Amination of 5-Spiro-Substituted 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones

• Published in: Molecules (Basel, Switzerland) Vol. 26; no. 23; p. 7179
• Main Authors: Khramtsova, Ekaterina E., Lystsova, Ekaterina A., Khokhlova, Evgeniya V., Dmitriev, Maksim V., Maslivets, Andrey N.
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 26.11.2021; MDPI
• Subjects: Amination; Amines; Antimicrobial agents; Biological effects; carbodiimide; Carbodiimides; Decomposition; Dengue fever; Hydrogen; pyrrole-2-one; Solvents; Staphylococcus infections; Substitutes; Thermal decomposition; thermolysis; Urea; United States > US; Switzerland
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules26237179

The 3-hydroxy-1,5-dihydro-2H-pyrrol-2-one motif is a valuable scaffold in drug discovery. The replacement of the 3-oxy fragment in 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones-based compounds with a 3-amino one (3-amino analogs of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, 3-amino-1,5-dihydro-2H-pyrrol-2-ones) can play a crucial role in their biological effect. Thus, approaches to 3-amino-1,5-dihydro-2H-pyrrol-2-ones are of significant interest. We developed an approach to 5-spiro-substituted 3-amino-1,5-dihydro-2H-pyrrol-2-ones that could not be obtained using previously reported approaches (reactions of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones with amines). The developed approach is based on the thermal decomposition of 1,3-disubstituted urea derivatives of 5-spiro-substituted 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones, which were prepared via their reaction with carbodiimides.