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5-Aza-adenine Derivatives for Crop-Protection: Multicomponent Synthesis, Experimental and Theoretical Structural
Lin Yuing Tan1, Felicia Phei Lin Lim1, Sheryn Wong1
1School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan, 47500, Malaysia.
Chempluschem
|June 26, 2024
Summary
A new microwave-assisted synthesis rapidly produces novel triazolotriazine compounds. Some derivatives show potent herbicidal activity, offering potential for agricultural applications.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Computational Chemistry
Background:
- Development of efficient synthetic routes for heterocyclic compounds is crucial for drug discovery and agrochemical research.
- Triazolotriazine scaffolds are of interest due to their diverse biological activities.
- Need for rapid, high-yielding, and purification-friendly synthetic methodologies.
Purpose of the Study:
- To develop a novel, rapid, and catalyst-free microwave-assisted synthesis for 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazine-2-propanamides.
- To investigate the structural and electronic properties of the synthesized compounds using spectroscopic and crystallographic methods.
- To evaluate the synthesized compounds for potential insecticidal, fungicidal, and herbicidal activities.
Main Methods:
- Microwave-assisted three-component, catalyst-free synthesis involving cyanamide, trimethyl orthoformate, and 3-(5-amino-1H-1,2,4-triazol-3-yl)propanamides.
- Characterization using dynamic Nuclear Magnetic Resonance (NMR) spectroscopy and X-ray crystallography.
- Computational analysis using Density Functional Theory (DFT) and Quantum Theory of Atoms in Molecules (QTAIM) methods.
Main Results:
- Successful synthesis of 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazine-2-propanamides in 5-10 minutes with high purity.
- Chromatography-free isolation and purification demonstrated practical utility.
- X-ray crystallography of a representative compound revealed a C-shaped conformation and significant π-electron localization.
- Computational studies elucidated key intermolecular interactions (hydrogen bonding, π-stacking) governing molecular packing.
- Screening identified compounds with potent herbicidal activity against Matricaria inodora.
Conclusions:
- A highly efficient and practical microwave-assisted synthetic route for triazolotriazine derivatives has been established.
- Detailed structural and computational analyses provide insights into molecular conformation and interactions.
- The identified herbicidal activity highlights the potential of these compounds as agrochemicals.
