Unusual approach to 3-aryl-2-aminopyridines through a radical mechanism: synthesis and theoretical rationale from quantum mechanical calculations.
Tris(trimethylsilyl)silane and azobis(cyclohexanenitrile) promoted the easy intramolecular arylation of aryl bromopyridine carbamates through a radical [1,6] ipso substitution process. These substrates showed a preference for this type of reaction over the alternative [1,7] addition. The results were rationalized by making use of quantum mechanical calculations and computer graphics.
Departamento de Farmacología, Universidad de Alcalá, E-28871 Alcalá de Henares, Madrid, Spain.
Marta
M
Camacho-Artacho
Valentina
V
Abet
Luis M
LM
Frutos
Federico
F
Gago
Julio
J
Alvarez-Builla
Carolina
C
Burgos
D000631:Aminopyridines / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism
D000631:Aminopyridines; D005609:Free Radicals; C032439:alpha-aminopyridine