Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones

Keith C. Coffman, Teresa A. Palazzo, Timothy P. Hartley, James C. Fettinger, Dean J. Tantillo, Mark J. Kurth

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-, and 3,4-bis(2-nitrophenyl) isoxazoles, chemoselective heterocyclization gives quinolin-4(1H)-ones, and 4-aminoquinolines, exclusively.

Original languageEnglish (US)
Pages (from-to)2062-2065
Number of pages4
JournalOrganic Letters
Volume15
Issue number8
DOIs
StatePublished - Apr 19 2013

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Isoxazoles
Indoles
quinoline
indoles
methodology
4-aminoquinoline

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Coffman, K. C., Palazzo, T. A., Hartley, T. P., Fettinger, J. C., Tantillo, D. J., & Kurth, M. J. (2013). Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones. Organic Letters, 15(8), 2062-2065. https://doi.org/10.1021/ol400787y

Heterocycle-heterocycle strategies : (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones. / Coffman, Keith C.; Palazzo, Teresa A.; Hartley, Timothy P.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.

In: Organic Letters, Vol. 15, No. 8, 19.04.2013, p. 2062-2065.

Research output: Contribution to journalArticle

Coffman, KC, Palazzo, TA, Hartley, TP, Fettinger, JC, Tantillo, DJ & Kurth, MJ 2013, 'Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones', Organic Letters, vol. 15, no. 8, pp. 2062-2065. https://doi.org/10.1021/ol400787y
Coffman, Keith C. ; Palazzo, Teresa A. ; Hartley, Timothy P. ; Fettinger, James C. ; Tantillo, Dean J. ; Kurth, Mark J. / Heterocycle-heterocycle strategies : (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones. In: Organic Letters. 2013 ; Vol. 15, No. 8. pp. 2062-2065.
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