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DOI: 10.1055/s-0028-1087952
An Easy One-Pot Synthesis of Tetrasubstituted 3-Alkynylpyrroles via Multicomponent Coupling Reaction
Publication History
Publication Date:
24 February 2009 (online)

Abstract
A series of tetrasubstituted 3-alkynylpyrroles were synthesized via a three-component reaction of imines, phenylacetylene, and dialkylzinc. This method provided a new strategy for preparing tetrasubstituted 3-alkynylpyrroles which can be converted into more complex molecules.
Key words
multicomponent reactions - pyrroles - tetrasubstituted 3-alkynylpyrroles
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References and Notes
The CCDC number: 706290.
16
General Procedure
for the Preparation of Imines
To a round-bottomed
flask containing the amine (10 mmol) in toluene (20 mL) was added
anhyd Na2SO4 (50 mmol). The mixture was stirred,
and then ethyl glyoxalate (12 mmol) was added slowly. After the
reaction was completed (about 1 h, monitored by TLC), Na2SO4 was
removed by filtration, and toluene was distilled under reduced pressure
to yield the crude imine (95% yield), which was used for
the next step without purification.
General
Procedure for the Preparation of Pyrrole Derivatives
To
a flask containing phenylacetylene (6 mmol), a 1.2 M solution of
Me2Zn in toluene (6 mmol) was added at r.t. The resulting
solution was stirred for 1 h, and then the imine
(1 mmol)
in toluene (1 mL) was added at the same temperature. The reaction
mixture was stirred for 5 h. After the reaction was completed (monitored
by TLC), it was quenched by addition of H2O (5 mL). The
mixture was diluted with Et2O, stirred for 5 min, and
then filtered through Celite. The collected filtrate was separated,
and the aqueous phase was extracted with Et2O (3 × 3
mL). The combined organic phases were washed with brine and dried
over Na2SO4. After removal of the solvent
under reduced pressure, the crude product was purified by flash
column chromatography (eluent: EtOAc-PE, 1:50) to afford
the desired pyrrole products.
2-Methyl-5-phenyl-3-(phenylethynyl)-1-
p
-tolyl-1
H
-pyrrole (1a)
White solid. ¹H
NMR (300 MHz, CDCl3): δ = 2.34 (s,
3 H), 2.43 (s, 3 H), 6.60 (s, 1 H), 7.07-7.10 (d, 2 H),
7.16-7.19 (m, 7 H), 7.32-7.41 (m, 3 H), 7.57-7.60
(d, 2 H). ¹³C NMR (75 MHz, CDCl3): δ = 12.75,
21.63, 85.48, 90.72, 103.35, 111.27, 124.78, 126.47, 127.56, 128.28,
128.50, 130.02, 131.47, 132.93, 134.07, 136.40, 136.51, 137.97.
HRMS:
m/z calcd for
C26H21N [M+]:
347.1679; found: 347.1680.