Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles

Article abstract of DOI:10.1007/s00706-011-0489-3

The 1:1 intermediate generated by the addition of triphenylphosphine to dialkyl acetylenedicarboxylates is trapped by alizarin to produce alkyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-carboxylates in good yields. When ethyl propi

Full text of DOI:10.1007/s00706-011-0489-3

Monatsh Chem (2011) 142:643–647
DOI 10.1007/s00706-011-0489-3
ORIGINAL PAPER
Synthesis of new functionalized alizarins from alizarin, acetylenic
esters, and phosphorus nucleophiles
•
Issa Yavari Leila Azad Tayebeh Sanaeishoar
•
Received: 6 December 2010 / Accepted: 20 March 2011 / Published online: 20 April 2011
Ó Springer-Verlag 2011
Abstract The 1:1 intermediate generated by the addition
of triphenylphosphine to dialkyl acetylenedicarboxylates is
trapped by alizarin to produce alkyl 6,11-dihydro-12-
hydroxy-2,6,11-trioxo-2H-naphtho[2,3-g]chromene-4-car-
boxylates in good yields. When ethyl propiolate was used,
the reaction afforded ethyl 6,11-dihydro-6,11-dioxoan-
thra[1,2-d][1,3]-dioxole-2-acetate. The reaction of dialkyl
acetylenedicarboxylates, alizarin, and trialkyl phosphites
produced dialkyl 2-(dialkoxyphosphoryl)-3-(9,10-dihydro-
1-hydroxy-9,10-dioxoanthracen-2-yloxy)succinates.
[9–14], we report a simple one-pot synthesis of function-
alized alizarin derivatives. Thus, the reaction of alizarin
with dialkyl acetylenedicarboxylates in the presence of
Ph3P produced functionalized dihydro-2H-naphtho[2,3-g]-
chromenes in good yields. When ethyl propiolate was used,
the reaction afforded ethyl 6,11-dihydro-6,11-dioxoan-
thra[1,2-d][1,3]-dioxole-2-acetate. The reaction of dialkyl
acetylenedicarboxylates, alizarin, and trialkyl phosphites
produced phosphorylated alizarins.
Keywords Alizarin Á Acetylenic esters Á
Triphenylphosphine Á Trialkyl phosphites
Results and discussion
The reaction of alizarin, dialkyl acetylenedicarboxylates 1,
and Ph3P in toluene proceeded smoothly under reflux and
afforded alkyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-
naphtho[2,3-g]chromene-4-carboxylates 3a, 3b in good
yields. When ethyl propiolate (4a) and ethyl phenylpropi-
olate (4b) were employed as the acetylenic component,
the reaction produced ethyl 6,11-dihydro-6,11-dioxoan-
thra[1,2-d][1,3]-dioxole-2-acetate (5a) and ethyl 6,11-
dihydro-6,11-dioxo-2-phenylanthra[1,2-d][1,3]-dioxole-
2-acetate (5b), respectively (Scheme 1).
Introduction
Alizarin (1,2-dihydroxyanthraquinone) is the parent com-
pound for a large palette of anthraquinone dyes. Hydroxy-
substituted 9,10-anthraquinones are important in the dye
industry, biology, and pharmaceutical chemistry. Alizarin
derivatives have been the subject of many studies [1, 2]. In
recent years, the reactions of phenols [3–5], dihydroxy-
benzenes [6, 7], and 1,5-dihydroxyanthraquinone [8] with
the zwitterionic intermediates derived from triphenyl-
phosphine (Ph3P) and dialkyl acetylenedicarboxylates have
been reported.
The reaction of alizarin with 1 in the presence of trialkyl
phosphites 6 in toluene under reflux produced dialkyl
2-(dialkoxyphosphoryl)-3-(9,10-dihydro-1-hydroxy-9,10-
dioxoanthracen-2-yloxy)succinates 7a–7d, together with
2-alkoxy-1-hydroxyanthracene-9,10-diones 8a, 8b (Scheme 2).
Compounds 8 have been reported previously [15].
In continuation of our current interest in the develop-
ment of new routes to heterocyclic and carbocyclic systems
The structures of compounds 3, 5, and 7 were deduced
1
from their high-field H and 13C NMR, IR, and UV-Vis
absorption spectral data. The mass spectra of these com-
pounds exhibited molecular ion peaks at the appropriate
m/z values. The 31P NMR spectra of phosphonates 7 con-
firmed the presence of phosphonate groups.
I. Yavari (&) Á L. Azad Á T. Sanaeishoar
Department of Chemistry, Science and Research Branch,
Islamic Azad University, Ponak, Tehran, Iran
e-mail: yavarisa@modares.ac.ir
123

644
I. Yavari et al.
Scheme 1
H
H
O
O
O
O
CO2R
+
OH
O
O
Toluene
Reflux
PPh3
+
CO2R
O
O
CO2R
R
R
1a Me
2
3a
Me
1b
Et
3b Et
CH2CO2Et
R
O
H
O
O
CO2Et
O
O
OH
Toluene
Reflux
PPh3
+
+
R
O
O
R
4a H
4b Ph
R
2
5a H
5b Ph
protons. The 13C NMR spectrum of 5a showed 19 reso-
nances in agreement with the proposed structure.
H
O
O
CO2R
+
OH
1
The H NMR spectrum of 7a showed two doublets for
Toluene
Reflux
2
(R'O)3P
+
3
the two diastereotopic methoxy (d = 3.55 ppm, JHP
=
3
CO2R
11.1 Hz and d = 3.65 ppm, JHP = 11.1 Hz) groups. The
two singlets at 3.88 and 4.14 ppm belong to the ester
methoxy protons. Although the presence of the 31P nucleus
complicates both the 1H and 13C NMR spectra of 7a–7d, it
helps in the assignment of the signals by long-range cou-
O
R'
6a Me
6b Et
R
2
1a Me
1b Et
1
pling with H and 13C nuclei.
H
H
O
O
O
CO2R
O
O
3
Observation of JHH = 11.6 Hz for the vicinal methine
O
OR'
P
OR'
protons in 7a indicates the dominance of the anti-
arrangement. Since compound 7a possesses two stereo-
genic centers, two diastereoisomers with anti-HCCH
arrangements are possible (Scheme 3). The observation of
3JCP = 21 Hz for the carbonyl carbon atom of the
CO2Me group is in agreement with the (2S,3R) or (2R,3S)
diastereoisomer.
+
CO2ROR'
O
O
R
R'
R'
8a Me
8b Et
7a
7b
7c
7d
Me Me
Et Me
Me Et
Et Et
Scheme 2
In conclusion, we have reported a one-pot synthesis of
functionalized dihydro-2H-naphtho[2,3-g]chromenes from
alizarin and dialkyl acetylenedicarboxylates in the presence
of Ph3P. When ethyl propiolate was used, the reaction led
to ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-
2-acetate. The reaction of dialkyl acetylenedicarboxylates,
alizarin, and trialkyl phosphites produced phosphorylated
dialkyl 3-(9,10-dihydro-1-hydroxy-9,10-dioxoanthracen-2-
yloxy)succinates.
The 1H NMR spectrum of 3a in CDCl3 exhibited a
singlet at d = 4.10 ppm for the methoxy protons along
with resonances at 7.88–8.40 ppm for the aromatic protons.
The OH proton appears as a singlet at 13.05 ppm, as a
result of strong intramolecular hydrogen bonding. The 13C
NMR spectrum of 3a showed 19 distinct resonances in
agreement with the proposed structure. The H and 13C
1
NMR spectra of 3b were similar to those of 3a except for
the alkoxy moieties, which exhibited characteristic signals
with appropriate chemical shifts.
Experimental
1
The H NMR spectrum of 5a in CDCl3 showed two
signals at d = 1.30 and 4.25 ppm for the ethoxy protons,
along with resonances at 7.14–8.33 ppm for the aromatic
All chemicals used in this study were purchased from
Merck and were used without further purification. Melting
123

Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles
645
Scheme 3
O
O
OH
Z
CO2Me
H
H
O
(MeO)2(O)P
H
(MeO)2(O)P
H
=
Z
CO2Me
Z
CO2Me
CO2Me
(2S,3R)-7a or (2R,3S)-7a
(2S,3S)-7a or (2R,3R)-7a
8.31–8.39 (2H, m, CH), 8.73 (1H, s, CH), 13.02 (1H, s,
OH) ppm; 13C NMR (CDCl3): d = 14.5 (Me), 63.5
(CH2O), 117.3 (C), 117.8 (CH), 121.2 (C), 123.3 (CH),
127.6 (CH), 128.1 (CH), 128.5 (C), 133.5 (C), 134.1 (C),
134.8 (CH), 135.8 (CH), 142.6 (C), 147.6 (C–O), 151.1
(C–O), 158.2, 163.3, 181.2, 189.9 (4C=O) ppm.
points were measured on an Electrothermal 9100 appara-
tus. Elemental analyses for C and H were performed using
a Heraeus CHN-O-Rapid analyzer. UV spectra were taken
on a Shimadzu UV-160A spectrometer. The experimental
data were in good agreement with the calculated values. 1H
and 13C NMR spectra (CDCl3) were measured with a
Bruker DRX-300 Avance spectrometer. IR spectra were
recorded on a Shimadzu IR-460 spectrometer. Mass spectra
were recorded on a Finnigan-Mat 8430 spectrometer
operating at an ionization potential of 70 eV. Chromatog-
raphy columns were prepared from Aldrich silica gel
(70–230 mesh).
General procedure for the preparation of compounds 5
To a stirred solution of 0.26 g of Ph3P (1 mmol) and 0.22 g
of alizarin (1 mmol) in 5 cm3 of toluene was added drop-
wise a mixture of the propiolate ester (1 mmol) in 2 cm3 of
toluene at r.t. The reaction mixture was then refluxed for
24 h. The solvent was removed under reduced pressure,
and the residue was separated on silica gel column chro-
matography (Merck 230–400 mesh) using hexane-AcOEt
(3:1) as eluent.
General procedure for the preparation of compounds 3
To a stirred solution of 0.26 g of Ph3P (1 mmol) and 0.22 g
of alizarin (1 mmol) in 5 cm3 of toluene was added drop-
wise a mixture of the dialkyl acetylenedicarboxylate
(1 mmol) in 2 cm3 of toluene at r.t. The reaction mixture
was then refluxed for 24 h. The product was filtered and
washed with cold Et2O.
Ethyl 6,11-dihydro-6,11-dioxoanthra[1,2-d][1,3]-dioxole-
2-acetate (5a, C19H14O6)
Yellow powder; yield: 0.23 g (97%); m.p.: 139–141 °C; UV
(EtOH, 95%): kmax (e) = 410 (4,110) nm (mol-1 cm2); IR
(KBr): vꢀ = 1,732 (C=O), 1,224 (C–O) cm-1; EI–MS:
m/z = 338 (M?, 8), 293 (18), 239 (100), 132 (8), 57 (21);
Methyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naph-
tho[2,3-g]chromene-4-carboxylate (3a, C19H10O7)
3
1H NMR (CDCl3): d = 1.30 (3H, t, JHH = 7.1 Hz, Me),
Green powder; yield: 0.33 g (95%); m.p.: 248–250 °C; UV
(EtOH, 95%): kmax (e) = 403 (6,105) nm (mol-1 cm2); IR
(KBr): vꢀ = 3,405 (OH), 1,735 (C=O) cm-1; EI–MS:
m/z = 350 (M?, 10), 321 (15), 291 (100), 262 (35), 239
3.16 (2H, (AB)X system, JAB = 16 Hz, JAX = 6.5 HZ,
3
JBX = 3.5 Hz, CH2), 4.25 (2H, q, JHH = 7.1 Hz, CH2O),
6.88 (1H, dd, 3J = 6.5 Hz, 3J = 3.5 Hz, CH), 7.15 (1H, d,
3JHH = 8 Hz, CH), 7.77–7.83 (2H, m, CH), 8.00 (1H, d,
3JHH = 8 Hz, CH), 8.26–8.35 (2H, m, CH) ppm; 13C NMR
(CDCl3): d = 14.3 (Me), 45.4 (CH2), 61.4 (CH2O), 99.6
(CH), 119.4 (CH), 124.2 (CH), 127.4 (CH), 127.6 (CH),
127.7 (C), 130.1 (C), 134.0 (C), 134.2 (CH), 134.3 (CH),
134.4 (C), 148.2 (C–O), 154.3 (C–O), 167.2, 182.0, 182.0
(3C=O) ppm.
1
(41), 210 (11); H NMR (CDCl3): d = 4.11 (3H, s, MeO),
7.19 (1H, s, CH), 7.87–7.90 (2H, m, CH), 8.33–8.39 (2H,
m, CH), 8.73 (1H, s, CH), 13.04 (1H, s, OH) ppm; 13C
NMR (CDCl3): d = 54.3 (MeO), 117.6 (C), 117.7 (CH),
121.3 (C), 123.5 (CH), 127.9 (CH), 128.3 (CH), 128.9 (C),
133.5 (C), 134.7 (C), 134.8 (CH), 135.8 (CH), 142.2 (C),
147.5 (C–O), 151.2 (C–O), 158.2, 163.2, 181.1, 189.9
(4 C=O) ppm.
Ethyl 6,11-dihydro-6,11-dioxo-2-phenylanthra-
[1,2-d][1,3]-dioxole-2-acetate (5b, C25H18O6)
Ethyl 6,11-dihydro-12-hydroxy-2,6,11-trioxo-2H-naph-
tho[2,3-g]chromene-4-carboxylate (3b, C20H12O7)
Yellow powder; yield: 0.30 g (73%); m.p.: 145–147 °C; UV
(EtOH, 95%): kmax (e) = 409 (3,514) nm (mol-1 cm2); IR
(KBr): vꢀ = 1,740 (C=O), 1,226 (C–O) cm-1; EI–MS:
m/z = 414 (M?, 7), 369 (17), 239 (100), 132 (20), 77
Green powder; yield: 0.34 g (94%); m.p.: 224–226 °C; UV
(EtOH, 95%): kmax (e) = 400 (6,080) nm (mol-1 cm2); IR
(KBr): vꢀ = 3,410 (OH), 1,737 (C=O) cm-1; EI–MS:
m/z = 364 (M?, 9), 335 (17), 291 (100), 262 (38), 239
(43), 210 (8); 1H NMR (CDCl3): d = 1.52 (3H, t,
1
3
(34); H NMR (CDCl3): d = 1.52 (3H, t, JHH = 7.1 Hz,
Me), 3.45 (2H, ABq, JAB = 10.5 Hz, DmAB = 6 Hz, CH2),
4.07 (2H, q, JHH = 7.1 Hz, CH2O), 7.16 (1H, d,
3
3
3JHH = 7.1 Hz, Me), 4.55 (2H, q, JHH = 7.1 Hz,
3JHH = 8 Hz, CH), 7.35–7.47 (5H, m, CH), 7.69–7.73
CH2O), 7.17 (1H, s, CH), 7.84–7.91 (2H, m, CH),
123

646
I. Yavari et al.
(2H, m, CH), 7.76–7.81 (1H, m, CH), 7.98 (1H, d,
3JHH = 8 Hz, CH), 8.26–8.32 (1H, m, CH) ppm; 13C
NMR (CDCl3): d = 14.3 (Me), 45.4 (CH2), 61.4 (CH2O),
112.8 (C), 117.0 (CH), 119.3 (CH), 124.3 (CH), 125.4
(2CH), 127.3 (CH), 127.6 (CH), 127.7 (C), 129.0 (2CH),
130.1 (C), 134.0 (C), 134.2 (CH), 134.3 (CH), 134.4 (C),
139.0 (C), 148.2 (C–O), 154.3 (C–O), 167.2, 182.0, 182.0
(3C=O) ppm.
(CDCl3): d = 1.15 (3H, t, 3JHH = 7.1 Hz, Me), 1.35 (3H, t,
3
3JHH = 7.1 Hz, Me), 3.60 (3H, d, JHP = 11.1 Hz, MeO),
3
3.65 (3H, d, JHP = 11.1 Hz, MeO), 4.07-4.38 (5H, m,
CH2O, CH), 4.78 (1H, dd, 3JHH = 11.8 Hz, 3JHP = 6.7 Hz,
CH), 7.79-7.86 (4H, m, CH), 8.28-8.35 (2H, m, CH), 12.95
(1H, s, OH) ppm; 13C NMR (CDCl3): d = 14.3 (Me), 14.4
1
2
(Me), 46.2 (d, JCP = 130.0 Hz, CH), 46.3 (d, JCP
=
2
4.0 Hz, CH), 53.3 (d, JPC = 6.7 Hz, MeO), 53.7 (d,
2JPC = 7.2 Hz, MeO), 61.3 (CH2O), 62.2 (CH2O), 117.3
(C), 122.0 (CH), 127.2 (CH), 127.7 (CH), 127.8 (CH), 133.6
(C), 134.1 (C), 134.3 (CH), 135.2 (CH), 136.7 (C), 152.7
(C–O), 155.6 (C–O), 168.7 (d, 2JCP = 6.9 Hz, C=O), 171.4
(d, 3JCP = 20.9 Hz, C=O), 181.9 (C=O), 189.5 (C=O) ppm;
31P NMR (CDCl3): d = 22.71 ppm.
General procedure for the preparation of compounds
7 and 8
To a stirred solution of trialkyl phosphite (1 mmol) and
0.44 g of alizarin (2 mmol) in 5 cm3 of toluene was added
dropwise a mixture of the dialkyl acetylenedicarboxylate
(1 mmol) in 2 cm3 of toluene at r.t. The reaction mixture
was then refluxed for 24 h. The precipitate (compound 8)
was filtered and washed with cold Et2O. Then, the mother
liquid was evaporated under reduced pressure to give a
residue, which was separated on silica gel column chro-
matography (Merck 230–400 mesh) using hexane-AcOEt
(1:1) as eluent to afford compound 7.
Diethyl 2-(dimethoxyphosphoryl)-3-(9,10-dihydro-1-
hydroxy-9,10-dioxoanthracen-2-yloxy)butanedioate
(7c, C24H25O11P)
Yellow powder; yield: 0.34 g (67%); m.p.: 130–132 °C; UV
(EtOH, 95%): kmax (e) = 415 (2,990) nm (mol-1 cm2); IR
(KBr): vꢀ = 1,738 (C=O), 1,265 (P=O) cm-1; EI–MS:
m/z = 520 (M?, 5), 491 (100), 293 (33), 240 (55), 224
(15), 167 (9), 137 (7), 45 (80), 29 (65); 1H NMR (CDCl3):
3
Dimethyl 2-(dimethoxyphosphoryl)-3-(9,10-dihydro-1-
hydroxy-9,10-dioxoanthracen-2-yloxy)butanedioate
(7a, C22H21O11P)
d = 1.14 (3H, t, JHH = 7.1 Hz, Me), 1.46 (3H, t,
3JHH = 7.1 Hz, Me), 3.65 (3H, s, MeO), 3.87 (3H, s,
MeO), 3.88-4.10 (3H, m, CH2O, CH), 4.29–4.63 (2H, m,
3
3
Yellow powder; yield: 0.33 g (67%); m.p.: 137–139 °C; UV
(EtOH, 95%): kmax (e) = 413 (2,350) nm (mol-1 cm2); IR
(KBr): vꢀ = 1,739 (C=O), 1,273 (P=O) cm-1; EI–MS:
m/z = 492 (M?, 3), 477 (9), 463 (100), 249 (29), 240 (51),
CH2O), 4.75 (1H, dd, JHH = 11.6 Hz, JHP = 6.2 Hz,
CH), 7.79–7.86 (4H, m, CH), 8.28–8.34 (2H, m, CH), 12.98
(1H, s, OH) ppm; 13C NMR (CDCl3): d = 14.3 (Me), 14.4
1
2
(Me), 46.2 (d, JCP = 131.0 Hz, CH), 46.3 (d, JCP
4.1 Hz, CH), 53.0 (MeO), 53.4 (MeO), 62.8 (d,
=
1
224 (14), 167 (10), 132 (8), 109 (7), 31 (55); H NMR
3
2
(CDCl3): d = 3.55 (3H, d, JHP = 11.1 Hz, MeO), 3.65
2JPC = 6.2 Hz, CH2O), 63.3 (d, JPC = 6.9 Hz, CH2O),
(3H, d, 3JHP = 11.1 Hz, MeO), 3.88 (3H, s, MeO), 4.06 (1H,
117.5 (C), 122.1 (CH), 127.2 (CH), 127.7 (CH), 127.8 (CH),
133.5 (C), 134.1 (C), 134.3 (CH), 135.3 (CH), 136.3 (C),
152.5 (C–O), 155.5 (C–O), 169.4 (d, 2JCP = 6.7 Hz, C=O),
3
2
dd, JHH = 11.6 Hz, JHP = 21.2 Hz, CH), 4.14 (3H, s,
MeO), 4.75 (1H, dd, 3JHH = 11.6 Hz, 3JHP = 6.4 Hz, CH),
7.80-7.84 (4H, m, CH), 8.27-8.39 (2H, m, CH), 12.95 (1H, s,
3
171.5 (d, JCP = 21.2 Hz, C=O), 181.7 (C=O), 189.4
(C=O) ppm; 31P NMR (CDCl3): d = 22.69 ppm.
1
OH) ppm; 13C NMR (CDCl3): d = 45.9 (d, JCP
=
2
130.4 Hz, CH), 46.4 (d, JCP = 4.0 Hz, CH), 53.0 (MeO),
Diethyl 2-(diethoxyphosphoryl)-3-(9,10-dihydro-1-
hydroxy-9,10-dioxoanthracen-2-yloxy)butanedioate
(7d, C26H29O11P)
2
53.2 (MeO), 53.8 (d, JPC = 7.77 Hz, MeO), 54.2 (d,
2JPC = 6.21 Hz, MeO), 117.4 (C), 122.2 (CH), 127.2 (CH),
127.7 (CH), 127.8 (CH), 133.6 (C), 134.1 (C), 134.3 (CH),
135.2 (CH), 136.3 (C), 152.5 (C–O), 155.5 (C–O), 169.3 (d,
Yellow powder; yield: 0.36 g (65%); m.p.: 127–125 °C; UV
(EtOH, 95%): kmax (e) = 414 (3,100) nm (mol-1 cm2); IR
(KBr): vꢀ = 1,734 (C=O), 1,255 (P=O) cm-1; EI–MS:
m/z = 548 (M?, 7), 519 (100), 276 (26), 251 (15), 240
(56), 178 (11), 137 (8), 146 (9), 45 (87), 29 (63); 1H NMR
(CDCl3): d = 1.11 (3H, t, 3JHH = 7.1 Hz, Me), 1.21 (3H, t,
3JHH = 7.1 Hz, Me), 1.33 (3H, t, 3JHH = 7.1 Hz, Me), 1.50
(3H, t, 3JHH = 7.1 Hz, Me), 3.78-4.22 (5H, m, CH2O, CH),
3
2JCP = 6.0 Hz, C=O), 171.8 (d, JCP = 21.0 Hz, C=O),
181.8 (C=O), 189.4 (C=O) ppm; 31P NMR (CDCl3):
d = 22.47 ppm.
Diethyl 2-(dimethoxyphosphoryl)-3-(9,10-dihydro-
1-hydroxy-9,10-dioxoanthracen-2-yloxy)butanedioate
(7b, C24H25O11P)
3
Yellow powder; yield: 0.34 g (67%); m.p.: 145–148 °C; UV
(EtOH, 95%): kmax (e) = 412 (2,455) nm (mol-1 cm2); IR
(KBr): vꢀ = 1,740 (C=O), 1,275 (P=O) cm-1; EI–MS:
m/z = 520 (M?, 8), 505 (11), 491 (100), 276 (30), 251
(14), 240 (50), 178 (10), 146 (7), 109 (8), 31 (56); 1H NMR
4.33 (2H, q, JHH = 7.1 Hz, CH2O), 4.43 (2H, q,
3
3JHH = 7.1 Hz, CH2O), 4.79 (1H, dd, JHH = 11.7 Hz,
3JHP = 6.3 Hz, CH), 7.77–7.87 (4H, m, CH), 8.25–8.37
(2H, m, CH), 12.98 (1H, s, OH) ppm; 13C NMR (CDCl3):
d = 14.3 (Me), 14.4 (Me), 15.0 (Me), 15.0 (Me), 46.2 (d,
123

Synthesis of new functionalized alizarins from alizarin, acetylenic esters, and phosphorus nucleophiles
2
647
1JCP = 132.0 Hz, CH), 46.3 (d, JCP = 4.1 Hz, CH), 62.1
(CH2O), 62.2 (CH2O), 63.1 (d, 2JPC = 7.1 Hz, CH2O), 63.3
4. Baharfar R, Vahdat SM, Hakimabadi FG (2009) Monatsh Chem
140:489
5. Yavari I, Feiz-Javadian F (2006) Phosphorus. Sulfur Silicon Relat
Elem 181:1011
2
(d, JPC = 7.8 Hz, CH2O), 117.4 (C), 122.1 (CH), 127.1
(CH), 127.7 (CH), 127.8 (CH), 133.5 (C), 134.1 (C), 134.3
(CH), 135.2 (CH), 136.7 (C), 152.7 (C–O), 155.6 (C–O),
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2
3
168.7 (d, JCP = 6.5 Hz, C=O), 171.4 (d, JCP = 21.0 Hz,
C=O), 181.8 (C=O), 189.6 (C=O) ppm; 31P NMR (CDCl3):
d = 22.67 ppm.
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12. Yavari I, Samzadeh-Kermani AR (1984) Tetrahedron Lett
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