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

doi:10.1021/ol400787y

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

Chemistry

Research output: Contribution to journal › Article

51 Scopus citations

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 language	English (US)
Pages (from-to)	2062-2065
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	8
DOIs	https://doi.org/10.1021/ol400787y
State	Published - Apr 19 2013

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

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10.1021/ol400787y

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

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.",

author = "Coffman, {Keith C.} and Palazzo, {Teresa A.} and Hartley, {Timothy P.} and Fettinger, {James C.} and Tantillo, {Dean J.} and Kurth, {Mark J.}",

year = "2013",

month = apr,

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doi = "10.1021/ol400787y",

language = "English (US)",

volume = "15",

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T1 - Heterocycle-heterocycle strategies

T2 - (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones

AU - Coffman, Keith C.

AU - Palazzo, Teresa A.

AU - Hartley, Timothy P.

AU - Fettinger, James C.

AU - Tantillo, Dean J.

AU - Kurth, Mark J.

PY - 2013/4/19

Y1 - 2013/4/19

N2 - 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.

AB - 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.

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