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

Craig Keene, László Kürti

Research output: Contribution to journalArticle

5 Citations (Scopus)

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.

Original languageEnglish (US)
Article numberSS-2013-C0260-FA
Pages (from-to)1719-1729
Number of pages11
JournalSynthesis (Germany)
Volume45
Issue number13
DOIs
StatePublished - 2013

Fingerprint

Naphthol
2-Naphthylamine
Triazoles
Imines
Acids
2-nitronaphthalene
2-methylbenzaldehyde
2-naphthol

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

Cite this

Regiospecific synthesis of novel cyclic nitrostyrenes and 3-substituted 2-nitronaphthalenes. / Keene, Craig; Kürti, László.

In: Synthesis (Germany), Vol. 45, No. 13, SS-2013-C0260-FA, 2013, p. 1719-1729.

Research output: Contribution to journalArticle

Keene, Craig ; Kürti, László. / Regiospecific synthesis of novel cyclic nitrostyrenes and 3-substituted 2-nitronaphthalenes. In: Synthesis (Germany). 2013 ; Vol. 45, No. 13. pp. 1719-1729.
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