Regiospecific Synthesis of Novel Cyclic Nitrostyrenes and 3-Substituted 2-Nitronaphthalenes

Craig Keene; László Kürti

doi:10.1055/s-0033-1338867

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(13): 1719-1729
DOI: 10.1055/s-0033-1338867

feature article

Regiospecific Synthesis of Novel Cyclic Nitrostyrenes and 3-Substituted 2-Nitronaphthalenes

Autor*innen

Craig Keene

Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd, Dallas TX 75390, USA Fax: +1(214)6488856 eMail: laszlo.kurti@utsouthwestern.edu
László Kürti*

Division of Chemistry, Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Blvd, Dallas TX 75390, USA Fax: +1(214)6488856 eMail: laszlo.kurti@utsouthwestern.edu

Abstract

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Abstract

A two-step, practical, regiospecific, and readily scalable benzannulation protocol for the preparation of novel 3-alkyl- and 3-aryl-substituted 2-nitronaphthalenes is disclosed. Addition of a β-nitrostyrene or nitroalkene to a solution of freshly prepared lithiated o-tolualdehyde tert-butyl imine first leads to the formation of a nitronate, via rapid 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 radical-induced bromination and elimination sequence to furnish the corresponding 3-alkyl- or 3-aryl-2-nitronaphthalenes in excellent yields. The straightforward syntheses of 2-aminonaphthalenes, substituted BINAMs, 2-naphthols as well as tricyclic fused 1,2,3-triazoles are also described.

Key words

cyclic nitrostyrene - 2-nitronaphthalene - 2-aminonaphthalene - BINAM - fused triazole

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Referenzen

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