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DOI: 10.1055/s-0028-1087952
An Easy One-Pot Synthesis of Tetrasubstituted 3-Alkynylpyrroles via Multicomponent Coupling Reaction
Publikationsverlauf
Publikationsdatum:
24. Februar 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.
 
    