Azomethines based on ethyl 4-formyl-3,5-dimethyl-1H-pyrrole-2-carboxylate, its biological activity and reaction with thioglycolic acid

Mikhedkina, Olena I.; Ananieva, Valeriia V.; Sakhno, Yana I.; Melnyk, Igor I.; Vereshchak, Vladyslav O.; Osolodchenko, Tetiana P.; Shishkina, Svitlana V.; Tsygankov, Alexander V.; Chebanov, Valentyn A.

doi:10.1007/s10593-023-03215-w

Cited by 1 publication

(2 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is known that the Ugi-4CR proceeds through the formation of an azomethine (Schiff base) in the first stage [ 39 – 40 ]. Therefore, considering the results of our previous work [ 39 ] on the nature and properties of azomethines based on β-chlorovinylaldehyde 1 ( Figure 1 ), we decided to study the possibility of using the three-component Ugi reaction (Ugi-3CR) with preliminary synthesis of azomethines 9a – c ( Table 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…As our previous studies have shown, azomethines based on aromatic amines and substituted pyrrolecarbaldehyde [ 40 ] or pyrrolyl-β-chlorovinylaldehyde [ 39 ], contain several frequently encountered motifs in drugs and drug candidates – a pyrrole heterocycle and an azomethine C=N fragment ( Figure 1 ) – and exhibit some biological activity. Thus, Ugi bisamides based on the same aldehydes and amines may also demonstrate biological activity.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Ugi bisamides based on pyrrolyl-β-chlorovinylaldehyde and their unusual transformations

Tsygankov,

Vereshchak,

Savluk

et al. 2024

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

By one-pot four- and three-component Ugi reactions involving convertible isocyanides and unexplored pyrrole-containing β-chlorovinylaldehyde, a small library of 20 bisamides with unusual behavior in post-Ugi transformations was prepared and characterized. Surprisingly, a well-documented approach to obtain peptide-containing carboxylic acids through acid hydrolysis of the convertible isocyanide moiety in the Ugi bisamides proceeded in an unexpected manner in our case, leading to the formation of derivatives of amides of heterylidenepyruvic acid. An optimized synthetic protocol for this transformation was elaborated and a plausible sequence involving the elimination of the 2-chloroacetamide moiety and the conversion of the β-chlorovinyl fragment into a vinyl one is provided.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%