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6-Nitro-1,2,3,4-tetrahydroquinolines by a tandem reductive amination-SNAr reaction

✍ Scribed by Richard A. Bunce; Takahiro Nago

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
433 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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A tandem reductive amination‐S~N~Ar reaction has been developed for the synthesis of 6‐nitro‐1,2,3,4‐tetrahydroquinolines. Treatment of 4‐(2‐fluoro‐5‐nitrophenyl)‐2‐butanone or 3‐(2‐fluoro‐5‐nitrophenyl)‐propanal with primary amines and sodium cyanoborohydride in methanol at room temperature provided good to excellent yields of the substituted tetrahydroquinolines. The reaction proceeded best with the ketone substrate using primary amines that were unbranched at the α‐carbon. The aldehyde also produced the target heterocycles, but these were accompanied by 10‐15% of the uncyclized side chain reductive amination products.

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