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Synlett 2004(13): 2357-2358  
DOI: 10.1055/s-2004-832811
LETTER
© Georg Thieme Verlag Stuttgart · New York

Efficient Microwave Enhanced Synthesis of 4-Thiazolidinones

Veeresa Gududurua, Viet Nguyena, James T. Daltonb, Duane D. Miller*a
a Department of Pharmaceutical Sciences, College of Pharmacy, University of Tennessee, Memphis, TN 38163, USA
Fax: +1(901)4483446; e-Mail: dmiller@utmem.edu;
b Division of Pharmaceutics, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA
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Publication History

Received 14 May 2004
Publication Date:
08 September 2004 (online)

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Abstract

A microwave-enhanced, rapid, three-component one-pot condensation method has been developed for the synthesis of 4-thiazolidinones using environmentally benign solvent ethanol in open vessels at atmospheric pressure. Applying this methodology ten different 4-thiazolidinones were synthesized in good yields.

Key words

microwave - heterocycles - condensation - 4-thiazolidinones - synthesis

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8

Typical Procedure for the Synthesis of 4-Thiazolidinones: A mixture of glycine methyl ester hydrochloride (1a, 0.50 g, 4.00 mmol), aldehyde (2e, 1.66 g, 8.30 mmol), mercaptoacetic acid (0.83 mL, 12.00 mmol), diisopropylethylamine (0.85 mL, 4.83 mmol), and molecular sieves (4 Å, 0.10 g) in EtOH (10 mL) was irradiated with microwaves (power: 100 W) at 120 °C for 30 min, following which the sample was cooled using compressed air. The reaction mixture was diluted with CHCl3 (75 mL), sequentially washed with sat. NaHCO3, H2O, brine, dried (Na2SO4) and solvent was removed in vacuo to get crude product that was purified by column chromatography (silica gel, hexanes-EtOAc) to afford 4e (1.00 g, 80%). 1H NMR (300 MHz, CDCl3): δ = 2.85-2.86 (m, 1 H), 2.92 (s, 6 H), 3.50-3.63 (s, 3 H), 3.83 (br s, 2 H), 4.64 (d, J = 17.1 Hz, 1 H), 6.67 (br s, 0.6 H), 7.07 (br s, 0.7 H), 7.34 (d, J = 9.0 Hz, 1 H), 7.55 (d, J = 3.3 Hz, 2 H), 7.90 (br s, 1 H), 8.31 (m, 1 H). 13C NMR (300 MHz, CDCl3): δ = 31.94, 43.75, 44.53, 51.76, 58.47, 76.72, 112.97, 121.63, 122.69, 124.83, 124.94, 126.18, 131.33, 168.09. MS (ESI): m/z = 345 [M + H].