Efficient, simple synthesis of stable phosphorus ylides derived from 4-aryl urazoles

Article abstract of DOI:10.1080/10426500903251357

Crystalline phosphorus ylides are obtained in nearly quantitative yields from the 1:1:1 addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylates, and 4-aryl urazoles. Copyright Taylor & Francis Group, LLC.

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Phosphorus, Sulfur, and Silicon and the
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Efficient, Simple Synthesis of Stable
Phosphorus Ylides Derived from 4-Aryl
Urazoles
Mehdi Adib a , Moharram Omidi a & Hamid Reza Bijanzadeh b
a School of Chemistry, University College of Science , University of
Tehran , Tehran, Iran
b Department of Chemistry , Tarbiat Modarres University , Tehran,
Iran
Published online: 02 Aug 2010.
To cite this article: Mehdi Adib , Moharram Omidi & Hamid Reza Bijanzadeh (2010) Efficient, Simple
Synthesis of Stable Phosphorus Ylides Derived from 4-Aryl Urazoles, Phosphorus, Sulfur, and Silicon
and the Related Elements, 185:8, 1732-1738, DOI: 10.1080/10426500903251357
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Phosphorus, Sulfur, and Silicon, 185:1732–1738, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500903251357
EFFICIENT, SIMPLE SYNTHESIS OF STABLE
PHOSPHORUS YLIDES DERIVED FROM
4-ARYL URAZOLES
Mehdi Adib,1 Moharram Omidi,1 and Hamid Reza Bijanzadeh2
1School of Chemistry, University College of Science, University of Tehran,
Tehran, Iran
2Department of Chemistry, Tarbiat Modarres University, Tehran, Iran
Crystalline phosphorus ylides are obtained in nearly quantitative yields from the 1:1:1
addition reaction between triphenylphosphine, dialkyl acetylenedicarboxylates, and 4-aryl
urazoles.
Keywords Acetylenic esters; 4-aryl urazoles; phosphoranes; triphenylphosphine
INTRODUCTION
Among a large variety of nitrogen-containing heterocyclic compounds, those con-
taining a urazole moiety are of interest because they constitute an important class of natural
and non-natural products, many of which exhibit useful biological activities.1 Some urazole
derivatives have been shown to possess anticonvulsant,2 fungicidal,3 antineoplastic,4 hy-
polipidemic,5 antiinflammatory,6 and antidepressant7 activities as well as catalytic activity
in radical polymerization.8
Phosphorus ylides are reactive intermediates that take part in many valuable reac-
tions in organic synthesis.9–22 Several methods have been developed for the preparation
of phosphorus ylides. These ylides are usually prepared by treatment of a phosphonium
salt with a base, and phosphonium salts are usually prepared from the phosphine and an
alkyl halide.9–11 Phosphonium salts are also prepared by Michael addition of phosphorus
nucleophiles to activated olefins among other methods.9
Recently, there are many reports in literature on the synthesis of phosphorus ylides by
three-component reaction of electron-deficient acetylenic compounds and triphenylphos-
phine in the presence of various organic N-H, O-H, C-H, and S-H acids.23
Received 9 June 2009; accepted 11 August 2009.
This research was supported by the Research Council of the University of Tehran as a research project
(6102036/1/03).
Address correspondence to Mehdi Adib, School of Chemistry, University College of Science, University of
Tehran, PO Box 14155-6455, Tehran, Iran. E-mail: madib@khayam.ut.ac.ir
1732

SYNTHESIS OF STABLE PHOSPHORUS YLIDES
1733
RESULTS AND DISCUSSION
As part of our current studies on the development of efficient and facile methods for
the preparation of organic compounds,24 we report in this article an efficient synthetic route
to phosphorus ylides derived from 4-aryl urazoles. Thus, a mixture of triphenylphosphine,
a dialkyl acetylenedicarboxylate 1, and a 4-aryl urazole 2 underwent a one-pot, three-
component reaction to afford the corresponding phosphorus ylides 3 in nearly quantitative
yields (Scheme 1).
Ar
O
N
O
NH
O
N
acetone
r.t., 2 h
HN
HN
(C6H5)3P
+
+
RO2C
C
C
CO2R
N Ar
CO2R
P(C6H5)3
RO2C
O
2
3
1
R
Ar
R
Ar
C6H5
% Yield
1
2
3
a
CH3
C6H5
a
a
b
c
CH3
99
98
99
96
98
94
C2H5
3,4-Cl2C6H3
3-Cl-4-CH3C6H3
b
CH2CH3 C6H5
b
c
d
e
f
CH3
CH2CH3 3,4-Cl2C6H3
CH3 3-Cl-4-CH3C6H3
CH2CH3 3-Cl-4-CH3C6H3
3,4-Cl2C6H3
Scheme 1
The reaction of triphenylphosphine with dialkyl acetylenedicarboxylates in the pres-
ence of 4-aryl urazoles proceeded spontaneously at room temperature in acetone, and was
1
complete within 2 h. H and 13C NMR spectra of the crude product clearly indicated the
formation of the phosphoranes 3. Any product other than 3 could not be detected by NMR
spectroscopy.
1
The structures of the isolated products 3a–f were deduced on the basis of IR, H,
13C, and 31P NMR spectroscopy, mass spectrometry, and elemental analysis. The nature of
these compounds as 1:1:1 adducts was apparent from their mass spectra, which displayed
molecular ion [M+] peaks at m/z = 581, 609, 650, 678, 630, and 658, respectively. Initial
fragmentations involve loss from or complete loss of the side chains and scission of the
heterocyclic ring system.
We have reported25,26 the synthesis of several functionalized phosphoranes via one-
pot, three-component reactions between triphenylphosphine, dialkyl acetylenedicarboxy-
lates, and some NH-acids. Dynamic NMR effects were observed in the 1H NMR spectra of
the reported ylides and were attributed to restricted rotation around the carbon–carbon par-
tial double bond resulting from conjugation of the ylide moiety with the adjacent carbonyl

1734
M. ADIB ET AL.
group. However, the 1H, 13C NMR spectra of the ylides synthesized from 4-aryl urazoles
3a–f are consistent with the presence of only one isomer, and the minor isomer is present in
less than 3% (on the basis of 31P NMR). In the Z geometrical isomer of these ylides, there
is strong hydrogen bonding between O− of the ylide moiety and the adjacent NH group,
which could stabilize the Z isomer.
Ar
N
Ar
N
O
O
O
O
N
N
N
N
H
H
H
H
_
RO2C
RO2C
OR
O
_
O
+
+
OR
(C6H5)3P
(C6H5)3P
3-(E), trace
3-(Z)
On the basis of the well established chemistry of trivalent phosphorus nucle-
ophiles,9–22 it is reasonable to assume that phosphorus ylide 3 results from the initial
addition of triphenylphosphine to the acetylenic ester and subsequent protonation of the
zwitterionic intermediate 4 by the NH-acid 2. Then the positively charged ion 5 is attacked
by the conjugate base of the NH-acid 6 to form phosphorane 3 (Scheme 2).
_
2
RO2C
CO R
C
(C6H5)3P
+
RO2C
C
C
CO2R
2
+
(C6H5)3P
1
4
Ar
N
O
Ar
N
NH
O
RO2C
O
O
N
CH
CO2R
+
CO2R
N
_
N
(C6H5)3P
RO2C
H
P(C6H5)3
5
6
3
Scheme 2
Functionalized phosphorus ylides 3a–f may be considered as potentially useful syn-
thetic intermediates.9,10 Excellent yields of the products and relatively short reaction times
are the main advantages of this method. The reactions were performed under neutral and
mild conditions, and the starting materials and reagents can be mixed without any acti-
vation or modification. The procedure described here may be an acceptable method for
the preparation of phosphoranes with variable functionalities. The one-pot nature of the
present procedure makes it an interesting alternative to multistep approaches.9–18 In view of
widespread biological activities of urazole derivatives, the urazole-containing phosphorus

SYNTHESIS OF STABLE PHOSPHORUS YLIDES
1735
ylides prepared in the present study may find useful applications in synthetic organic and
bioorganic chemistry.
EXPERIMENTAL
Dialkyl acetylenedicarboxylates and triphenylphosphine were obtained from Merck
(Germany) and were used without further purification. 4-Aryl urazoles were prepared
according to the procedure in the literature.27 Melting points were measured on an Elec-
trothermal 9100 apparatus. Elemental analyses for C, H, and N were performed using a
Heraeus CHN-O-Rapid analyzer. Mass spectra were recorded on a Finnigan-MATT 8430
1
mass spectrometer operating at an ionization potential of 20 eV. H, 13C, and 31P NMR
spectra were measured (CDCl3 solution) with a Bruker DRX-500 AVANCE spectrometer
at 500.1, 125.8, and 202.5 MHz, respectively. IR spectra were recorded on a Shimadzu
IR-460 spectrometer.
Preparation of Dimethyl 2-(4-Phenyl-3,5-dioxo-1,2,4-triazolin-1-yl)-3-
(triphenylphosphoranylidene)butanedioate (3a)
To a magnetically stirred solution of triphenylphosphine (0.262 g, 1 mmol) and 4-
phenyl urazole 2a (0.177 g, 1 mmol) in acetone (6 mL), a solution of dimethyl acetylenedi-
carboxylate 1a (0.148 g, 1 mmol) in acetone (2 mL) at −5◦C was added dropwise over 10
min. The reaction mixture was then allowed to warm to room temperature and stirred for
2 h. The white precipitate was filtered and washed with cold acetone. The product 3a was
recrystallized from EtOAc/n-hexane (2:1) as colorless crystals, mp 149–151◦C, yield 0.58
g, 99%. IR (KBr) (νmax/cm−1): 3210 (NH), 1760 (shoulder), 1732 (shoulder), 1691 (C O),
1647, 1610, 1489, 1423, 1301, 1230, 1130, 1100, 761, 712, 689, 536. MS, m/z (%): 581
(M+, 25), 566 (20), 447 (10), 419 (75), 262 (100), 183 (46), 177 (45), 144 (29), 94 (20), 77
(10). Anal. Calcd. for C32H28N3O6P (581.56): C, 66.09; H, 4.85; N, 7.23. Found: C, 66.4;
H, 4.8; N, 7.0%. 1H NMR: δ 3.15 and 3.75 (6 H, 2 s, 2 OCH3), 4.74 (1 H, d, 3JPH 16.6 Hz,
P-C-CH), 7.34 (1 H, t, J 7.1 Hz, CH), 7.42 (2 H, t, J 8.0 Hz, 2 CH), 7.51 (2 H, d, J 7.8
Hz, 2 CH), 7.57–7.75 (9 H, m, 6 CHmeta and 3 CHpara), 7.81 (6 H, dd, J 8.1 Hz and J 12.3
Hz, 6 CHortho), 9.93 (1 H, br. s, NH). 13C NMR: δ 40.16 (d, 1JPC 128.2 Hz, P C), 48.08
and 51.26 (2 OCH3), 57.39 (d, 2JPC 16.8 Hz, P-C-CH), 124.53 (CH), 124.95 (d, 1JPC 92.4
3
4
Hz, Cipso), 126.21 and 127.53 (2 CH), 128.15 (d, JPC 12.4 Hz, CHmeta), 131.66 (d, JPC
2.9 Hz, CHpara), 131.78 (C), 132.62 (d, 2JPC 9.9 Hz, CHortho), 150.77 and 151.03 (2 C O,
urea), 169.73 and 170.65 (2 d, 2JPC 10.9 Hz and 3JPC 12.5 Hz, 2 C O ester). 31P NMR: δ
23.81 (Ph3P+-C).
Diethyl 2-(4-Phenyl-3,5-dioxo-1,2,4-triazolin-1-yl)-3-(triphenylphosphor
anylidene)butanedioate (3b)
Colorless crystals, mp 132–134◦C, yield 0.59 g, 98%. IR (KBr) (νmax/cm−1): 3195
(NH), 1761, 1732, 1696 (C O), 1631, 1595, 1489, 1423, 1367, 1298, 1227, 1130, 1101,
1022, 771, 748, 710, 688, 548, 511. MS, m/z (%): 609 (M+, 17), 490 (25), 462 (31), 262
(89), 183 (100), 177 (10), 77 (28). Anal. Calcd. for C34H32N3O6P (609.62): C, 66.99; H,
5.29; N, 6.89. Found: C, 66.6; H, 5.2; N, 6.7%. 1H NMR: δ 0.50 and 1.29 (6 H, 2 t, J 7.1
3
Hz, 2 OCH2CH3), 3.75 and 4.23 (4 H, 2 m, 2 OCH2CH3), 4.80 (1 H, d, JPH 16.5 Hz,
P-C-CH), 7.28 (1 H, t, J 7.4 Hz, CH), 7.39 (2 H, t, J 7.7 Hz, 2 CH), 7.48 (2 H, d, J 7.9 Hz,

1736
M. ADIB ET AL.
2 CH), 7.53 (6 H, dt, J 2.5 Hz and J 7.5 Hz, 6 CHmeta), 7.62 (3 H, t, J 7.1 Hz, 3 CHpara),
7.72 (6 H, dd, J 7.7 Hz and J 12.5 Hz, 6 CHortho), 10.03 (1 H, s, NH). 13C NMR: δ 13.86
and 14.21 (2 OCH2CH3), 42.39 (d, 1JPC 128.4 Hz, P C), 57.89 (d, 2JPC 16.5 Hz, P-C-CH),
58.74 and 61.99 (2 OCH2CH3), 125.62 (d, 1JPC 92.7 Hz, Cipso), 125.71, 127.53, and 128.90
(3 CH), 129.06 (d, 3JPC 12.7 Hz, CHmeta), 132.14 (C), 132.65 (CHpara), 133.65 (d, 2JPC 9.9
Hz, CHortho), 151.28 and 151.42 (2 C O, urea), 170.37 and 172.11 (2 d, 2JPC 10.2 Hz and
3JPC 12.3 Hz, 2 C O ester). 31P NMR: δ 23.00 (Ph3P+-C).
Dimethyl 2-[4-(3,4-Dichlorophenyl)-3,5-dioxo-1,2,4-triazolin-1-yl]-3-
(triphenylphosphoranylidene)butanedioate (3c)
Colorless crystals, mp 145–147◦C, yield 0.64 g, 99%. IR (KBr) (νmax/cm−1): 3150
(NH), 1762, 1736, 1697 (C O), 1607, 1468, 1421, 1320, 1294, 1225, 1144, 1100, 747,
711, 688, 512. MS, m/z (%): 650 (M+, 8), 635 (7), 404 (14), 376 (61), 262 (97), 183 (100),
174 (24), 161 (16), 78 (25). Anal. Calcd. for C32H26Cl2N3O6P (650.45): C, 59.09; H, 4.03;
N, 6.46. Found: C, 59.3; H, 3.8; N, 6.4%. 1H NMR: δ 3.20 and 3.78 (6 H, 2 s, 2 OCH3),
4.79 (1 H, d, 3JPH 16.2 Hz, P-C-CH), 7.46 (2 H, br., 2 CH), 7.55 (6 H, dt, J 2.3 Hz and J
7.4 Hz, 6 CHmeta), 7.64 (3 H, t, J 7.1 Hz, 3 CHpara), 7.70 (6 H, dd, J 7.8 Hz and J 12.5
Hz, 6 CHortho), 7.72 (1 H, br., CH), 10.08 (1 H, s, NH). 13C NMR: δ 42.59 (d, 1JPC 128.3
2
Hz, P C), 50.10 and 53.20 (2 OCH3), 57.78 (d, JPC 17.0 Hz, P-C-CH), 124.43 (CH),
1
3
125.35 (d, JPC 92.6 Hz, Cipso), 127.04 (CH), 129.19 (d, JPC 11.7 Hz, CHmeta), 130.41
(CH), 131.28, 131.71, and 132.67 (3 C), 132.79 (CHpara), 133.57 (d, 2JPC 9.8 Hz, CHortho),
150.09 and 150.43 (2 C O, urea), 170.78 and 172.58 (2 d, 2JPC 10.3 Hz and 3JPC 12.3 Hz,
2 C O ester). 31P NMR: δ 23.38 (Ph3P+-C).
Diethyl 2-[4-(3,4-Dichlorophenyl)-3,5-dioxo-1,2,4-triazolin-1-yl]-3-
(triphenylphosphoranylidene)butanedioate (3d)
Colorless crystals, mp 127–129◦C, yield 0.65 g, 96%. IR (KBr) (νmax/cm−1): 3190
(NH), 1761, 1732 (shoulder), 1700 (C O), 1628, 1594, 1469, 1426, 1368, 1305, 1232,
1129, 1100, 1021, 711, 689, 549, 511. MS, m/z (%): 678 (M+, 5), 649 (11), 432 (15),
404 (43), 245 (15), 262 (100), 183 (84), 174 (14), 161 (18), 77 (31). Anal. Calcd. for
C34H30Cl2N3O6P (678.51): C, 60.19; H, 4.46; N, 6.19. Found: C, 59.9; H, 4.5; N, 6.4%.
1H NMR: δ 0.48 and 1.26 (6 H, 2 t, J 7.1 Hz, 2 OCH2CH3), 3.72 and 4.20 (4 H, 2 m, 2
OCH2CH3), 4.73 (1 H, d, 3JPH 16.5 Hz, P-C-CH), 7.43 (2 H, br., 2 CH), 7.51 (6 H, dt, J
2.4 Hz and J 7.4 Hz, 6 CHmeta), 7.61 (3 H, t, J 7.0 Hz, 3 CHpara), 7.68 (6 H, dd, J 7.9 Hz
and J 12.6 Hz, 6 CHortho), 7.69 (1 H, br., CH), 10.19 (1 H, s, NH).13C NMR: δ 13.80 and
1
2
14.15 (2 OCH2CH3), 41.43 (d, JPC 128.4 Hz, P C), 57.94 (d, JPC 16.9 Hz, P-C-CH),
58.84 and 62.08 (2 OCH2CH3), 124.40 (CH), 125.48 (d, 1JPC 92.6 Hz, Cipso), 126.99 (CH),
129.05 (d, 3JPC 11.7 Hz, CHmeta), 130.34 (CH), 131.21, 131.70, and 132.62 (3 C), 132.68
(CHpara), 133.57 (d, 2JPC 10.1 Hz, CHortho), 150.46 and 150.51 (2 C O, urea), 170.08 and
172.20 (2 d, 2JPC 10.3 Hz and 3JPC 12.4 Hz, 2 C O ester). 31P NMR: δ 23.02 (Ph3P+-C).
Dimethyl 2-[4-(3-Chloro-4-methylphenyl)-3,5-dioxo-1,2,4-triazolin-1-yl]-
3-(triphenylphosphoranylidene)butanedioate (3e)
Colorless crystals, mp 162–164◦C, yield 0.62 g, 98%. IR (KBr) (νmax/cm−1): 3140
(NH), 1760, 1738, 1694 (C O), 1609, 1489, 1421, 1322, 1293, 1224, 1145, 1100, 711,

SYNTHESIS OF STABLE PHOSPHORUS YLIDES
1737
689, 527. MS, m/z (%): 630 (M+, 21), 404 (16), 376 (29), 262 (100), 225 (54), 183 (79),
144 (19), 78 (10). Anal. Calcd. for C33H29ClN3O6P (630.04): C, 62.91; H, 4.64; N, 6.67.
Found: C, 62.6; H, 4.3; N, 6.6%. 1H NMR: δ 2.33 (3 H, s, CH3), 3.17 and 3.76 (6 H, 2 s, 2
OCH3), 4.76 (1 H, d, 3JPH 16.2 Hz, P-C-CH), 7.23 (1 H, d, J 8.2 Hz, CH), 7.28 (1 H, dd,
J 8.2 Hz and J 1.2 Hz, CH), 7.48 (1 H, d, J 1.2 Hz, CH), 7.52 (6 H, dt, J 1.7 Hz and J 7.3
Hz, 6 CHmeta), 7.61 (3 H, t, J 7.4 Hz, 3 CHpara), 7.67 (6 H, dd, J 7.6 Hz and J 12.4 Hz,
6 CHortho), 9.84 (1 H, s, NH). 13C NMR: δ 19.67 (CH3), 42.55 (d, 1JPC 128.4 Hz, P C),
49.96 and 53.09 (2 OCH3), 57.63 (d, 2JPC 17.0 Hz, P-C-CH), 123.84 (CH), 125.42 (d, 1JPC
92.4 Hz, Cipso), 126.17 (CH), 129.10 (d, 3JPC 12.5 Hz, CHmeta), 130.63 (C), 130.90 (CH),
2
132.67 (CHpara), 133.54 (d, JPC 9.9 Hz, CHortho), 134.32 and 135.57 (2 C), 150.46 and
2
3
150.91 (2 C O, urea), 170.89 and 172.41 (2 d, JPC 10.3 Hz and JPC 12.6 Hz, 2 C O
ester). 31P NMR: δ 22.96 (Ph3P+-C).
Diethyl 2-[4-(3-Chloro-4-methylphenyl)-3,5-dioxo-1,2,4-triazolin-1-yl]-3-
(triphenylphosphoranylidene)butanedioate (3f)
Colorless crystals, mp 125–127◦C, yield 0.62 g, 94%. IR (KBr) (υmax/cm−1): 3210
(NH), 1759, 1729, 1697 (C O), 1632, 1489, 1423, 1366, 1299, 1228, 1134, 1101, 690.
MS, m/z (%): 658 (M+, 11), 629 (8), 432 (20), 404 (52), 262 (100), 183 (84), 174 (12),
141 (36), 78 (15). Anal. Calcd. for C35H33ClN3O6P (658.09): C, 63.88; H, 5.05; N, 6.39.
Found: C, 63.4; H, 4.9; N, 6.5%. 1H NMR: δ 0.41 and 1.21 (6 H, 2 t, J 7.0 Hz, 2 OCH2CH3),
3
2.23 (3 H, s, CH3), 3.67 and 4.18 (4 H, 2 m, 2 OCH2CH3), 4.73 (1 H, d, JPH 16.5 Hz,
P-C-CH), 7.15 (1 H, d, J 8.2 Hz, CH), 7.25 (1 H, dd, J 8.2 Hz and J 1.2 Hz, CH), 7.40–7.48
(7 H, m, CH and 6 CHmeta), 7.53 (3 H, t, J 7.3 Hz, 3 CHpara), 7.66 (6 H, dd, J 7.6 Hz and
J 12.4 Hz, 6 CHortho), 10.15 (1 H, s, NH).13C NMR: δ 13.77 and 14.19 (2 OCH2CH3),
19.60 (CH3), 41.89 (d, 1JPC 127.8 Hz, P C), 58.12 (d, 2JPC 17.0 Hz, P-C-CH), 58.72 and
61.94 (2 OCH2CH3), 123.80 (CH), 125.50 (d, 1JPC 92.1 Hz, Cipso), 126.05 (CH), 129.00 (d,
3JPC 12.6 Hz, CHmeta), 130.77 (C), 130.84 (CH), 132.64 (CHpara), 133.60 (d, 2JPC 9.8 Hz,
CHortho), 134.16 and 135.36 (2 C), 150.10 and 151.18 (2 C O, urea), 170.24 and 171.95
(2 d, 2JPC 10.2 Hz and 3JPC 12.4 Hz, 2 C O ester). 31P NMR: δ 23.08 (Ph3P+-C).
REFERENCES
1. (a) X. Lei, N. Zaarur, M. Y. Sherman, and J. A. Porco Jr., J. Org. Chem., 70, 6474 (2005); (b) A.
Kiriazis, T. Ruffer, S. Jantti, H. Lang, and J. Yli-Kauhaluama, J. Comb. Chem., 9, 263 (2007);
(c) P. D. Boatman, J. Urban, M. Nguyen, M. Qabar, and M. Kahn, Bioorg. Med. Chem. Lett.,
13, 1445 (2003); (d) V. M. Kolb, J. P. Dworkin, and S. L. Miller, J. Mol. Evol., 38, 549 (1994);
(e) R. A. Izydore, J. A. Bernal-Ramirez, and P. Singh, J. Org. Chem., 55, 3761 (1990).
2. C. R. Jacobson, A. D’Adamo, and C. E. Cosgrove, US Patent 3,663,564 (1972).
3. T. Shgematsu, M. Tomita, T. Shibahara, M. Nakazawa, and S. Munakata, Jpn. Patent 52,083,562
(1977).
4. I. H. Hall, O. T. Wong, R. Simlot, M. C. Miller, and R. A. Izydore, Anticancer Res., 12, 1355
(1992).
5. R. Simlot, R. A. Izydore, O. T. Wong, and I. H. Hall, J. Pharm. Sci., 83, 367 (1994).
6. I. H. Hall, R. Simlot, and R. A. Izydore, Arch. Pharm., 328, 5 (1995).
7. R. F. Mayol and G. M. Luke, EP Patent 568,437 (1993).
8. E. Baumgartner, U. Blumenstein, R. Bueschl, and N. Reieber, EP Patent 390,026 (1990).
9. D. E. C. Corbridge, Phosphorus: An Outline of the Chemistry, Biochemistry and Uses, 5th ed.
(Elsevier, Amsterdam, 1995).

1738
M. ADIB ET AL.
10. R. Engel, Synthesis of Carbon–Phosphorus Bonds (CRC Press, Boca Raton, FL, 1988).
11. J. I. G. Cadogan, Organophosphorus Reagents in Organic Synthesis (Academic Press, New York,
1979).
12. A. W. Johnson, Ylides and Imines of Phosphorus (Wiley, New York, 1993).
13. A. W. Johnson, Ylide Chemistry (Academic Press, New York, 1966).
14. O. I. Kolodiazhynyi, Russ. Chem. Rev., 66, 225 (1997).
15. H. J. Bestmann and R. Zimmermann, Top. Curr. Chem., 20, 88 (1971).
16. H. J. Bestmann and O. Vostrowsky, Top. Curr. Chem., 109, 85 (1983).
17. B. E. Maryano and A. B. Reitz, Chem. Rev., 89, 863 (1989).
18. K. M. Pietrusiewiz and M. Zablocka, Chem. Rev., 94, 109 (1994).
19. R. A. Aitken, H. Herion, A. Janosi, N. Karodia, S. V. Raut, S. Seth, I. J. Shanon, and F. C. Smith,
J. Chem. Soc., Perkin Trans. 1, 2467 (1994).
20. E. Zbiral, Synthesis, 775 (1974).
21. P. Ferrer, C. Avendo, and M. Sollhubor, Liebigs Ann. Chem., 1895 (1995).
22. K. B. Becker, Tetrahedron, 36, 1717 (1980).
23. (a) M. Anary-Abbasinejad, H. Anaraki-Ardakani, and H. Hosseini-Mehdiabad, Phosphorus,
Sulfur, and Silicon, 183, 1440 (2008); (b) R. Heydari, M. T. Maghsoodlou, and R. N. Yami,
Phosphorus, Sulfur, and Silicon, 183, 2578 (2008); (c) A. R. Kazemizadeh, A. Ramazani, and
B. Ganjeie, Phosphorus, Sulfur, and Silicon, 183, 1935 (2008); (d) A. Jafari, E. Ahmadi, and A.
Ramazani, Phosphorus, Sulfur, and Silicon, 183, 1489 (2008); (e) I. Amini, A. Ramazani, and
H. Ahankar, Phosphorus, Sulfur, and Silicon, 183, 1994 (2008); (f) M. Adib, E. Sheibani, M.
Mostofi, K. Ghanbary, and H. R. Bijanzadeh, Phosphorus, Sulfur, and Silicon, 180, 2701 (2005).
24. (a) M. Adib, E. Sheibani, H. R. Bijanzadeh, and L. G. Zhu, Tetrahedron, 64, 10681 (2008);
(b) M. Adib, M. H. Sayahi, H. Ziyadi, L. G. Zhu, and H. R. Bijanzadeh, Synthesis, 3289 (2008);
(c) M. Adib, E. Sheibani, L. G. Zhu, and H. R. Bijanzadeh, Synlett, 2941 (2008); (d) M. Adib,
B. Mohammadi, and H. R. Bijanzadeh, Synlett, 3180 (2008); (e) M. Adib, B. Mohammadi, and
H. R. Bijanzadeh, Synlett, 177 (2008); (f) M. Adib, M. H. Sayahi, H. Ziyadi, H. R. Bijanzadeh,
and L. G. Zhu, Tetrahedron, 63, 11135 (2007); (g) M. Adib, S. Aali Koloogani, A. Abbasi,
and H. R. Bijanzadeh, Synthesis, 3056 (2007); (h) M. Adib, E. Sheibani, A. Abbasi, and H.
R. Bijanzadeh, Tetrahedron Lett., 48, 1179 (2007); (i) M. Adib, E. Sheibani, M. Mostofi, K.
Ghanbary, and H. R. Bijanzadeh, Tetrahedron, 62, 3435 (2006); (j) M. Adib, M. Mahdavi, N.
Mahmoodi, H. Pirelahi, and H. R. Bijanzadeh, Synlett, 1765 (2006).
25. I. Yavari, M. Adib, F. Jahani-Mogaddam, and M. H. Sayahi, Phosphorus, Sulfur, and Silicon,
177, 545 (2001).
26. I. Yavari and M. Adib, Tetrahedron, 57, 5873 (2001).
27. E. H. Huntress, T. E. Lesslie, and J. Bornstein, Org. Synth. Coll. Vol. IV, 329 (1963).