5‐Aza‐adenine Derivatives for Crop‐Protection: Multicomponent Synthesis, Experimental and Theoretical Structural Analysis DOI Creative Commons
Lin Yuing Tan, Felicia Phei Lin Lim, Sheryn Wong

et al.

ChemPlusChem, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 19, 2024

Abstract A microwave‐assisted synthesis of 7‐amino‐1,2,4‐triazolo[1,5‐ a ][1,3,5]triazine‐2‐propanamides was developed using three‐component, catalyst‐free reaction cyanamide and trimethyl orthoformate with 3‐(5‐amino‐1 H ‐1,2,4‐triazol‐3‐yl)propanamides ( 3 ). The tolerated structurally diverse substrates proceeded chemo‐ regio‐selectively, affording the target compounds in high purity 5–10 minutes. convenient chromatography‐free isolation purification products add practicality to this method. structural features prepared were investigated dynamic NMR spectroscopy, X‐ray crystallography computational chemistry calculations. performed on representative compound, 3‐(7‐amino‐1,2,4‐triazolo[1,5‐ ][1,3,5]triazin‐2‐yl)‐ N ‐(4‐benzyl)propanamide 4 l ), showed overall molecular conformation adopt shape letter C. Notable localisation π‐electron density is found within 1,2,4‐triazolo[1,5‐ ][1,3,5]triazine system; relatively short C−NH 2 bond consistent restricted rotation about bond. This study also presents detailed analysis interactions DFT QTAIM methods focus hydrogen‐bonding π‐stacking that influence packing . findings reveal significant roles N−H⋅O, N−H⋅N C−H⋅N interactions, along electrostatically enhanced π⋅π contacts. broad screening for insecticidal, fungicidal herbicidal properties identified several potent activity against Matricaria inodora

Language: Английский

5‐Aza‐adenine Derivatives for Crop‐Protection: Multicomponent Synthesis, Experimental and Theoretical Structural Analysis DOI Creative Commons
Lin Yuing Tan, Felicia Phei Lin Lim, Sheryn Wong

et al.

ChemPlusChem, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 19, 2024

Abstract A microwave‐assisted synthesis of 7‐amino‐1,2,4‐triazolo[1,5‐ a ][1,3,5]triazine‐2‐propanamides was developed using three‐component, catalyst‐free reaction cyanamide and trimethyl orthoformate with 3‐(5‐amino‐1 H ‐1,2,4‐triazol‐3‐yl)propanamides ( 3 ). The tolerated structurally diverse substrates proceeded chemo‐ regio‐selectively, affording the target compounds in high purity 5–10 minutes. convenient chromatography‐free isolation purification products add practicality to this method. structural features prepared were investigated dynamic NMR spectroscopy, X‐ray crystallography computational chemistry calculations. performed on representative compound, 3‐(7‐amino‐1,2,4‐triazolo[1,5‐ ][1,3,5]triazin‐2‐yl)‐ N ‐(4‐benzyl)propanamide 4 l ), showed overall molecular conformation adopt shape letter C. Notable localisation π‐electron density is found within 1,2,4‐triazolo[1,5‐ ][1,3,5]triazine system; relatively short C−NH 2 bond consistent restricted rotation about bond. This study also presents detailed analysis interactions DFT QTAIM methods focus hydrogen‐bonding π‐stacking that influence packing . findings reveal significant roles N−H⋅O, N−H⋅N C−H⋅N interactions, along electrostatically enhanced π⋅π contacts. broad screening for insecticidal, fungicidal herbicidal properties identified several potent activity against Matricaria inodora

Language: Английский

Citations

0