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(±)‐1,2‐Dialkyl‐5‐nitro‐2,3‐dihydro‐1 H ‐indoles by a tandem reductive amination‐S N Ar reaction
Author(s) -
Bunce Richard A.,
Nago Takahiro,
White Brian
Publication year - 2009
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.82
Subject(s) - chemistry , sodium cyanoborohydride , reductive amination , tandem , steric effects , medicinal chemistry , methanol , nitro , ketone , amination , cascade reaction , primary (astronomy) , organic chemistry , catalysis , materials science , alkyl , physics , astronomy , composite material
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).