Serendipitous synthesis of 2-alkenyl- and 2-aryl-4-thiazolidinones using dithiodiglycolic anhydride

Beng, Timothy K.; Sax, Mckenna; Borg, Claire

doi:10.1039/d2nj03719j

Cited by 2 publications

(2 citation statements)

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“…Interestingly, Beng and co-workers have recently shown that the thiodiglycolic anhydride ( 189 ) does not undergo CCR with imines ( 15 ). Conversely, a formal [3+2] cycloaddition efficiently leads to functionalized 4-thiazolidinones ( 190 , Scheme 56 ) [ 99 ].…”

Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

The Castagnoli–Cushman Reaction

et al. 2023

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Since the first reports of the reaction of imines and cyclic anhydrides by Castagnoli and Cushman, this procedure has been applied to the synthesis of a variety of lactams, some of them with important synthetic or biological interest. The scope of the reaction has been extended to the use of various Schiff bases and anhydrides as well as to different types of precursors for these reagents. In recent years, important advances have been made in understanding the mechanism of the reaction, which has historically been quite controversial. This has helped to develop reaction conditions that lead to pure diastereomers and even homochiral products. In addition, these mechanistic studies have also led to the development of new multicomponent versions of the Castagnoli–Cushman reaction that allow products with more diverse and complex molecular structures to be easily obtained.

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Section: Two-component Castagnoli–cushman Reactions (2c-ccr)mentioning

confidence: 99%

The Castagnoli–Cushman Reaction

et al. 2023

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“…The conventional method for the synthesis of 4‐thiazolidinones involved the reaction of amine, carbonyl compound, and mercaptoacetic acid using different catalysts via a two‐step strategy [16] ( route a , Figure 5). The reaction of acid hydrazide with aldehydes afforded corresponding hydrazones, which on further reaction with thioglycolic acid provided 2‐substituted 4‐thiazolidinone analogs [17] ( route b , Figure 5). Esters on reaction with thiosemicarbazide afforded hydrazine carbothioamides, which undergo heterocyclization with chloroacetic acid in the presence of sodium acetate to get thiazolidin‐4‐one derivatives [18] ( route c , Figure 5).…”

Section: Introductionmentioning

confidence: 99%

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

Singh,

Sindhu,

Kumar

et al. 2023

ChemistrySelect

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Thiazolidinone scaffold has become a promising scaffold when it comes to therapeutic importance, and researchers are quite interested in it because of its wide range of applications in the different fields of chemistry. The capacity of this nucleus to interact with a variety of biological targets, including the peroxisome proliferator‐activated receptor (PPAR), protein tyrosine phosphatase 1B, aldose reductase, α‐glucosidase, and α‐amylase, has led to the observation of its antidiabetic effect. α‐Amylase (α‐1,4‐glucan‐4‐glucanohydrolase, EC 3.2.1.1) is one of the most important industrial endoamylases capable of hydrolyzing the internal α‐1,4‐glycosidic bonds in polysaccharides with net retention of α‐anomeric configuration in low molecular weight products, such as glucose, maltose, and maltotriose units. The inhibitors of α‐amylase have the ability to lower endogenous activity, which is crucial for the management of agricultural pests as well as the treatment and prevention of human disorders. In the present review, we attempted to compile the most recent studies on thiazolidinone‐based α‐amylase inhibitors, investigate their therapeutic potential in treating diabetes, comprehend the relationships between structure and activity, offer suggestions for future research and translation of these findings into clinical applications. This comprehensive review strives to be a valuable resource for researchers, medicinal chemists, and healthcare professionals involved in developing and applying novel therapeutics for treating metabolic disorders.

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Serendipitous synthesis of 2-alkenyl- and 2-aryl-4-thiazolidinones using dithiodiglycolic anhydride

Abstract: Dithiodiglycolic anhydride undergoes an efficient formal cycloaddition with imines to afford functionalized 4-thiazolidinones, without complications arising from the anhydride-imine reaction or the sulfa-Michael reaction (in the case of 1,3-azadienes).

Cited by 2 publications

References 85 publications

The Castagnoli–Cushman Reaction

The Castagnoli–Cushman Reaction

α‐Amylase Inhibitors Based on Thiazolidinone Skeleton: A Promising Approach in Diabetes Management

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