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Ester- and ketone-substituted (±)-1-alkyl-6-nitro-1,2,3,4-tetrahydroquinolines by a tandem SNAr-Michael reaction

✍ Scribed by Richard A. Bunce; Eric J. Lee

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
281 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image A synthesis of ester‐ and ketone‐substituted (±)‐1‐alkyl‐6‐nitro‐1,2,3,4‐tetrahydroquinolines has been developed from 2‐pentenoates and 2‐penten‐1‐ones substituted at C5 by a 2‐fluoro‐5‐nitrophenyl group. The cyclization involves an S~N~Ar reaction followed by a Michael addition that occurs exo to the final ring. A previously reported version of this annulation proceeded by an initial endo Michael addition (acceptor became part of the final ring) followed by an S~N~Ar ring closure. The current reactions proceed in 82–97% yields in DMSO using primary amines that are unbranched at the α carbon. The synthesis of the reaction substrates as well as process optimization, mechanistic studies to elucidate the reaction chronology and comparisons with the endo Michael variant are presented. J. Heterocyclic Chem., (2010).

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