1021389-33-2Relevant academic research and scientific papers
6-Nitro-1,2,3,4-tetrahydroquinolines by a tandem reductive amination-S NAr reaction
Bunce, Richard A.,Nago, Takahiro
, p. 1155 - 1160 (2008/12/21)
(Chemical Equation Presented) A tandem reductive amination-SNAr 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.
Benzo-fused heterocycles and carbocycles by intramolecular SNAr and tandem SN2-SNAr reactions
Bunce, Richard A.,Nago, Takahiro,Sonobe, Nathan,Slaughter, LeGrande M.
, p. 551 - 557 (2008/09/18)
(Chemical Equation Presented) Benzo-fused heterocyclic and carbocyclic systems have been synthesized by intramolecular SNAr and tandem SN2-SNAr 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 SNAr 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 SN2-SNAr 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.
