Easy Preparation Method for 2-Thioxopyrrolidine Derivatives Including 3-Hydroxy- methylene-2-thioxopyrrolidine, an Antimicrobial Degradation Product of Radish Pungent Principle, via (E,Z)-4-Ylethoxy-3-butenyl Isothiocyanate.
An easy preparation method was developed for 3-hydroxymethylene-2-thioxopyrrolidine (TPC), an antimicrobial degradation product of radish pungent principle. The key intermediate, 4- methoxy-3-butenyl-isothiocyanate (MBI), which was prepared from 3-cyanopropionaldehyde dimethyl acetal in 3 reaction steps, was easily converted to TPC in acidic (pH 3.0-4.0) aqueous media. In methanol or ethanol with a few drops of acetic acid, MBI afforded corresponding 3-(α,α-dialkoxy)methyl-2-thioxopyrrolidines as the major products.
a Department of Bioproductive Science , Faculty of Agriculture , 350, Mine, Utsunomiya 321 , Japan.
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Matsuoka
a Department of Bioproductive Science , Faculty of Agriculture , 350, Mine, Utsunomiya 321 , Japan.
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Uda
a Department of Bioproductive Science , Faculty of Agriculture , 350, Mine, Utsunomiya 321 , Japan.
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Mitani
a Department of Bioproductive Science , Faculty of Agriculture , 350, Mine, Utsunomiya 321 , Japan.|b Weed Science Center, Utsunomiya University , 350, Mine, Utsunomiya 321 , Japan.
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Yoneyama
a Department of Bioproductive Science , Faculty of Agriculture , 350, Mine, Utsunomiya 321 , Japan.
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Maeda
2-thioxopyrrolidine derivative; 4-methoxy-3-butenyl isothiocyanate; easy preparation