Herein, we disclose a two-step, practical, regiospecific and readily scalable benzannulation protocol for the preparation of novel 3-alkyl/aryl substituted 2-nitronaphthalenes. Addition of a b-nitrostyrene or nitroalkene to a solution of freshly prepared lithiated o-tolualdehyde tert-butyl imine first leads to the formation of a nitronate, viarapid 1,4-addition, then an intramolecular aza-Henry reaction takes place to afford a six-membered carbocycle. Subsequent treatment of the reaction mixture with aqueous acid affords novel substituted cyclic nitrostyrenes that can be conveniently aromatized via a one-pot radically-induced bromination/ elimination sequence to furnish the corresponding 3-alkyl/aryl-2-nitronaphthalenes in excellent yields. The straightforward synthesis of 2-aminonaphthalenes, substituted BINAMs, 2-naphthols as well as tricyclic fused 1,2,3-triazoles are also described.

Regiospecific synthesis of novel cyclic nitrostyrenes and 3-substituted-2-nitronaphthalenes

247th National Meeting (2014)

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