Three-Component reaction of triphenylphosphine, acetylenic esters, and 6-Aminouracil or 6-Amino- N,N'- Dimethyluracil

Article abstract of DOI:10.1080/00397911.2011.627105

Protonation of the reactive 1:1 intermediate produced in the reaction of acetylenic esters and triphenylphosphine by 6-aminouracil or 6-amino-N,N'-dimethyluracil leads to vinylphosphonium salts, which undergo Michael addition with the conjugate base of th

Full text of DOI:10.1080/00397911.2011.627105

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Three-Component Reaction of
Triphenylphosphine, Acetylenic Esters,
and 6-Aminouracil or 6-Amino-N,N′-
dimethyluracil
Razieh Mohebat a , Mohammad Anary-Abbasinejad b , Sohrab
Hajmohammadi a & Alireza Hassanabadi c
a Department of Chemistry , Islamic Azad University , Yazd Branch ,
Yazd , Iran
b Department of Chemistry , Rafsanjan Vali-e-Asr University ,
Rafsanjan , Iran
c Department of Chemistry , Islamic Azad University , Zahedan
Branch , Zahedan , Iran
Accepted author version posted online: 29 Feb 2012.Published
online: 25 Jul 2013.
To cite this article: Razieh Mohebat , Mohammad Anary-Abbasinejad , Sohrab Hajmohammadi &
Alireza Hassanabadi (2013) Three-Component Reaction of Triphenylphosphine, Acetylenic Esters,
and 6-Aminouracil or 6-Amino-N,N′-dimethyluracil, Synthetic Communications: An International
Journal for Rapid Communication of Synthetic Organic Chemistry, 43:21, 2833-2840, DOI:
10.1080/00397911.2011.627105
To link to this article: http://dx.doi.org/10.1080/00397911.2011.627105
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Synthetic Communications1, 43: 2833–2840, 2013
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2011.627105
THREE-COMPONENT REACTION OF
TRIPHENYLPHOSPHINE, ACETYLENIC ESTERS, AND
6-AMINOURACIL OR 6-AMINO-N,N’-DIMETHYLURACIL
Razieh Mohebat,1 Mohammad Anary-Abbasinejad,2
Sohrab Hajmohammadi,1 and Alireza Hassanabadi3
1Department of Chemistry, Islamic Azad University, Yazd Branch,
Yazd, Iran
2Department of Chemistry, Rafsanjan Vali-e-Asr University, Rafsanjan, Iran
3Department of Chemistry, Islamic Azad University, Zahedan Branch,
Zahedan, Iran
GRAPHICAL ABSTRACT
Abstract Protonation of the reactive 1:1 intermediate produced in the reaction of acetylenic
esters and triphenylphosphine by 6-aminouracil or 6-amino-N,N0-dimethyluracil leads to
vinylphosphonium salts, which undergo Michael addition with the conjugate base of the
NH acid to produce highly fanctionalized, salt-free phosphorus ylides in excellent yields.
Keywords Acetylenic esters; 6-amino-N,N0-dimethyluracil; 6-aminouracil; phosphorus
ylides; triphenylphosphine
Received July 27, 2011.
Address correspondence to Razieh Mohebat, Department of Chemistry, Islamic Azad University,
Yazd Branch, P.O. Box 89195-155, Yazd, Iran. E-mail: rozitakalami@yahoo.com
2833

2834
R. MOHEBAT ET AL.
INTRODUCTION
Ylides are important reagents in synthetic organic chemistry, especially in
the synthesis of naturally occurring products and compounds with biological and
pharmacological activity.[1] Phosphorus ylides are reactive systems that take part
in many reactions of value in organic synthesis.[2–8] Several methods have been
developed for the preparation of phosphorus ylides. These ylides are usually pre-
pared by treatment of an appropriate phosphonium salt with a base; the correspond-
ing phosphonium salts are usually obtained from the phosphine and an alkyl
halide.[2,3] Phosphonium salts are also prepared by Michael addition of phosphorus
nucleophiles to activated olefins.[2] Reaction of acetylenic esters with triphenylpho-
sphine in the presence of an acidic hydrogen-containing organic compound has also
been reported to produce phosphorus ylides.[9] In continuation of our work on the
reactions between trivalent phosphorus nucleophiles and electron-deficient acetylenic
compounds in the presence of organic N-H, O-H, or C-H acids,[10–21] here we report
the results of our study on the reaction between triphenylphosphine and electron-
deficient acetylenic esters in the presence of 6-amino-N,N0-dimethyluracil (Scheme 1).
Thus the reaction between dimethyl acetylenedicarboxylate (DMAD) or
diethyl acet ylenedicarboxylate (DEAD) with 6-amino-N,N0-dimethyl uracil in the
presence of triphenylphosphine afforded alkyl-1,3-dimethyl-2,4,7-trioxo-6-
(triphenyl-k5-phosph anylidene)-1,2,3,4,5,6,7,8-octahydropyrido[2,3-d]pyrimidine-5-
carboxylate 4a and b in good yields (Scheme 2).
The mass spectra of the ylides 4 are fairly similar and display molecular ion
peaks.
1
The H NMR spectrum of 4a shows three sharp lines (d ¼ 3.06, 3.20, and
3.15 ppm) corresponding to the protons of the methyl groups and methoxy protons
respectively. There was a doubled signal for the methine proton at 3.57
(3JHP ¼ 10.5 Hz). The aromatic protons resonated between 7.31 and 7.67 ppm. A
broad signal was observed at d ¼ 9.32 ppm for NH proton which disappeared after
Scheme 1. Condensation of acetylenic esters and 6-amino-N,N0-dimethyl uracil in the presence of
triphenylphosphine.

6-AMINOURACIL
2835
Scheme 2. Condensation of DMAD or DEAD and 6-amino-N,N0-dimethyl uracil in the presence of
triphenylphosphine.
a few drops of D2O were added to dimethylsulfoxide (DMSO) solution of 4a. The
31P NMR spectrum of compound 4a consists of one signal at 20.15. This shift is simi-
lar to those observed for other stable phosphorus ylides.[22,23] 13 C NMR spectrum
of compound 4a shows 15 distinct signals, which is consistent with the proposed
structure. The infrared (IR) spectrum of compound 4a also supported the suggested
structure, and strong absorption bands were observed at 3025, 1719, and 1690 cmꢀ1
respectively for the NH and carbonyl groups.
On the basis of the well-established chemistry of trivalent phosphorus nucleo-
philes,[2,3,11] it is reasonable to assume that ylides 4 result from the initial addition
of triphenylphosphine to the acetylenic ester and subsequent protonation of the 1:1
adduct by 6-amino-N,N0-dimethyluracil. Then, the positively charged ion intermediate
Scheme 3. Suggested mechanism for formation of ylides 4.

2836
R. MOHEBAT ET AL.
Scheme 4. Condensation of DTAD and 6-amino-N,N0-dimethyl uracil in the presence of triphenylphosphine.
8 is attacked by the conjugate anion of 6-amino-N,N0-dimethyluracil 9 to form the
intermediate 10. Compound 11, which followed by addition of the amino to carbonyl
group, then loses an alkoxide ion and cyclizes to phosphorane 4 (Scheme 3).
Under similar conditions as these reactions, triphenylphosphine reacted with
DTAD in the presence of 6-amino-N,N0-dimethyluracil to produce phosphorane 5
in 73% yield (Scheme 4).
NMR spectra of compound 5 in d6-DMSO show that this compound, in con-
trast to ylides 4a and 4b, is stable and does not cyclize to phosphorane 4 even at
refluxing acetonitrile because t-butyl group is a hindrance. The three-component
reaction of acetylenic esters, triphenylphosphine, and 6-aminouracil also leads to
the phosphorus ylides 7a and b (Scheme 5).
The mass spectra of the ylides 7 are fairly similar and display molecular ion peaks.
1
The H NMR spectrum of compound 7a showed two singlets at 3.05 and
3.65 ppm for methoxy protons. There was a doubled signal for the methine proton
at 4.82 (3JHP ¼ 10.5 Hz). The aromatic protons resonated between 7.60 and
7.90 ppm. A broad singlet with the integral of 2 was observed at d ¼ 10.98 ppm for
NH2 protons, and two single signals we observed at 7.59 and 7.89 ppm for NH pro-
tons that disappeared after addition of a few drops of D2O to the d6-DMSO solution
of compound 7a. The 31P NMR spectrum of compound 7a displays two signals at
24.29 ppm. 13C NMR spectrum of compound 7a showed 14 distinct signals in
accordance with the proposed structure.
Scheme 5. Three-component reaction of triphenylphosphine, acetylenic esters, and 6-aminouracil.

6-AMINOURACIL
2837
In summary, phosphorus ylides may be prepared by a simple, one-pot, three-
component reaction of acetylenic esters, triphenylphosphine, and 6-amino-N,N0-
dimethyluracil or 6-aminouracil. The present method has the advantage that not
only the reaction is performed under neutral conditions but also the substances
can be mixed without any activation or modification.
EXPERIMENTAL
Melting points were determined with an Electrothermal 9100 apparatus.
Elemental analyses were performed at the analytical laboratory of the Science and
Research Unit of Islamic Azad University. Mass spectra were recorded on a
Finnigan-Mat 8430 mass spectrometer operating at an ionization potential of
70 eV. Infrared (IR) spectra were recorded on a Shimadzu IR-470 spectrometer.1H,
13C and 31P NMR spectra were recorded on a Bruker DRX-500 Avance spec-
trometer in d6-DMSO using tetramethylsilane (TMS) as internal standard or 85%
H3PO4 as external standard. The chemicals used in this work were purchased from
Fluka (Buchs, Switzerland) and were used without further purification.
General Procedure for Preparation of Compounds 4a, 4b, 5, 7a, and 7b
To a magnetically stirred solution of uracil derivatives 3 or 6 (1 mmol) in 10 mL
tetrahydrofuran (THF) and triphenylphosphine 1 (1 mmol) was added a mixture of
acetylenic esters 2 (1 mmol) in 2 mL THF at room temperature. The reaction mixture
was then allowed to stir for 24 h. The solvent was evaporated at reduced pressure, and
the residue was purified by silica-gel column chromatography using hexane–ethyl acet-
ate as eluent. The solvent was removed under reduced pressure to afford the product.
Methyl 1,3-dimethyl-2,4,7-trioxo-6-(triphenyl-k5-phosphanylidene)-1,2,3,
4,5,6,7,8-octahydro pyrido[2,3-d]pyrimidine-5-carboxylate (4a). White power;
yield (90%); mp ¼ 173–175 ꢁC. IR (KBr) (nmax cmꢀ1): 3025 (NH), 1719, and 1690
=
(C O). Analyst: calcd. for C29H26N3O5P: C, 66.03; H, 4.97; N, 7.97%. Found: C,
65.87; H, 5.20; N, 8.06%, MS (m=z, %): 527 (Mþ, 5). H NMR (500 MHz, d6-
1
DMSO): d 3.06 and 3.20 (6H, 2 s, 2NCH3), 3.15 (3H, s, OCH3), 3.57 (1H, d,
3JHP ¼ 10.5 Hz, CH), 7.31–7.67 (15H, m, aromatic), 9.32 (1H, br, NH) ppm. 13C
NMR (125.7 MHz, d6-DMSO): d 29.71 and 29.90 (2NCH3), 38.40 (CH, d,
2
JPC ¼ 14.9 Hz), 40.44 (C P, d, 1JPC ¼ 125 Hz), 51.34 (OCH3), 84.41
=
(d,3JPC ¼ 12 Hz, C C-NH), 124.81 (Cipso, d, JPC ¼ 91.0 Hz), 129.38 (Cmeta, d,
1
=
3JPC ¼ 11.8 Hz), 132.90 (Cpaea), 133.88 (Cortho
31
,
d, JPC ¼ 9.9 Hz), 148.17
2
2
=
=
=
(C C-NH), 151.17 and 160.76 (2C O), 165.73 (d, JPC ¼ 15.3 Hz, C O), 174.83
=
(C O) ppm. P NMR (d6-DMSO): d ¼ 20.15 ppm.
Ethyl 1,3-dimethyl-2,4,7-trioxo-6-(triphenyl-k5-phosphanylidene)-1,2,3,4,
5,6,7,8-octahydro pyrido[2,3-d]pyrimidine-5-carboxylate (4b). White power;
yield (85%); mp ¼ 188–190 ꢁC. IR (KBr) (nmax cmꢀ1): 3055 (N-H), 1725, 1692
=
(C O). Analyst: calcd. for C30H28N3O5P: C, 66.54; H, 5.21; N, 7.76%. Found: C,
66.75; H, 5.40; N, 7.59%, MS (m=z, %): 541 (Mþ, 3). H NMR (500 MHz, d6-
1
DMSO): d 0.73 (3 H, t,3JHH ¼ 7.1 Hz, CH3), 3.08 and 3.32 (6H, 2 s, 2NCH3), 3.55
3
3
(1H, d, JHP ¼ 10.5 Hz, CH), 3.77 (2H, m, JHH ¼ 7 HZ, OCH2), 7.32–7.70 (15H,

2838
R. MOHEBAT ET AL.
m, aromatic), 9.18 (1H, br, NH) ppm. 13C NMR (125.7 MHz, d6-DMSO): d 13.88
2
=
(CH3), 27.95 and 30.17 (2NCH3), 38.43 (CH, d, JPC ¼ 14.9 Hz), 41.32 (C P,
d, JPC ¼ 125 Hz), 60.40 (OCH2), 84.40 (d,3JPC ¼ 12 Hz, C C-NH), 125.12 (C
,
,
1
ipso
=
d, JPC ¼ 91.0 Hz), 129.36 (Cmeta, d, JPC ¼ 11.8 Hz), 132.91 (Cpaea), 133.67 (Cortho
31
1
3
2
2
=
=
d, JPC ¼ 9.9 Hz), 148.33 (C C-NH), 151.27 and 160.78 (2C O), 165.42 (d, JPC
¼
=
=
15.3 Hz, C O), 174.89 (C O) ppm. P NMR (d6-DMSO): d ¼ 20.12 ppm.
Di-tert-butyl-2-(6-amino-1,3 dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyridin-
5-yl)-3-(triphenyl-k5-phosphanylidene)succinate (5). White power; yield (73%);
mp ¼ 179–181 ꢁC. IR (KBr) (nmax cmꢀ1): 3345 (NH2), 1722, 1605 (C O). Analyst:
=
calcd. for C36H42N3O6P: C, 67.17; H, 6.58; N, 6.53%. Found: C, 66.90; H, 6.71;
1
N, 6.64%. MS (m=z, %): 643 (Mþ, 8). H NMR (500 MHz, d6-DMSO): d 0.84 and
3
1.45 (18H, 2 s, 2 t-Bu), 3.06 and 3.38 (6H, 2 s, 2NCH3), 4.15 (1H, d, JHP ¼ 18.8 Hz,
Hz, CH), 7.20 (2H, br, NH2), 7.48–7.67 (15H, m, aromatic), 13C NMR (125.7 MHz,
d6-DMSO): d 25.99 and 28.78 (6CH3), 28.24 and 29.00 (2NCH3), 38.60 (CH, d,
2
1
=
JPC ¼ 13.8 Hz), 40.90 (C P, d, JPC ¼ 125 Hz), 77.06 and 79.35 (2C), 89.04
(C C-NH2), 127.52 (Cipso, d, JPC ¼ 90.2 Hz), 129.38(Cmeta, d, JPC ¼ 11.6 Hz),
1
3
=
132.03 (Cpara), 133.88 (Cortho, d, JPC ¼ 9.9 Hz), 151.64 (C C-NH2), 152.74 and
2
=
2
3
=
=
=
161.25 (C O), 170.95 (C O, d, JPC ¼ 15.3 Hz), 173.03 (C O, d, JPC ¼ 11.3 Hz)
ppm. 31P NMR (d6-DMSO): d 20.85 ppm.
Dimethyl-2-(6-amino-2,4-dihydroxo-pyridin-5-yl)-3-(triphenyl-k5-
phosphanylidene)succinate (7a). White power; yield (88%); mp 185–187 ꢁC; IR
(KBr) (nmax cmꢀ1): 3345 (NH2), 1733, 1688 (C O). Analyst: calcd. for
C28H26N3O6P: C, 63.27; H, 4.93; N, 7.91%. Found: C, 63.39; H, 5.08; N, 7.78%.
=
1
MS (m=z, %): 531 (Mþ, 5). H NMR (500 MHz, d6-DMSO): d 3.05 and 3.65 (6H,
3
2 s, 2OCH3), 4.82 (1H, d, JHP ¼ 16 Hz, CH), 7.60 (1H, s, NH), 7.89 (1H, s, NH),
7.60–7.90 (15H, m, aromatic), 10.98 (2H, s, NH2).13C NMR (125.7 MHz, d6-
1
=
DMSO): d 40.08 (C P, d, JPC ¼ 125 Hz), 50.04 and 52.56 (2OCH3), 58.48 (CH,
2
1
d, JPC ¼ 16.2 Hz), 100.77 (C C-NH2), 125.35 (Cipso, d, JPC ¼ 91.2 Hz), 129.30
=
(Cmeta, d, JPC ¼ 11.3 Hz), 132.72 (Cpara), 133.07 (Cortho, d, JPC ¼ 9.0 Hz), 143.07
3
2
3
=
=
=
(C C-NH2), 150.32 and 150.39 (2C O), 169.54 (C O, d, JPC ¼ 12.5 Hz),
170.67(C O) ppm. 31P NMR (d6-DMSO): d 24.29 ppm.
=
Di-tert-butyl-2-(6-amino-2,4-dihydroxo-pyridin-5-yl)-3-(triphenyl-k5-
phosphany lidene)succinate (7b). White power; yield (70%); mp 180–182 ꢁC; IR
(KBr) (nmax cmꢀ1): 3345 (NH2), 1722, 1692 (C O). Analyst: calcd. for
C34H38N3O6P: C, 66.33; H, 6.22; N, 6.83%. Found: C, 66.42; H, 6.07; N, 6.70%.
=
MS (m=z, %): 615 (Mþ, 7). 1H NMR (500 MHz, d6-DMSO): d 1.43 and 1.45
3
(18H, 2 s, 6CH3), 4.72 (1H, d, JHP ¼ 16.0 Hz, CH), 7.59 (1H, s, NH), 7.48–7.67
(15H, m, aromatic), 7.91 (1H, s, NH), 11.02 (1H, s, NH2). 13C NMR (125.7 MHz,
1
=
d6-DMSO): d 28.09 and 28.21 (6CH3), 40.10 (C P, d, JPC ¼ 125 Hz), 59.37 (CH,
2
d, JPC ¼ 16.8 Hz,), 77.33 and 81.04 (2C), 100.65 (C C-NH2), 126.35 (Cipso, d,
=
1JPC ¼ 91.5 Hz), 129.33 (Cmeta, d, JPC ¼ 11.1 H,), 130.78 (Cpara), 131.75 (Cortho
,
3
d,2JPC ¼ 9.1 Hz), 150.73 (C C-NH2), 151.95 and 164.75 (2C O), 169.12 (C O, d,
=
=
=
JPC ¼ 12.8 Hz), 170.83 (C O) ppm. 31P NMR (d6-DMSO): d 24.08 ppm.
2
=

6-AMINOURACIL
2839
ACKNOWLEDGMENTS
We gratefully acknowledge financial support from the Research Council of Islamic
Azad University of Yazd and the Islamic Azad University of Zahedan of Iran.
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