Synlett 2014; 25(14): 2083-2084
DOI: 10.1055/s-0033-1378268
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2-Thioxothiazolidin-4-one (Rhodanine)

Khadijeh Hajibabaei
Department of Chemistry, University of Isfahan, , P.O. Box 81746-73441, Isfahan, Iran   eMail: KhadijehHajibabaei@yahoo.com
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Publikationsverlauf

Publikationsdatum:
31. Juli 2014 (online)

Introduction

2-Thioxothiazolidin-4-one, commonly known as rhodanine, is an organic compound derived from thiazolidine. It is an interesting organic molecule with potential biological activities and pharmacological properties.[1] [2] [3] However, the biological activity of compounds possessing a rhodanine moiety should be considered critically.[4] Rhodanine is commercially available and has been synthesized by the reaction of carbon disulfide, ammonia, and chloroacetic acid (Scheme [1]).[5]

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Scheme 1

Rhodanine has a wide variety of applications in organic syntheses due to the presence of some active centers. Two nucleophilic centers in rhodanine are localized on the sulfur and nitrogen. The methylene part of the rhodanine can act as a nucleophilic center in organic syntheses. An electrophilic center is also associated with the thiocarbonyl carbon atom (Figure [1]).

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Figure 1
 
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