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Benzo‐fused heterocycles and carbocycles by intramolecular S N Ar and tandem S N 2‐S N Ar reactions
Author(s) -
Bunce Richard A.,
Nago Takahiro,
Sonobe Nathan,
Slaughter Legrande M.
Publication year - 2008
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.5570450239
Subject(s) - chemistry , intramolecular force , yield (engineering) , medicinal chemistry , tandem , benzylamine , bromide , dimethylformamide , methylamine , michael reaction , sodium hydride , stereochemistry , organic chemistry , catalysis , materials science , metallurgy , composite material , solvent
Benzo‐fused heterocyclic and carbocyclic systems have been synthesized by intramolecular S N Ar and tandem S N 2‐S N Ar reactions. Treatment of 3‐(2‐fluoro‐5‐nitrophenyl)‐1‐propanol with sodium hydride in N,N ‐dimethylformamide gave 6‐nitrochroman in 80% yield by an intramolecular S N Ar reaction. Treatment of 2‐(3‐bromopropyl)‐1‐fluoro‐4‐nitrobenzene with benzylamine in N,N ‐dimethylformamide gave 1‐benzyl‐6‐nitrotetrahydroquinoline in 98% yield by a tandem S N 2‐S N Ar reaction. Finally, in a similar process, reaction of this same bromide with dimethyl malonate under basic conditions gave 1,1‐bis(methoxycarbonyl)‐6‐nitro‐1,2,3,4‐tetrahydronaphthalene in 80% yield. Further studies exploring ring size effects are also presented.