Synthesis of Novel Substituted 4,6-Dimethoxy-N-phenyl-1,3,5-triazin-2-amine Derivatives and Their Antibacterial and Antifungal Activities

Shinde, Ravindra S.; Salunke, S. D.

doi:10.14233/ajchem.2015.19114

Cited by 5 publications

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“…Certainly, Bpin is not the first IMHB acceptor found in molecules. Nitrogen heterocycles have appeared as part of IMHB networks including C–H···N interactions within heteroarenes. − Pyridines, pyrimidines, and triazines are key motifs of biologically active pharmaceuticals, and therefore, their potential use as steric shields via IMHB drew our attention. − In particular, we became interested in osimertinib, an epidermal growth factor receptor tyrosine kinase inhibitor, which presents a pyrimidine group attached to an indole skeleton . We subjected osimertinib analogue 12 to CHB conditions (Figure ).…”

Section: Results and Discussionmentioning

confidence: 99%

Steric Shielding Effects Induced by Intramolecular C–H···O Hydrogen Bonding: Remote Borylation Directed by Bpin Groups

et al. 2022

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Regioselectivities in catalytic C−H borylations (CHBs) have been rationalized using simplistic steric models and correlations with nuclear magnetic resonance (NMR) chemical shifts. However, regioselectivity can be significant for important substrate classes where none would be expected from these arguments. In this study, intramolecular hydrogen bonding (IMHB) can lead to steric shielding effects that can direct Ircatalyzed CHB regiochemistry. Bpin (Bpin = pinacol boronic ester)/arene IMHB can promote remote borylations of Nborylated anilines, 2-amino-N-alkylpyridine, tetrahydroquinolines, indoles, and 1-borylated naphthalenes. Experimental and computational studies support molecular geometries with the Bpin orientation controlled by a C−H•••O IMHB. IMHB-directed remote CHB appeared operative in the C6 borylation of 3-aminoindazole (seven-membered IMHB) and C6 borylation of an osimertinib analogue where a pyrimidine IMHB creates the steric shield. This study informs researchers to evaluate not only interbut also intramolecular noncovalent interactions as potential drivers of remote CHB regioselectivity.

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