(±)‐1,2‐Dialkyl‐5‐nitro‐2,3‐dihydro‐1H‐indoles by a tandem reductive amination‐SNAr reaction
Journal of Heterocyclic Chemistry2009Vol. 46(4), pp. 629–634
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Abstract
Abstract magnified image A tandem reductive amination‐S N Ar reaction has been applied to the synthesis of (±)‐1,2‐dialkyl‐5‐nitro‐2,3‐dihydro‐1 H ‐indoles. Treatment of a series of 2‐fluoro‐5‐nitrobenzyl ketones with primary amines and sodium cyanoborohydride in methanol at room temperature provided good yields of the target heterocycles. The reaction is sensitive to steric hindrance and proceeds best with less hindered ketone substrates using primary amines that are unbranched at the α carbon. J. Heterocyclic Chem., (2009).
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