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Benzo-fused heterocycles and carbocycles by intramolecular SNAr and tandem SN2-SNAr reactions

✍ Scribed by Richard A. Bunce; Takahiro Nago; Nathan Sonobe; Legrande M. Slaughter

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

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✦ Synopsis

Abstract

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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.

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