Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study DOI Creative Commons
Agnieszka Łapczuk-Krygier, Mar Ríos‐Gutiérrez

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 85 - 85

Published: Dec. 29, 2024

In this study, we investigated the [3+2] cycloaddition reaction of CF3CN (TFAN) with nitrilimine (NI) to produce 1,2,4-triazole and compared resulting isomers. We determined preferred pathway by examining electrophilic nucleophilic properties substrates, performing thermodynamic calculations for individual pathways, comparing them experimental results.

Language: Английский

Unraveling the mechanism, regioselectivity, and stereoselectivity of [3 + 2] cycloaddition reactions for anticancer spirooxindole derivatives: A density functional theory study DOI

Khadija Zaki,

Mohamed Ouabane,

Abdelouahid Sbai

et al.

Computational and Theoretical Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 115086 - 115086

Published: Jan. 1, 2025

Language: Английский

Citations

0
Synthesis of bis(het)aryl systems via domino reaction involving (2E,4E)-2,5-dinitrohexa-2,4-diene: DFT mechanistic considerations DOI
Karolina Kula, Radomir Jasiński

Chemistry of Heterocyclic Compounds, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 20, 2025

Language: Английский

Citations

0
Conformer-Specific Differences in Solid-Phase Emission of Pyridoxal 5’-Phosphate Hydrazones Containing Heteroaromatic Cycles DOI

Daniil N. Yarullin,

Sofia O. Slavova,

Ekaterina Abramova

et al.

Optical Materials, Journal Year: 2024, Volume and Issue: unknown, P. 116593 - 116593

Published: Dec. 1, 2024

Language: Английский

Citations

0
Synthesis of Novel Benzofuran Spiro-2-Pyrrolidine Derivatives via [3+2] Azomethine Ylide Cycloadditions and Their Antitumor Activity DOI Open Access
Bo‐Wen Pan, Tao Wang,

Liangliang Zheng

et al.

International Journal of Molecular Sciences, Journal Year: 2024, Volume and Issue: 25(24), P. 13580 - 13580

Published: Dec. 19, 2024

A synthetic strategy of a three-component spiro-pyrrolidine compound based on benzofuran via an [3+2] azomethine ylide cycloaddition reaction is reported herein. Under mild optimal conditions, this can quickly produce potentially bioactive compounds with wide range substrates, high yield, and simple operation. The desired products were obtained yield 74–99% diastereomeric ratio (dr) >20:1. Subsequently, the inhibitory effects cell viability human cancer line HeLa mouse CT26 evaluated. Compounds 4b (IC50 = 15.14 ± 1.33 µM) 4c 10.26 0.87 showed higher antiproliferative activities against cells than cisplatin 15.91 1.09 µM); 4e 8.31 0.64 4s 5.28 0.72 exhibited better 10.27 0.71 µM). introduction electron-donating substituents was beneficial to cells. Molecular docking simulations revealed that may exert corresponding bioactivities by binding antitumor targets through hydrogen bonds, providing new approach for discovering spiro-heterocyclic drugs.

Language: Английский

Citations

0
Mechanistic Aspects of [3+2] Cycloaddition Reaction of Trifluoroacetonitrile with Diarylnitrilimines in Light of Molecular Electron Density Theory Quantum Chemical Study DOI Creative Commons
Agnieszka Łapczuk-Krygier, Mar Ríos‐Gutiérrez

Molecules, Journal Year: 2024, Volume and Issue: 30(1), P. 85 - 85

Published: Dec. 29, 2024

In this study, we investigated the [3+2] cycloaddition reaction of CF3CN (TFAN) with nitrilimine (NI) to produce 1,2,4-triazole and compared resulting isomers. We determined preferred pathway by examining electrophilic nucleophilic properties substrates, performing thermodynamic calculations for individual pathways, comparing them experimental results.

Language: Английский

Citations

0