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

doi:10.1002/ejoc.201403065

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	7651-7657
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	34
DOIs	https://doi.org/10.1002/ejoc.201403065
State	Published - 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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10.1002/ejoc.201403065

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Heterocycle-to-heterocycle route to quinoline-4-amines : Reductive heterocyclization of 3-(2-nitrophenyl)isoxazoles. / Coffman, Keith C.; Duong, Vy; Bagdasarian, Alex L.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.

In: European Journal of Organic Chemistry, Vol. 2014, No. 34, 01.12.2014, p. 7651-7657.

Research output: Contribution to journal › Article › peer-review

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abstract = "A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 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.",

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AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

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AB - A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0 or Fe0 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.

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KW - Diversity-oriented synthesis

KW - Fused-ring systems

KW - Nitrogen heterocycles

KW - Oxygen heterocycles

KW - Reduction

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

Abstract

Keywords

ASJC Scopus subject areas

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