New Aspects of the Reaction of Thioacetamide and N-Substituted Maleimides

New Aspects of the Reaction of Thioacetamide and N-Substituted Maleimides

N-Arylmaleimides are universal substrates for the synthesis of various heterocyclic compounds with a wide spectrum of biological activity. However, their reactions with thioacetamides have not been comprehensively studied. We studied the reactions of thioacetamide with N-arylmaleimides under various...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Vol. 27; no. 24; p. 8800
Main Authors: Aseeva, Yulia V, Stolpovskaya, Nadezhda V, Vandyshev, Dmitriy Y, Sulimov, Vladimir B, Prezent, Mikhail A, Minyaev, Mikhail E, Shikhaliev, Khidmet S
Format: Journal Article
Language:English
Published: Switzerland MDPI AG 01-12-2022
MDPI
Subjects:
Acetates
Acetic acid
Acids
Biological activity
Boiling
Catalytic converters
Diels-Alder reaction
Dioxane
Heterocyclic compounds
Hydrogen
Hydrogen sulfide
Maleimides - chemistry
N-alkylmaleimide
N-arylmaleimide
nucleophilic addition
Organic acids
Pyridine
Pyridines
Pyridines - chemistry
Reagents
recyclization
Resveratrol
Spectral analysis
Spectrum analysis
Thioacetamide
X-Ray Diffraction
United States
United Kingdom
Russia
N-arylmaleimide
thioacetamide
pyrrolo[3,4-c]pyridin
3,3′-thiobis(1-alkylpyrrolidine-2,5-dione)
recyclization
epithiopyrrolo[3,4-c]pyridin
3,3′-thiobis(1-arylpyrrolidine-2,5-dione)
N-alkylmaleimide
Diels-Alder reaction
nucleophilic addition
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Summary:N-Arylmaleimides are universal substrates for the synthesis of various heterocyclic compounds with a wide spectrum of biological activity. However, their reactions with thioacetamides have not been comprehensively studied. We studied the reactions of thioacetamide with N-arylmaleimides under various conditions. We established for the first time that three types of products: epithiopyrrolo[3,4-c]pyridines, pyrrolo[3,4-c]pyridines and 3,3'-thiobis(1-arylpyrrolidine-2,5-diones) can be obtained in different conditions. In all cases, two maleimide molecules are involved in the reaction. 3,3'-Thiobis(1-arylpyrrolidine-2,5-diones) are the major products when the reaction is conducted at boiling in acetic acid. When thioacetamide and N-arylmaleimide are kept in dioxane at 50 °C, epithiopyrrolo[3,4-c]pyridines can be isolated, which, when heated in dioxane, in acetic acid or in methanol in the presence of catalytic amounts of sodium methoxide, are converted into pyrrolo[3,4-c]pyridines by eliminating hydrogen sulfide. The reaction of thioacetamide and N-arylmaleimide in dioxane at boiling temperature with the portioned addition of N-arylmaleimide leads predominantly to the formation of pyrrolo[3,4-c]pyridines. The reaction of thioacetamide with N-alkylmaleimides under all the above conditions leads predominantly to the formation of the corresponding sulfides. The structure of the compounds obtained was characterized by a set of spectral analysis methods and X-ray diffraction (XRD) data.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27248800