4-(1-Methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones: synthesis, anti-inflammatory effect and in silico approaches

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Luc Van Meervelt,
• Do Thi Thao and
• Nguyen Minh Thong

Beilstein J. Org. Chem. 2025, 21, 817–829, doi:10.3762/bjoc.21.65

• , Vietnam Academy of Science and Technology (VAST), Hanoi 10072, Vietnam 10.3762/bjoc.21.65 Abstract Pyrrolidine-2,3-diones are important intermediates in the synthesis of numerous nitrogen-containing heterocycles which possess a broad spectrum of biological and pharmacological activities. In this article

• , we report the synthesis of 4-(1-methylamino)ethylidene-1,5-disubstituted pyrrolidine-2,3-diones via a reversible transimination reaction between Schiff’ base (C=N) linkage-containing pyrrolidine-2,3-dione derivatives and methylamine with yields of 80 to 92%. In addition to nuclear magnetic resonance

• derivatives; iNOS; pyrrolidine-2,3-dione derivatives; pyrrolidine-2,3-diones; pyrrolidine-2,3-diones targeting reversible transimination reaction; Introduction Nitric oxide (NO) is an important signaling molecule in numerous physiological processes such as neuronal tranmission, immue response, inflammatory

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• enamine derivatives. As compared to glacial acetic acid [42], ethanol has showed to be the best solvent for the synthesis of these pyrrolidine-2,3-diones and a dramatic increase in the yield of the desired products was also observed. In addition, understanding of the reaction mechanism at the molecular

• (kcal·mol−1) at the B3LYP/6-311++G(2d,2p)// B3LYP/6-31+G(d,p) level of theory. Optimization of the reaction conditions for the synthesis of compound 10aa. Synthesis of a library of 1,4,5-trisubstituted pyrrolidine-2,3-diones. Supporting Information Supporting Information File 188: Experimental part

Organocatalytic asymmetric Michael/acyl transfer reaction between α-nitroketones and 4-arylidenepyrrolidine-2,3-diones

• Chandrakanta Parida and
• Subhas Chandra Pan

Beilstein J. Org. Chem. 2021, 17, 1447–1452, doi:10.3762/bjoc.17.100

• ). Finally, nitroketone 2n with a cyclohexyl group was engaged in the reaction and a moderate enantioselectivity was detected for product 3n (Table 2, entry 14). In the next step, we investigated the scope of the reaction of substrate 2a with a variety of pyrrolidine-2,3-diones 1 having different benzylidene

• the reaction with 1a. Scope of pyrrolidine-2,3-diones 1 in the reaction with 2a. Supporting Information Supporting Information File 172: Experimental part.

• -2,3-diones 1d–f were employed in the reaction and mixed results were obtained. Although product 3q having a 4-fluorophenyl-substitution was isolated in 80% yield and 84% ee, slightly decreased enantioselectivities were obtained for the corresponding 4-chloro- (3r, 70% ee) and 4-bromophenyl (3s, 76% ee