Three-component reaction of triphenylphosphine, dialkyl acetylenedicarboxylate, and 2-aminothiazole or 2-aminobenzothiazole in the presence of arylglyoxals: An efficient one-pot synthesis of highly functionalized pyrroles

Article abstract of DOI:10.1080/00397911.2010.545496

A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives by three-component reaction of dialkyl acetylenedicarboxylates, triphenylphosphine, 2-aminothiazole or 2-aminobenzothiazole in the presence of arylglyoxals is described. The reac

Full text of DOI:10.1080/00397911.2010.545496

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Three-Component Reaction of
Triphenylphosphine, Dialkyl
Acetylenedicarboxylate, and 2-
Aminothiazole or 2-Aminobenzothiazole
in the Presence of Arylglyoxals: An
Efficient One-Pot Synthesis of Highly
Functionalized Pyrroles
Mohammad Anary-Abbasinejad a , Hamidreza Dehghanpour Farashah
b , Alireza Hassanabadi c , Hossein Anaraki-Ardakani d & Nasim
Shams b
a Department of Chemistry, Rafsanjan Vali-e-Asr University,
Rafsanjan, Iran
b Department of Chemistry, Islamic Azad University, Yazd Branch,
Yazd, Iran
c Department of Chemistry, Islamic Azad University, Zahedan Branch,
Zahedan, Iran
d Department of Chemistry, Islamic Azad University, Mahshahr
Branch, Mahshahr, Iran
Accepted author version posted online: 08 Dec 2011.Published
online: 26 Mar 2012.
To cite this article: Mohammad Anary-Abbasinejad , Hamidreza Dehghanpour Farashah , Alireza
Hassanabadi , Hossein Anaraki-Ardakani & Nasim Shams (2012) Three-Component Reaction of
Triphenylphosphine, Dialkyl Acetylenedicarboxylate, and 2-Aminothiazole or 2-Aminobenzothiazole
in the Presence of Arylglyoxals: An Efficient One-Pot Synthesis of Highly Functionalized Pyrroles,
Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic
Chemistry, 42:13, 1877-1884, DOI: 10.1080/00397911.2010.545496
To link to this article: http://dx.doi.org/10.1080/00397911.2010.545496

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Synthetic Communications1, 42: 1877–1884, 2012
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397911.2010.545496
THREE-COMPONENT REACTION OF
TRIPHENYLPHOSPHINE, DIALKYL
ACETYLENEDICARBOXYLATE, AND
2-AMINOTHIAZOLE OR 2-AMINOBENZOTHIAZOLE
IN THE PRESENCE OF ARYLGLYOXALS: AN
EFFICIENT ONE-POT SYNTHESIS OF HIGHLY
FUNCTIONALIZED PYRROLES
Mohammad Anary-Abbasinejad,1 Hamidreza Dehghanpour
Farashah,2 Alireza Hassanabadi,3 Hossein Anaraki-Ardakani,4
and Nasim Shams2
1Department of Chemistry, Rafsanjan Vali-e-Asr University, Rafsanjan, Iran
2Department of Chemistry, Islamic Azad University, Yazd Branch, Yazd,
Iran
3Department of Chemistry, Islamic Azad University, Zahedan Branch,
Zahedan, Iran
4Department of Chemistry, Islamic Azad University, Mahshahr Branch,
Mahshahr, Iran
GRAPHICAL ABSTRACT
Abstract A new and efficient one-pot synthesis of polysubstituted pyrrole derivatives
by three-component reaction of dialkyl acetylenedicarboxylates, triphenylphosphine,
2-aminothiazole or 2-aminobenzothiazole in the presence of arylglyoxals is described.
The reactions were performed in dichloromethane at room temperature and neutral
conditions and afforded good yields of products.
Keywords 2-Aminobenzothiazole; 2-aminothiazole; arylglyoxals; dialkyl acetylenedicar-
boxylates; intramolecular Wittig reaction; multicomponent reaction; pyrrole derivatives;
triphenylphosphine
Received August 20, 2010.
Address correspondence to Alireza Hassanabadi, Department of Chemistry, Islamic Azad
University, Zahedan Branch, P.O. Box 98135-978, Zahedan, Iran. E-mail: ar_hasanabadi@yahoo.com
1877

1878
M. ANARY-ABBASINEJAD ET AL.
INTRODUCTION
Pyrroles are heterocycles of great importance because of their presence in
numerous natural products such as heme, vitamin B12, and various cytochrome
enzymes.[1] Some of the recently isolated pyrrole-containing marine natural products
have been found to exhibit considerable cytotoxicity and function as multidrug-
resistant (MDR) reversal agents.[2] Many of these biologically active compounds
have emerged as chemotherapeutic agents. In addition, polysubstituted pyrroles
are molecular frameworks having immense importance in material science. They
have been employed as antioxidants; antibacterial, ionotropic, antitumor, anti-
inflammatory, and antifungal agents,[3] P38 kinase, prolyl-4-hydroxylase, and
poly(ADP-ribose)polymerase inhibitors; estrogen receptor b selective ligands; AT1-
selective angiotensin II receptor antagonists, and minor groove-recognition
elements.[4] Moreover, they are a highly versatile class of intermediates in the syn-
thesis of natural products as well as in heterocyclic chemistry.[5] Consequently, a
large number of methods have been developed for their synthesis. which include
1,3-dipolar cycloaddition reactions,[6] reductive coupling,[7] and aza-Wittig reac-
tions.[8] These methodologies typically require the preparation of the precursors
prior to cyclization, which can complicate both the synthesis and the structural
modification of the substituted pyrroles. This has stimulated significant interest in
the design of new synthetic routes to pyrroles, including several efficient multicom-
ponent reactions[9–12] and metal-catalyzed routes.[13] Addition reaction between
phosphines and activated carbon–carbon triple bonds is well known to produce a
reactive zwitterionic intermediate, which may be trapped by various electro-
philes.[14–18] Reaction of triphenylphosphine with dimethyl acetylenedicarboxylate
(DMAD) has been studied in the presence of a variety of organic acidic compounds
to trap the zwitterionic intermediate. Trapping of the PPh3-DMAD zwitterion by an
organic acidic compound containing a carbonyl group has been used as an efficient,
one-pot route for the synthesis of a variety of heterocyclic and carbocyclic
compounds.[17–22] Treatment of triphenylphosphine with DMAD in the presence
of primary amines has been reported to produce b-amino phosphoranes 4
(Scheme 1).[18]
Recently we reported the one-pot reaction of these ylides with aryl glyoxals for
the synthesis of substituted N-Aryl pyrroles.[23]
Here we report an extention of this route for the synthesis of polysubstituted
pyrrole derivatives by the three-component reaction of dialkyl acetylenedicarboxy-
lates, triphenylphosphine, and 2-aminothiazole or 2-aminobenzothiazole in the
presence of arylglyoxals. We first prepared ylide 4 by the reaction of triphenylpho-
sphine, DMAD, and 2-aminothiazole by the previously reported procedure.[15]
Scheme 1. Synthesis of 2-aminophosphoranes by reaction of PPh3-DAAD zwitterion with 2-aminothia-
zole or 2-aminobenzothiazole.

HIGHLY FUNCTIONALIZED PYRROLES
1879
When phosphorane 4 was stirred with an equimolar amount of phenylglyoxal in
dichloromethane, a smooth reaction took place. After completion of the reaction
(monitored by thin-layer chromatography, TLC) dimethyl 4-phenyl-1-(thiazol-2-
yl)-1H-pyrrole-2,3-dicarboxylate 6a was obtained in 85% yield. As shown in
Scheme 2, it is reasonable to assume that the Wittig reaction between phosphorane
4 and phenylglyoxal 5 affords intermediate 6, which then cyclizes to dihydropyrrole
intermediate 7 and subsequently loses water to produce pyrrole derivative 6a.
Being successful in this reaction, we decided to investigate the one-pot synthesis
of dimethyl 4-phenyl-1-(thiazol-2-yl)-1H-pyrrole-2,3-dicarboxylate 6a (Scheme 3).
Thus, equimolar amounts of triphenylphosphine, 2-aminothiazole, and DMAD were
mixed in dichloromethane as solvent. After stirring for 1 min at room temperature,
phenylglyoxal was added, and the progress of the reaction was monitored by TLC.
After 24 h, the TLC of the mixture of the reaction showed only the presence of pyr-
role derivative 6a and triphenylphosphine oxide. Silica-gel chromatography afforded
the product 2-aminothiazole 6a in 85% yield. To investigate the scope of the reaction,
2-aminothiazole or 2-aminobenzothiazole was reacted with arylglyoxals, triphenyl-
phosphine, and dialkylacetylenedicarboxylates, and the corresponding pyrroles were
obtained in good yields (Scheme 3).
The structures of compounds 6a–h were deduced from their elemental analyses
and their infrared (IR), 1H NMR, and 13CNMR spectral data. The mass spectrum of
compound 6a displayed the molecular ion peak at m=z ¼ 342 as the base peak. The
500-MHZ 1H NMR spectrum of 6a exhibited three sharp signals at d 3.74, 3.76, and
7.14 ppm for two methoxy groups protons and the proton of pyrrole ring, respec-
tively. Aromatic protons resonated between 7.21 and 7.58 ppm as multiplets. The
13C NMR spectrum of compound 6a showed 15 distinct resonances in agreement
with the proposed structure. The structural assignments made on the basis of the
NMR spectra of compound 6a were supported by its IR spectrum. The ester car-
bonyl groups exhibited strong absorption bands at about 1708 cmꢀ1. In conclusion,
here we report a three-component reaction of dialkyl acetylenedicarboxylate,
Scheme 2. Reaction of 2-aminophosphoranes 4 with arylglyoxals 5 for the synthesis of pyrrole
derivatives 6.

1880
M. ANARY-ABBASINEJAD ET AL.
Scheme 3. Three-component reaction of 2-aminothiazole or 2-aminobenzothiazole, DAADs, and aryl-
glyoxals promoted by PPh3.
2-aminothiazole or 2-aminobenzothiazole, and arylglioxals promoted by triphenyl-
phosphine to produce functionalized pyrrole derivatives in good yields. Not only
is the reaction 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 using a Costech ECS 4010 CHNS-O analyzer
at the analytical laboratory of the Islamic Azad University Yazd branch. Mass spec-
tra were recorded on a Finnigan-MAT 8430 mass spectrometer operating at an
ionization potential of 70 eV. IR spectra were recorded on a Shimadzu IR-470 spec-
1
trometer. H and 13C NMR spectra were recorded on a Bruker DRX-500 Avance
1
spectrometer at 500.1 and 125.8 MHz, respectively. H and 13C NMR spectra were
obtained in solution in CDCl3 using tetramethylsilane (TMS) as internal standard.
Column chromatography was performed with Merck silica gel 60, 230–400 mesh.
The chemicals used in this work were purchased from Fluka (Buchs, Switzerland)
and were used without further purification.
General Procedure for Preparation of Compounds 6a–h
A mixture of dialkyl acetylenedicarboxylate (1 mmol) in dichloromethane
(3 mL) was added dropwise to a magnetically stirred solution of triphenylphosphine

HIGHLY FUNCTIONALIZED PYRROLES
1881
(1 mmol) and 2-aminothiazole or 2-aminobenzothiazole (1 mmol) in dichloro-
methane (10 mL). At room temperature over 2 min. The reaction mixture was then
stirred for 1 min. Arylglyoxal (1 mmol) was added, and the reaction mixture was stir-
red for 24 hs. The solvent was evaporated, and the residue was purified by column
chromatography on silicagel using ethyl acetate–hexane mixture as eluent.
Dimethyl 4-Phenyl-1-(thiazol-2-yl)-1H-pyrrole-2,3-dicarboxylate (6a)
Yellow powder, mp 125–127 ꢁC; IR (KBr) (nmax=cmꢀ1): 1708 (C O). Anal.
=
Calcd. for C17H14N2O4S (342): C, 59.64; H, 4.12; N, 8.18%. Found: C, 59.5; H,
4.2; N, 8.3%. MS, m=z (%): 342 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 3.74 and 3.76 (6H, 2 s, 2 OCH3), 7.14 (1H, s, CH of pyrrole), 7.21–7.37 (6H,
3
m, C6H5 and CH of C3H2NS), 7.58 (1H, d, JHH ¼ 3.4 HZ, CH of C3H2NS) ppm.
13C NMR (125.8 MHZ, CDCl3): d ¼ 52.73 and 52.94 (2 OCH3), 119.81, 122.30,
124.84, 126.90, 127.99, 128.53, 128.99, 132.85, 140.70, 158.83, 161.98 (aromatic),
=
165.73 and 168.46 (2 C O, ester).
Diethyl 4-(4-Chlorophenyl)-1-(thiazol-2-yl)-1H-pyrrole-2,3-
dicarboxylate (6b)
Yellow powder, mp 112–114 ꢁC; IR (KBr) (nmax=cmꢀ1): 1726 (C O). Anal.
calcd. for C19H17ClN2O4S (404): C, 56.36; H, 4.23; N, 6.92%. Found: C, 56.3; H,
4.3; N, 6.8%. MS, m=z (%): 404 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 1.99 (6H, m, 2 OCH2CH3), 4.22 (4H, m, 2 OCH2CH3), 7.14 (1H, s, CH of pyr-
=
3
role), 7.25 (1 H, d, JHH ¼ 3.5 HZ, CH of C3H2NS), 7.27–7.31 (4 H, m, 2 CH of
3
4Cl-C6H4), 7.58 (1 H, d, JHH ¼ 3.5 HZ, CH of C3H2NS) ppm. 13C NMR (125.8
MHZ, CDCl3): d ¼ 14.32, 14.47 (2OCH2CH3), 61.77 and 62.07 (2OCH2CH3),
119.83, 122.15, 124.53, 125.71, 128.99, 129.99, 131.50, 133.93, 140.67, 158.75,
=
160.44 (aromatic), 165.01 and 168.26 (2 C O, ester).
Dimethyl 4-(4-Chlorophenyl)-1-(thiazol-2-yl)-1H-pyrrole-2,3-
dicarboxylate (6c)
Yellow powder, mp 137–139 ꢁC; IR (KBr) (nmax=cmꢀ1): 1723 (C O). Anal.
calcd. for C17H13ClN2O4S (376): C, 54.19; H, 3.48; N, 7.43%. Found: C, 54.3; H,
3.5; N, 7.6%. MS, m=z (%): 376 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 3.73 and 3.76 (6 H, 2 s, 2 OCH3), 7.15 (1H, s, CH of pyrrole), 7.24 (1 H, d,
3JHH ¼ 3.5 HZ, CH of C3H2NS), 7.27–7.30 (4 H, m, 2 CH of 4Cl-C6H4), 7.58 (1
=
3
H, d, JHH ¼ 3.5 HZ, CH of C3H2NS) ppm. 13C NMR (125.8 MHZ, CDCl3):
d ¼ 52.73 and 53.04 (2 OCH3), 119.73, 121.65, 124.53, 125.90, 129.05, 129.98,
=
131.30, 134.02, 140.76, 158.62, 161.03 (aromatic), 165.36 and 168.16 (2 C O, ester).
Diethyl 4-(4-Nitrophenyl)-1-(thiazol-2-yl)-1H-pyrrole-2,3-
dicarboxylate (6d)
Yellow powder, mp 131–133 ꢁC; IR (KBr) (nmax=cmꢀ1): 1726 (C O). Anal.
Calcd. for C19H17N3O6S (415): C, 54.93; H, 4.12; N, 10.12%. Found: C, 54.8; H,
=

1882
M. ANARY-ABBASINEJAD ET AL.
4.3; N, 10.0%. MS, m=z (%): 415 (Mþ., 100). 1H NMR (500 MHZ, CDCl3): d ¼ 1.21
(6H, m, 2 OCH2CH3), 4.29 (4H, m, 2 OCH2CH3), 7.32 (1H, s, CH of pyrrole), 7.35
3
3
(1 H, d, JHH ¼ 3.5 HZ, CH of C3H2NS), 7.59 (2 H, d, JHH ¼ 8.7 HZ, 2CH of
3
4-NO2C6H4), 7.65 (1 H, d, JHH ¼ 3.5 HZ, CH of C3H2NS), 8.21 (2 H, d,
3JHH ¼ 8.7 HZ, 2CH of 4-NO2C6H4) ppm. 13C NMR (125.8 MHZ, CDCl3):
d ¼ 14.29, 14.41 (2OCH2CH3), 61.65 and 62.12 (2OCH2CH3), 119.99, 121.45,
124.23, 124.76, 126.91, 129.21, 139.90, 140.78, 147.46, 158.34, 160.36 (aromatic),
=
164.57 and 168.13 (2 C O, ester).
Dimethyl 4-(4-Nitrophenyl)-1-(thiazol-2-yl)-1H-pyrrole-2,3-
dicarboxylate (6e)
Yellow powder, mp 117–119 ꢁC; IR (KBr) (nmax=cmꢀ1): 1721 (C O). Anal.
calcd. for C17H13N3O6S (387): C, 52.71; H, 3.38; N, 10.85%. Found: C, 52.8; H,
3.2; N, 10.7%. MS, m=z (%): 387 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 3.79 and 3.84 (6 H, 2 s, 2 OCH3), 7.32 (1H, s, CH of pyrrole), 7.33 (1 H, d,
3JHH ¼ 3.5 HZ, CH of C3H2NS), 7.58 (2 H, d, 3JHH ¼ 8.7 HZ, 2CH of 4-NO2C6H4),
=
3
3
7.64 (1 H, d, JHH ¼ 3.5 HZ, CH of C3H2NS), 8.19 (2 H, d, JHH ¼ 8.7 HZ, 2CH of
4-NO2C6H4) ppm. 13C NMR (125.8 MHZ, CDCl3): d ¼ 52.85 and 53.23 (2 OCH3),
119.94, 120.93, 124.12, 124.92, 126.89, 129.38, 139.75, 140.86, 147.47, 158.19, 160.95
=
(aromatic), 164.91 and 168.37 (2 C O, ester).
Dimethyl 1-(Benzo[d]thiazol-2-yl)-4-phenyl-1H-pyrrole-2,3-
dicarboxylate (6f)
Yellow powder, mp 112–113 ꢁC, IR (KBr) (nmax=cmꢀ1): 1722 (C O). Anal.
calcd. for C21H16N2O4S (392): C, 64.27; H, 4.11; N, 7.14%. Found: C, 64.3; H,
4.3; N, 7.3%. MS, m=z (%): 392 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 3.80 and 3.90 (6 H, 2 s, 2 OCH3), 7.31 (1H, s, CH of pyrrole), 7.32–7.58 (7 H,
=
3
3
m, aromatic), 7.83 (1 H, d, JHH ¼ 8 HZ, CH of aromatic), 7.97 (1 H, d, JHH ¼ 8
HZ, CH of aromatic) ppm. 13C NMR (125.8 MHZ, CDCl3): d ¼ 52.65 and 52.23
(2 OCH3), 121.55, 121.99, 123.73, 12386, 126.35, 126.60, 127.37, 127.77, 128.10,
128.82, 128.85, 132.80, 134.88, 150.37, 157.68 (aromatic), 161.52 and 165.18 (2
=
C O, ester).
Dimethyl 1-(Benzo[d]thiazol-2-yl)-4-(4-chlorophenyl)-1H-pyrrole-
2,3-dicarboxylate (6g)
Yellow powder, mp 147–149 ꢁC, IR (KBr) (nmax=cmꢀ1): 1732 (C O). Anal.
calcd. for C21H15ClN2O4S (426): C, 59.09; H, 3.54; N, 6.56%. Found: C, 59.2; H,
3.4; N, 6.6%. MS, m=z (%): 426 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 3.80 and 3.90 (6 H, 2 s, 2 OCH3), 7.23 (1H, s, CH of pyrrole), 7.25–7.53 (6 H,
m, aromatic), 7.96 (1 H, d, 3JHH ¼ 8.3 HZ, CH of aromatic), 8.05 (1 H, d, 3JHH ¼ 8.3
8.3 HZ, CH of aromatic) ppm. 13C NMR (125.8 MHZ, CDCl3): d ¼ 52.66 and 53.32
(2 OCH3), 121.99, 123.43, 123.88, 126.41, 126.76, 127.43, 128.96, 129.23, 129.67,
129.84, 130.29, 131.30, 132.88, 150.47, 156.26 (aromatic), 162.31 and 168.19 (2
=
=
C O, ester).

HIGHLY FUNCTIONALIZED PYRROLES
1883
Diethyl 1-(Benzo[d]thiazol-2-yl)-4-(4-chlorophenyl)-1H-pyrrole-
2,3-dicarboxylate (6h)
Yellow powder, mp 130–132 ꢁC, IR (KBr) (nmax=cmꢀ1): 1716 (C O). Anal.
calcd. for C23H19ClN2O4S (454): C, 60.72; H, 4.21; N, 6.16%. Found: C, 60.8; H,
4.1; N, 6.4%. MS, m=z (%): 454 (Mþ., 100). 1H NMR (500 MHZ, CDCl3):
d ¼ 1.29 (6H, m, 2 OCH2CH3), 4.29 (2H, d,3JHH ¼ 7.2 HZ, OCH2CH3), 4.37 (2H,
=
3
d, JHH ¼ 7.2 HZ, OCH2CH3), 7.29 (1H, s, CH of pyrrole), 7.34–7.87 (6 H, m, aro-
3
3
matic), 7.96 (1 H, d, JHH ¼ 8.3 HZ, CH of aromatic), 8.45 (1 H, d, JHH ¼ 8.3 HZ,
CH of aromatic) ppm.. 13C NMR (125.8 MHZ, CDCl3): d ¼ 14.35, 14.47
(2OCH2CH3), 61.67 and 62.44 (2OCH2CH3), 121.97, 123.29, 123.82, 126.35,
126.76, 127.39, 128.88, 129.22, 129.69, 130.35, 131.30, 131.44, 132.88, 150.47,
=
156.26 (aromatic), 160.36 and 168.18 (2 C O, ester).
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