, 11H), 7.9 (s, 1H),
11.06 (s, 1H).
1.5 (s, 3H), 1.3 (t, 3H, J = 7.2 Hz),
3.2 (br, 1H), 4.4 (q, 2H, J = 7.2 Hz),
5.8 (s, 1H), 7.46–7.56 (m, 10H),
7.9 (s, 1H), 11.06 (s, 1H),.
3250 (OH), 3150 (NH),
1700 (C O ester), 1650
(C O amide), 1640 (C N)
3250 (OH), 3150 (NH),
1700 (C O ester), 1650 (C
amide), 1640 (C N)
O
3250 (OH), 3150 (NH),
1700 (C O ester), 1650
(C O amide), 1640 (C N)
3250 (OH), 3150 (NH),
1700 (C O ester), 1650
(C O amide), 1640 (C N)
under the effect of concentrated hydrochloride acid as catalyst and one
mole of thiourea in ethanol as organic solvent under the effect of sodium
hydroxide as catalyst produced 7a–e and 8a–e respectively, (Scheme
1). The structure of (7a–e and 8a–e) were confirmed by Microanalyt-
ical data, Mass spectra, Infrared spectra and 1H NMR spectra (c.f.
Tables I and II). When chalcone compound derivatives (3a–f) were
condensed with nitroso compounds such as -nitroso- -naphthol,
-
nitroso- -naphthol, 3-methy1-4-oxime-1-pheny1-5-pyrazolone in the
presence piperidine as catalyst to give corresponding Schiff base deriva-
tives (9a–c), (Scheme 2). The structure of (9a–c) were confirmed by
Microanalytical data, Mass spectra, Infrared spectra and 1H NMR spec-
tra (c.f. Tables I and II). Cycloaddition reaction of thioglycolic acid to
previously prepared Schiff bases compound derivatives 9a–c proceeded
successfully. Thus, thioglycolic acid was added to 9a–c in boiling ben-
zene using a water separator to give thiazolidinone derivatives 10a–c
(Scheme 2). The structure of 10a–c were confirmed by Microanalytical
data, Mass spectra, Infrared spectra and 1H NMR spectra (c.f. Tables I
and II).
The reaction of chloroacetyl chloride in dioxane in the presence of tri-
ethylamine as catalyst afforded -lactam derivatives 11a–c (Scheme 2).

Synthesis and Studies
1011
SCHEME 2
The structures of (11a–c) were confirmed by Microanalytical data, Mass
spectra, Infrared spectra and 1H NMR spectra (c.f. Tables I and II).
EXPEREMENTAL
All melting points are uncorrected. The IR spectra were recorded on
a Perkin Elmer/1650 ET-IR spectrum, 1H NMR spectra on an EM-390
90MHz NMR spectrometer, mass spectra on an MS 5988 and Analytical
data were determined with a CE 440 Elemental Analyzer-Automatic
Injector at Cairo University.
Synthesis of Chalcone Compound Derivatives (3a–e)
General Procedure (1)
To a solution of 2 (0.001 mol, 0.5 g) and aromatic aldehydes
(0.001 mol, 0.17 g, 0.21 g, 0.14 ml, 0.20 g, and 0.19 g resp.) in
absolute alcohol, two drops of piperidine were added, the reaction
mixture was refluxed for 12–15 h, concentrated, cooled, filtered

1012
H. A. Soleiman et al.
and the chalcones, so obtained were purified and crystallized from
ethanol. Physical and chemical properties are summarized in Tables I
and II.
Synthesis of N-acetyl Pyrazolo Derivatives (4a–e)
General Procedure (2)
To a solution of chalcones 3a–e (0.002 mol, 0.922 g, 0.980 g, 0.890
g, 0.976 g, and 0.959 g resp.) in ethanol as a solvent, hydrazine hy-
drate (50%, 0.1 ml) was added in presence of few drops of acetic acid as
a catalyst. The reaction mixture was refluxed for 12–15 h, and then
the reaction mixture was concentrated, cooled. On trituration with
20 ml of petroleum ether a resins material was separated, decanted from
excess of petroleum ether. This material was triturated with water, then
the precipitate has separated, filtered, washed several times by water
and crystallized from ethanol. Physical and chemical properties were
summarized in Tables I and II.
Synthesis of N-phenyl Pyrazolo Derivatives (5a–e)
General Procedure (3)
To a solution of chalcones 3a–e (0.001 mol, 0.461 g, 0.490 g, 0.445 g,
0.488 g, and 0.480 g resp.) in ethanol as a solvent, phenyl hydrazine
(0.001 mol, 0.11 ml) was added in presence of few drops of piperdine as
a catalyst, the reaction mixture was refluxed for 15–20 h and then it
was concentrated to one-third of its volume and allowed to cool, then
the reaction mixture was poured to a mixture of ice/HCl, a brown pre-
cipitate was separated, filtered, washed for several times of water, dried
and crystallized from ethanol. Physical and chemical properties of 5a–e
were summarized in Tables I and II.
Synthesis of Isoxazolo Derivatives (6a–e)
General Procedure (4)
(0.001 mol, 0.461 g, 0.490 g, 0.445 g, 0.488 g, and 0.480 g resp.)
of chalcones 3a–c and (0.001 mol, 0.069 g) of hydroxylamine hy-
drochloride were refluxed in presence of sodium hydroxide as a
catalyst and ethanol as a solvent for 15–20 h, the reaction mixture was
filtered off from unreacted material, the filtrate was concentra-
ted, added to ice-HCl mixture, the precipitate was separated,
filtered, washed by water, dried and crystallized from ethanol, phys-
ical and chemical properties of 6a–e were summarized in Tables I
and II.

Synthesis and Studies
1013
Synthesis of Pyrimidino Derivatives (7a–e)
General Procedure (5)
An alcoholic solution of chalcones 3a–e (0.002 mol, 0.922 g, 0.980 g,
0.890 g, 0.976 g, and 0.959 g resp.) was refluxed with urea (0.002 mol,
0.12 g) and 2 ml of HCl concentrated on water bath for 12–15 h.
The reaction mixture was filtered on hot, allowed to cool, neutralized
with 5N NaOH, then a precipitate was separated, filtered, washed by
water for several times, dried and crystallized from ethanol. Physical
and chemical properties of 7a–e were summarized in Tables I and II.
Synthesis of Thio Pyrimido Derivatives (8a–e)
General Procedure (6)
Chalcones 3a–e (0.002 mol, 0.922 g, 0.980 g, 0.890 g, 0.976 g, and
0.959 g resp.) were refluxed with thiourea (0.002 mol, 0.152 g) in pres-
ence of sodium hydroxide as a catalyst, and ethanol as a solvent for
15–20 h, the reaction mixture was concentrated poured on ice-HCl
mixture, the precipitate was separated, filtered, washed by water for
several times, dried and crystallized from ethanol, physical and chem-
ical properties of 8a–e were summarized in Tables I and II.
Synthesis of Schiff Base Compound Derivatives (9a–c)
General Procedure (7)
To a solution of 2 (0.001 mol, 0.5 g) and nitroso compounds such
as -nitroso- -naph-thol, -nitroso- -naphthol and 3-methyl-1-phenyl-
4-oxime-5-pyrazolone (0.001 mol, 0.173 g, 0.173, and 0.203 g) respec-
tively in absolute ethanol, two drops of piperidine were added. The
reaction mixture was refluxed for 8–10 h, filtered on hot, concentrated
and cooled, the Schiff base so obtained were purified and crystallized
from ethanol. Physical and chemical properties of 9a–c were summa-
rized in Tables I and II.
Synthesis of Thiazolidino Derivatives (10a–c)
General Procedure (8)
An equimolar mixture of 9a–c (0.001 mol, 0.512 g, 0.512 g, and 0.452 g
resp.) and mercaptoacetic acid (0.001 mol, 0.092 g) in dry benzene
(50 ml) were refluxed for 15 h. The reaction mixture was then evapo-
rated to one-third under reduced pressure and allowed to stand at room
temperature. In most cases the thiazolidinone was separated with addi-
tion of ice-water on the triturated residue, and the product was washed

1014
H. A. Soleiman et al.
with water, and crystallized from ethanol physical and chemical prop-
erties of 10a–c were summarized in Tables I and II.
Synthesis of -lactam Derivatives (11a–c)
General Procedure (9)
To a well stirred solution of 9a–c (0.001 mol, 0.512 g, 0.512 g, and
542 g resp.) and triethylamine (0.002 mol, 0.202 g) in dry dioxane
(50 ml) was added chloroacetyl chloride (0.002 mol, 0.226 g) dropwise at
room temperature. The mixture was stirred for an additional 9 h, and
left at room temperature for 3 dyes. The precipitate of triethylamine
hydrochloride was filtered off and washed throughly with dioxane. The
filterate was evaporated to one-third of its original volume, cooled and
ice-water was added. The residue was washed with water and crys-
tallized from ethanol, physical and chemical properties of 11a–c were
summarized in Tables I and II.
REFERENCES
[1] A. K. Khalafallah, A. I. M. Koraiem, M. E. Hassan, and H. A. Soleiman, Indian
Chem. Soc., 69, 318 (1992).
[2] A. K. Khalafallah, M. A. Selim, R. M. Abu-Elhamd, M. A. El-Maghraby, H. A.
Soleiman, and M. A. Raslan, Indian J. Chem., 34B, 1066–1070 (1995).
[3] M. A. El-Maghraby, A. K. Khalafallah, M. E. Hassan, and H. A. Soleiman, J. Chin.
Chem. Soc., 35, 278 (1988).
[4] M. A. El-Maghraby, A. K. Khalafallah, M. E. Hassan, and H. A. Soleiman, J. Chin.
Chem. Soc., LX III, 910 (1986).
[5] H. A Soleiman, A. K. Khalafallah, and H. M. Abdelzaher, J. Chin. Chem. Soc., 47,
1267–1272 (2000).
[6] E. C. Taylor, J. Heterocycl. Chem., 27, 1 (1990).
[7] Y. Tominaga, S. Kohra, H. Honkawa, and A. Hosomi, J. Heterocycles, 29, 1409 (1989).
[8] Y. Tominaga, S. Motokawa, Y. Shiroshita, and A. Hosomi, J. Heterocycl. Chem., 24,
1365 (1987).
[9] R. K. Robins, P. C. Stivastava, and G. R. Revankar, Lectures in Heterocyclic Chem-
istry VI: Novel Nitrogen Heterocycles as Potential Medicinal Agents, (Heterocorpo-
ration, Tampa, FL 1982), p. 93.
[10] Y. Tominaga, S. Kohra, H. Okuda, A. Ushirogouchi, Y. Matsuda, and G. Kobayshi,
Chem. Pharm, Bull., 32, 122 (1984).
[11] Z. Yam, Sligehoru, Japan Koka; 75, 158, 542 (1975), Appl. 74, 65, 991 (1994).
[12] M. H. Elnagdi, A. M. Negm, and A.W. Erian, Liebigs Ann. Chem., 1255 (1989);
M. H. Elnagdi, A. M. Negm, E. M. Hassan, A. El-Boreiy, J. Chem. Res(s)., 130
(1993).
[13] M. H. Elnagdi, A. W. Erian, K. U. Sadek, and M. A. Selim, J. Chem. Res(s)., 148, (m)
1990, 1124 (1990).
[14] M. H. Elnagdi and A. W. Erian, Liebigs Ann. Chem., 1215.