Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles

Keith C. Coffman, Vy Duong, Alex L. Bagdasarian, James C. Fettinger, Makhluf J. Haddadin, Mark J. Kurth

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn<sup>0</sup> or Fe<sup>0</sup> dust and HOAc using a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.

Original languageEnglish (US)
Pages (from-to)7651-7657
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number34
DOIs
StatePublished - Dec 1 2014

Keywords

  • Cycloaddition
  • Diversity-oriented synthesis
  • Fused-ring systems
  • Nitrogen heterocycles
  • Oxygen heterocycles
  • Reduction

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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    Coffman, K. C., Duong, V., Bagdasarian, A. L., Fettinger, J. C., Haddadin, M. J., & Kurth, M. J. (2014). Heterocycle-to-heterocycle route to quinoline-4-amines: Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles. European Journal of Organic Chemistry, 2014(34), 7651-7657. https://doi.org/10.1002/ejoc.201403065