Unusual Approach to 3-Aryl-2-aminopyridines through a Radical Mechanism: Synthesis and Theoretical Rationale from Quantum Mechanical Calculations†

…, F Gago, J Alvarez-Builla, C Burgos

Index: Abet, Valentina; Nunez, Araceli; Mendicuti, Francisco; Burgos, Carolina; Alvarez-Builla, Julio Journal of Organic Chemistry, 2008 ,  vol. 73,  # 22  p. 8800 - 8807

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Citation Number: 6

Abstract

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.