Unexpected Synthesis of Novel 3-Allyl-5-(arylidene)-2-thioxo-thiazolidin-4-ones in Reactions of 3-Allylrhodanine with 2-Arylidene-4-methyl-5-oxopyrazolidinium Ylides

Abstract

The reaction of 3-allylrhodanine with 2-arylidene-4-methyl-5-oxopyrazolidinium ylides proceeded unexpectedly to form novel 3-allyl-5-(arylidene)-2-thioxo-thiazolidin-4-ones 6a–k in good yields. All structures have been formulated on the basis of their spectral (IR, NMR, MS) data and elemental analyses. In addition, the structure of compound 6a was confirmed by means of x-ray crystallographic analysis.

GRAPHICAL ABSTRACT

Keywords:

• 3-Allyl-5-(arylidene)-2-thioxo-thiazolidin-4-ones
• 3-allylrhodanine
• 2-arylidene-4-methyl-5-oxopyrazolidinium ylides
• x-ray diffraction

ACKNOWLEDGMENTS

We thank the National Centre for Scientific and Technical Research (CNRST), Rabat, for providing the NMR and x-ray crystallography of our compounds.

SUPPLEMENTAL MATERIAL

Full characterization data, ¹H and ¹³C NMR spectra, and x-ray crystallographic materials for this article can be accessed on the publisher’s website.