Convergent, regiospecific synthesis of quinolines from o-aminophenylboronates

…, SP Marsden, A Nelson, D House, GG Weingarten

Index: Horn, Joachim; Marsden, Stephen P.; Nelson, Adam; House, David; Weingarten, Gordon G. Organic Letters, 2008 , vol. 10, # 18 p. 4117 - 4120

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Citation Number: 81

Abstract

A direct convergent two-component synthesis of quinolines from α, β-unsaturated ketones and o-aminophenylboronic acid derivatives is reported. The reaction is regiocomplementary to the traditional Skraup− Doebner− Von Miller synthesis and proceeds under basic rather than strongly acidic conditions. Quinolines substituted in the benzenoid ring can be accessed by using substituted o-aminophenylboronates prepared by direct palladium- ...