Conformational space and vibrational spectra of 2-[(2,4-dimethoxyphenyl)amino]-1,3-thiazolidin-4-one

Abstract

In this work we present the results of a study of the X-ray structure of 2-[(2,4-dimethoxyphenyl)amino]-1,3-thiazolidin-4-one. Using the FTIR spectra in solid state and results of ab initio calculations we explain the issue of the tautomerism of this molecule. The compound is shown to exist as the 2-amino tautomer rather 2-imino tautomer. Here we consider eight possible tautomers. On the basis of the vibrational spectra we can eliminate five possible tautomers, as not existing in the solid state. As the most possible tautomeric form we have found keto 2-amino form.Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-014-2366-6) contains supplementary material, which is available to authorized users.

Thiazole-Bearing 4-Thiazolidinones as New Anticonvulsant Agents

“…Target compounds Ib-Id were obtained in the Knoevenagel reaction condition (Scheme 1), compound Ie was synthesized in one-pot three-component reaction of substituted thiourea, aldehyde and chloroacetic acid [51]. Synthesized 4-thiazolidinones, bearing hydrogen atom on an exocyclic nitrogen atom (N3) can exist in the two tautomeric forms -2-imino-4-thiazolidinones (exocyclic C=N bond) and 2-amino-4thiazolidinones (endocyclic C=N bond) [52,53]. The form of compounds presentation (imino-form) was argued by previous data [51].…”

Thiazolidine‐4‐ones from Thiocarbohydrazides

“…Single crystal from symmetrical and unsymmetrical bis‐thiazolidinones 180a–g as well as 2,5‐disubstituted‐2,5‐diamino thiadiazoles 178a–g were formed via reacting of N , N ′‐disubstituted hydrazinecarbothioamides 176a–g with DMAD, 4a during the intermediate 177a–g and 179a–g (Scheme ) .…”

“…Thiazolidinone is known as biologically active compound. Its presence in penicillin and other related derivatives was the first evidence of its presence in nature . It has been reported that thiazolidin‐4‐one ring has various synthetic pharmaceuticals displaying a broad spectrum of biological activities .…”

“…The substituents in the 2‐, 3‐, and 5‐positions are very different, but substituents attached to the C2‐position greatly influenced in structure and properties . Thus, a few derivatives with C2 and N3 substituted positions, and the presence of electron‐withdrawing group on aromatic ring on C2 position of thiazolin‐4‐one showing varied degrees of inhibition against Gram‐positive and Gram‐negative bacteria giving inhibition as good as the standard drugs used .…”

Utilization of 2(3H)‐Furanone Bearing a Pyrazolyl Side Chain for the Construction of a Variety of Thiazolidinone Derivatives

“…Thiazolidinone derivatives have been used as antitubercular, antimicrobial, anti‐inflammatory, and antiviral agents, especially as anti‐HIV agents. It has been extensively reported that the presence of different moieties at different positions in the thiazolidinone ring enhanced its anti‐microbial activity, may be because of its inhibitory activity of enzyme Mur B which is a precursor acting during the biosynthesis of peptidoglycan . Numerous reports had appeared in the literature dealing with their chemistry and pharmacological uses .…”